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Capsaicin

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1910: 503: 368: 2008: 1956: 904: 14638: 899: 1887: 2016: 2000: 894: 889: 1933: 1031: 14857: 1992: 1978: 1864: 49: 1363: 2134:, and is native only to the Americas. Chilies only started to quickly evolve in the past 2 million years into markedly different species. This evolution can be partially attributed to a key compound found in peppers, 8-methyl-N-vanillyl-6-nonenamide, otherwise known as capsaicin. Capsaicin evolved similarly across species of chilies that produce capsaicin. Its evolution over the course of centuries is due to 14867: 40: 14893: 1092: 1034: 2114:
various acyl-CoA products from the branched-chain fatty acid pathway, which is capable of producing a variety of acyl-CoA moieties of different chain length and degrees of unsaturation. All condensation reactions between the products of the phenylpropanoid and branched-chain fatty acid pathway are mediated by capsaicin synthase to produce the final capsaicinoid product.
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mammals pose a risk to the propagation of chilies because their molars grind the seeds of chilies, rendering them unable to grow into new chili plants. As a result, modern chilies evolved defense mechanisms to mitigate the risk of granivorous mammals. While capsaicin is present at some level in every
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Capsaicin is a potent defense mechanism for chilies, but it does come at a cost. Varying levels of capsaicin in chilies currently appear to be caused by an evolutionary split between surviving in dry environments, and having defense mechanisms against fungal growth, insects, and granivorous mammals.
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Painful exposures to capsaicin-containing peppers are among the most common plant-related exposures presented to poison centers. They cause burning or stinging pain to the skin and, if ingested in large amounts by adults or small amounts by children, can produce nausea, vomiting, abdominal pain, and
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Witting E (1822). "Considerations sur les bases vegetales en general, sous le point de vue pharmaceutique et descriptif de deux substances, la capsicine et la nicotianine" [Thoughts on the plant bases in general from a pharmaceutical viewpoint, and description of two substances, capsicin and
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while leucine or valine provide the precursor for the branched-chain fatty acid pathway. To produce capsaicin, 8-methyl-6-nonenoyl-CoA is produced by the branched-chain fatty acid pathway and condensed with vanillylamine. Other capsaicinoids are produced by the condensation of vanillylamine with
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Capsaicin acts as an antifungal agent in four primary ways. First, capsaicin inhibits the metabolic rate of the cells that make up the fungal biofilm. This inhibits the area and growth rate of the fungus, since the biofilm creates an area where a fungus can grow and adhere to the chili in which
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from which it was extracted. John Clough Thresh (1850–1932), who had isolated capsaicin in almost pure form, gave it the name "capsaicin" in 1876. Karl Micko isolated capsaicin in its pure form in 1898. Capsaicin's chemical composition was first determined in 1919 by E. K. Nelson, who also
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formation, which impacts the amount of nutrients that the rest of the fungal body can receive. Thirdly, capsaicin disrupts the structure of fungal cells and the fungal cell membranes. This has consequential negative impacts on the integrity of fungal cells and their ability to survive and
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Capsaicin is a strong irritant requiring proper protective goggles, respirators, and proper hazardous material-handling procedures. Capsaicin takes effect upon skin contact (irritant, sensitizer), eye contact (irritant), ingestion, and inhalation (lung irritant, lung sensitizer). The
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to the brain. By binding to TRPV1 receptors, capsaicin produces similar sensations to those of excessive heat or abrasive damage, such as warming, tingling, itching, or stinging, explaining why capsaicin is described as an irritant on the skin and eyes or by ingestion.
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channel does not respond to capsaicin or related chemicals but mammalian TRPV1 is very sensitive to it. This is advantageous to the plant, as chili pepper seeds consumed by birds pass through the digestive tract and can germinate later, whereas mammals have
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The general biosynthetic pathway of capsaicin and other capsaicinoids was elucidated in the 1960s by Bennett and Kirby, and Leete and Louden. Radiolabeling studies identified phenylalanine and valine as the precursors to capsaicin. Enzymes of the
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Kozukue N, Han JS, Kozukue E, Lee SJ, Kim JA, Lee KR, et al. (November 2005). "Analysis of eight capsaicinoids in peppers and pepper-containing foods by high-performance liquid chromatography and liquid chromatography-mass spectrometry".
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neuralgia was refused. One 2017 review of clinical studies having limited quality found that high-dose topical capsaicin (8%) compared with control (0.4% capsaicin) provided moderate to substantial pain relief from post-herpetic neuralgia,
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Braconnot H (1817). "Examen chemique du Piment, de son principe âcre, et de celui des plantes de la famille des renonculacées" [Chemical investigation of the chili pepper, of its pungent principle , and of that of plants of the family
2037:-methyltransferase (COMT) and their function in capsaicinoid biosynthesis were identified later by Fujiwake et al., and Sukrasno and Yeoman. Suzuki et al. are responsible for identifying leucine as another precursor to the branched-chain 1577:
in 2006 states that "Although hot chili pepper extract is commonly used as a component of household and garden insect-repellent formulas, it is not clear that the capsaicinoid elements of the extract are responsible for its repellency."
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Capsaicin synthesis in chilies places a strain on their water resources. This directly affects their fitness, as it has been observed that standard concentration of capsaicin of peppers in high moisture environments in the seeds and
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Govindarajan VS, Sathyanarayana MN (1991). "Capsicum--production, technology, chemistry, and quality. Part V. Impact on physiology, pharmacology, nutrition, and metabolism; structure, pungency, pain, and desensitization sequences".
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synthesis of growing fungi decreases in relation to the amount of capsaicin present in the growth area. This impacts the fungal cell membrane, and how it is able to reproduce and adapt to stressors in its environment.
9054: 8190: 7925: 2041:. It was discovered in 1999 that pungency of chili peppers is related to higher transcription levels of key enzymes of the phenylpropanoid pathway, phenylalanine ammonia lyase, cinnamate 4-hydroxylase, caffeic acid 2203:
part of the pepper, the chemical has its highest concentration in the tissue near the seeds within chilies. Birds are able to eat chilies, then disperse the seeds in their excrement, enabling propagation.
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may have led to increasing capsaicin production because it makes the plant less likely to be eaten by animals that do not help it disperse. There is also evidence that capsaicin may have evolved as an
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Capsaicin deters insects in multiple ways. The first is by deterring insects from laying their eggs on the pepper due to the effects capsaicin has on these insects. Capsaicin can cause intestinal
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The primary treatment is removal of the offending substance. Plain water is ineffective at removing capsaicin. Capsaicin is soluble in alcohol, which can be used to clean contaminated items.
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Curry J, Aluru M, Mendoza M, Nevarez J, Melendrez M, O'Connell MA (1999). "Transcripts for possible capsaicinoid biosynthetic genes are differentially accumulated in pungent and non-pungent
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genus are found in diverse environments, the capsaicin found within them all exhibit similar properties that serve as defensive and adaptive features. Capsaicin evolved to preserve the
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Fujiwake H, Suzuki T, Iwai K (November 1982). "Intracellular distributions of enzymes and intermediates involved in biosynthesis of capsaicin and its analogues in Capsicum fruits".
2045:-methyltransferase. Similar studies showed high transcription levels in the placenta of chili peppers with high pungency of genes responsible for branched-chain fatty acid pathway. 1389:. In high concentrations, capsaicin will also cause a burning effect on other sensitive areas, such as skin or eyes. The degree of heat found within a food is often measured on the 8815: 5818:
partially elucidated capsaicin's chemical structure. Capsaicin was first synthesized in 1930 by Ernst Spath and Stephen F. Darling. In 1961, similar substances were isolated from
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Siemens J, Zhou S, Piskorowski R, Nikai T, Lumpkin EA, Basbaum AI, et al. (November 2006). "Spider toxins activate the capsaicin receptor to produce inflammatory pain".
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Whiting S, Derbyshire EJ, Tiwari B (February 2014). "Could capsaicinoids help to support weight management? A systematic review and meta-analysis of energy intake data".
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of further trials found weak evidence that consuming capsaicin before a meal might slightly reduce the amount of food consumed, and might drive food preference toward
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Ellis CN, Berberian B, Sulica VI, Dodd WA, Jarratt MT, Katz HI, et al. (September 1993). "A double-blind evaluation of topical capsaicin in pruritic psoriasis".
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Ingestion of high quantities of capsaicin can be deadly, particularly in people with heart problems. Even healthy young people can suffer adverse health effects like
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upon ingestion, disrupting insect metabolism and causing damage to cell membranes within the insect. This in turn disrupts the standard feeding response of insects.
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The most commonly occurring capsaicinoids are capsaicin (69%), dihydrocapsaicin (22%), nordihydrocapsaicin (7%), homocapsaicin (1%), and homodihydrocapsaicin (1%).
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to relieve pain, typically in concentrations between 0.025% and 0.1%. It may be applied in cream form for the temporary relief of minor aches and pains of
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Maurach B (1816). "Pharmaceutisch-chemische Untersuchung des spanischen Pfeffers" [Pharmaceutical-chemical investigation of Spanish peppers].
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Jensen PG, Curtis PD, Dunn JA, Austic RE, Richmond ME (September 2003). "Field evaluation of capsaicin as a rodent aversion agent for poultry feed".
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Bucholz CF (1816). "Chemische Untersuchung der trockenen reifen spanischen Pfeffers" [Chemical investigation of dry, ripe Spanish peppers].
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Levey DJ, Tewksbury JJ, Cipollini ML, Carlo TA (November 2006). "A field test of the directed deterrence hypothesis in two species of wild chili".
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activates the same pathway of pain as is activated by capsaicin, an example of a shared pathway in both plant and animal anti-mammalian defense.
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for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related
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Capsaicin is also used to deter pests, specifically mammalian pests. Targets of capsaicin repellants include voles, deer, rabbits, squirrels,
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Hőgyes E (1877). "Adatok a Capsicum annuum (paprika) alkatrészeinek élettani hatásához" [Data on the physiological effects of the pepper (
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The first pesticide product using solely capsaicin as the active ingredient was registered with the U.S. Department of Agriculture in 1962.
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Thiele R, Mueller-Seitz E, Petz M (June 2008). "Chili pepper fruits: presumed precursors of fatty acids characteristic for capsaicinoids".
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capsaicinoids. Nordihydrocapsaicin (9.1 million SHU), homocapsaicin and homodihydrocapsaicin (both 8.6 million SHU) are about half as hot.
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Gooding SM, Canter PH, Coelho HF, Boddy K, Ernst E (August 2010). "Systematic review of topical capsaicin in the treatment of pruritus".
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Antonious GF, Meyer JE, Snyder JC (2006). "Toxicity and repellency of hot pepper extracts to spider mite, Tetranychus urticae Koch".
1285:(which holds the seeds), the internal membranes and, to a lesser extent, the other fleshy parts of the fruits of plants in the genus 526:
InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+
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There is insufficient clinical evidence to determine the role of ingested capsaicin on several human disorders, including obesity,
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InChI=1/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+
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Ruiz-Lau N, Medina-Lara F, Minero-García Y, Zamudio-Moreno E, Guzmán-Antonio A, Echevarría-Machado I, et al. (1 March 2011).
14189: 13903: 8336: 8308: 3975: 3676:"Acute myocardial infarction and coronary vasospasm associated with the ingestion of cayenne pepper pills in a 25-year-old male" 2362: 1492:) for the management of this particular therapeutic indication (pain due to post-herpetic neuralgia) was approved in 2009, as a 1291:. The seeds themselves do not produce any capsaicin, although the highest concentration of capsaicin can be found in the white 7975: 5774:
Oersted HC (1820). "Sur la découverte de deux nouveaux alcalis végétaux" [On the discovery of two new plant alkalis].
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Fujiwake H, Suzuki T, Iwai K (October 1982). "Capsaicinoid formation in the protoplast from the placenta of Capsicum fruits".
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As of 2007, there was no evidence showing that weight loss is directly correlated with ingesting capsaicin. Well-designed
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Krenzelok EP, Jacobsen TD (August 1997). "Plant exposures ... a national profile of the most common plant genera".
1886: 1112: 13534: 11549: 9177: 8490: 2833: 2758:"Capsaicin: Current Understanding of Its Mechanisms and Therapy of Pain and Other Pre-Clinical and Clinical Uses" 2388: 839: 809: 5529: 14870: 13650: 12861: 12260: 11665: 10876: 9064: 8485: 8480: 7930: 4363:"Mittheilungen aus dem Institute für allgemeine Pathologie und Pharmakologie an der Universität zu Klausenburg" 4062: 1377:, it is commonly used in food products to provide added spiciness or "heat" (piquancy), usually in the form of 2088:
Biosynthesis of the capsaicinoids occurs in the glands of the pepper fruit where capsaicin synthase condenses
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Leete E, Louden MC (November 1968). "Biosynthesis of capsaicin and dihydrocapsaicin in Capsicum frutescens".
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Journal of Environmental Science and Health. Part. B, Pesticides, Food Contaminants, and Agricultural Wastes
1932: 1500:(FDA) and the European Union. A subsequent application to the FDA for Qutenza to be used as an analgesic in 14538: 14157: 13460: 11475: 9711: 9202: 9173: 8450: 8011: 6763: 6406: 2839: 2811: 2394: 1726: 1497: 952: 460: 363: 5579:"Effect of Drought Stress on Capsaicin and Antioxidant Contents in Pepper Genotypes at Reproductive Stage" 4801:"Enzymatic formation of capsaicinoid from vanillylamine and iso-type fatty acids by cell-free extracts of 14528: 14182: 12277: 10292: 10261: 9233: 5872: 5107:
Costa-Orlandi CB, Sardi JC, Pitangui NS, de Oliveira HC, Scorzoni L, Galeane MC, et al. (May 2017).
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of capsaicin in prescribed doses under research prevented subjects from complying in the study. A 2014
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When capsaicin is ingested, cold milk may be an effective way to relieve the burning sensation due to
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Tewksbury JJ, Nabhan GP (July 2001). "Seed dispersal. Directed deterrence by capsaicin in chilies".
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Tewksbury JJ, Reagan KM, Machnicki NJ, Carlo TA, Haak DC, Peñaloza AL, et al. (August 2008).
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Rollyson WD, Stover CA, Brown KC, Perry HE, Stevenson CD, McNees CA, et al. (December 2014).
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Tewksbury JJ, Reagan KM, Machnicki NJ, Carlo TA, Haak DC, Peñaloza AL, et al. (August 2008).
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The burning and painful sensations associated with capsaicin result from "defunctionalization" of
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fruits. 9. Biosynthesis of acyl moieties of capsaicin and its analogs from valine and leucine in
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Clarifying the mechanisms of capsaicin effects on skin nociceptors was part of awarding the 2021
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because of its hypersensitizing and pain-relieving properties. At the show jumping events of the
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Bennett DJ, Kirby GW (1968) Constitution and biosynthesis of capsaicin. J Chem Soc C 4:442–446
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by chili peppers, likely as deterrents against certain mammals and fungi. Pure capsaicin is a
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Sukrasno N, Yeoman MM (1993). "Phenylpropanoid metabolism during growth and development of
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Capsaicin synthase condenses vanillamine and 8-methyl-6-nonenoyl-CoA to produce capsaicin.
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Kelava L, Nemeth D, Hegyi P, Keringer P, Kovacs DK, Balasko M, et al. (April 2021).
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pathway, phenylalanine ammonia lyase (PAL), cinnamate 4-hydroxylase (C4H), caffeic acid
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Biographical information about C. F. Bucholz is also available (in German) online at:
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Caterina MJ, Schumacher MA, Tominaga M, Rosen TA, Levine JD, Julius D (October 1997).
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Suzuki T, Kawada T, Iwai K (1981). "Formation and metabolism of pungent principle of
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Claros Cuadrado JL, Pinillos EO, Tito R, Mirones CS, Gamarra Mendoza NN (May 2019).
4681: 4386: 3620: 3577: 3304: 3120: 3042: 2810:(Press release). U.S. Food and Drug Administration. 17 November 2009. Archived from 2340: 449: 14766: 14613: 14340: 14285: 14092: 13952: 13723: 13244: 13214: 13171: 13163: 12650: 12541: 11738: 11259: 11229: 11186: 11178: 10665: 10556: 9853: 9629: 9569: 9029: 8795: 8633: 8042: 7703: 7387: 7078: 6552: 5740:(1821) (this reference also contains an abstract of Bucholz's analysis of peppers). 5656:
A century of the United States pharmocopoeia 1820–1920. I. The galenical oleoresins
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Because of the burning sensation caused by capsaicin when it comes in contact with
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Some other early investigators who also extracted the active component of peppers:
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Mahmood T, Rana RM, Ahmar S, Saeed S, Gulzar A, Khan MA, et al. (June 2021).
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Stewart C, Kang BC, Liu K, Mazourek M, Moore SL, Yoo EY, et al. (June 2005).
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Nelson EK, Dawson LE (1923). "Constitution of capsaicin, the pungent principle of
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Buchheim R (1873). "Über die 'scharfen' Stoffe" [On the "hot" substance].
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American Journal of Physiology. Regulatory, Integrative and Comparative Physiology
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Valine enters the branched fatty acid pathway to produce 8-methyl-6-nonenoyl-CoA.
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Capsaicinoids are also an active ingredient in riot control and personal defense
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by the Japanese chemists S. Kosuge and Y. Inagaki, who named them capsaicinoids.
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Proceedings of the National Academy of Sciences of the United States of America
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Recent Advances in Phytochemistry 41: The Biological Activity of Phytochemicals
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In a series of articles, J. C. Thresh obtained capsaicin in almost pure form:
3518: 2934:"Topical capsaicin (high concentration) for chronic neuropathic pain in adults" 2558:
Proceedings of the National Academy of Sciences of the United States of America
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concluded there was insufficient evidence of effect. Oral capsaicin decreases
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Constant HL, Cordell GA, West DP (April 1996). "Nonivamide, a Constituent of
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Fattori V, Hohmann MS, Rossaneis AC, Pinho-Ribeiro FA, Verri WA (June 2016).
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Biographical information about Christian Friedrich Bucholz is available in:
5395: 5371:"Insecticidal Properties of Capsaicinoids and Glucosinolates Extracted from 5019: 4825: 4800: 3864:"Nobel Prize Awarded to Scientists for Research About Temperature and Touch" 2578: 2553: 2015: 14832: 14761: 14692: 14682: 14677: 14503: 14492: 14392: 14355: 14198: 14117: 14112: 14097: 14042: 14037: 14027: 13972: 13883: 13743: 13708: 13681: 13336: 13254: 13234: 13201: 13073: 12951: 12757: 12702: 12533: 12451: 12322: 12177: 12114: 12084: 11954: 11898: 11758: 11723: 11696: 11351: 11269: 11249: 11216: 11088: 10966: 10772: 10717: 10548: 10466: 10337: 10197: 10115: 10034: 10024: 9967: 9950: 9935: 9904: 9864: 9834: 9760: 9439: 9419: 9009: 8825: 8785: 8718: 8708: 8699: 8694: 8637: 8595: 8185: 7970: 7879: 7792: 7604: 7599: 7502: 7196: 7171: 6929: 6834: 6718: 6505: 6493: 6483: 6458: 6326: 6316: 6246: 6121: 6116: 6027: 5819: 5614: 5595: 5514: 5496: 5457: 5414: 5330: 5273: 5218: 5144: 5093: 5038: 4930: 4895: 4772:
Bennett DJ, Kirby GW (1968). "Constitution and biosynthesis of capsaicin".
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Bennett DJ, Kirby GW (1968). "Constitution and biosynthesis of capsaicin".
4039: 3711: 3612: 3569: 3526: 3408: 3296: 3231: 3161: 3112: 3025: 3008: 2978: 2960: 2793: 2733: 2640: 2597: 2530: 2280: 1999: 1778: 1686: 1674: 1556: 1463: 1447: 1397: 1382: 1329: 1244: 795: 785: 14487: 9263: 9187: 5877: 5254: 5185:"Understand spiciness: mechanism of TRPV1 channel activation by capsaicin" 4506: 3818: 3785:"The capsaicin receptor: a heat-activated ion channel in the pain pathway" 3692: 3443: 3077: 3034: 2443: 1058: 14746: 14553: 14422: 14382: 14305: 14295: 14235: 14062: 14057: 14052: 14032: 14022: 13947: 13828: 13645: 13640: 13635: 13412: 13385: 13229: 13136: 13126: 13101: 13081: 13006: 12991: 12981: 12961: 12738: 12679: 12609: 12580: 12506: 12317: 12207: 12137: 12130: 12125: 12096: 12074: 11993: 11976: 11843: 11660: 11655: 11650: 11427: 11400: 11244: 11151: 11141: 11116: 11096: 11021: 11006: 10996: 10976: 10753: 10694: 10624: 10595: 10521: 10332: 10169: 10159: 10135: 10120: 9962: 9927: 9922: 9811: 9806: 9674: 9638: 9615: 9554: 9503: 9493: 9443: 9363: 9049: 8977: 8961: 8829: 8801: 8684: 8628: 8571: 8557: 8245: 8240: 8180: 7909: 7894: 7889: 7843: 7782: 7709: 7689: 7668: 7629: 7492: 7457: 7325: 7242: 7222: 7131: 7040: 6971: 6963: 6924: 6849: 6799: 6794: 6693: 6629: 6557: 6401: 6386: 6377: 6311: 6296: 6291: 6281: 6276: 6271: 6221: 6201: 6196: 6191: 6160: 6155: 6111: 6096: 6065: 6044: 6022: 5074: 4785: 4728:"The Pun1 gene for pungency in pepper encodes a putative acyltransferase" 4424: 3960: 3009:"Neurogenic inflammation induced by capsaicin in patients with psoriasis" 3006: 2243: 1493: 1485: 1266: 990: 14325: 4712: 4498: 4158: 3769: 3734: 2632: 1563:, it produces pain and breathing difficulty in the affected individual. 1044: 978: 345: 14817: 14712: 14687: 14427: 14142: 14137: 14067: 14007: 13997: 13967: 13833: 13771: 13660: 13429: 13402: 13379: 13091: 13086: 12996: 12971: 12896: 12789: 12784: 12689: 12674: 12669: 12627: 12495: 12388: 12352: 12342: 12152: 12062: 11848: 11786: 11675: 11444: 11417: 11394: 11106: 11101: 11011: 10986: 10911: 10804: 10799: 10704: 10689: 10684: 10642: 10510: 10403: 10367: 10357: 10154: 10072: 9998: 9957: 9945: 9940: 9826: 9816: 9610: 9605: 9558: 9039: 8930: 8845: 8835: 8791: 8775: 8771: 8662: 8528: 8396: 8379: 8277: 8123: 8051: 8047: 7994: 7940: 7899: 7724: 7714: 7699: 7567: 7477: 7272: 7267: 7212: 7149: 7092: 7073: 7050: 7045: 7035: 7025: 6986: 6949: 6944: 6939: 6890: 6885: 6867: 6804: 6789: 6774: 6708: 6688: 6619: 6609: 6578: 6532: 6519: 6488: 6453: 6336: 6331: 6306: 6256: 6251: 6226: 6181: 6106: 5125: 4378: 4127: 4096: 2258: 2175: 1963: 1810: 1790: 1710: 1646: 1567: 1470: 1421: 1254: 1051: 681: 606: 394: 376: 316: 8433: 8291: 7862: 5287:
Li Y, Bai P, Wei L, Kang R, Chen L, Zhang M, et al. (June 2020).
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Thresh JC (1877). "Report on the active principle of Cayenne pepper".
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agents. When the spray comes in contact with skin, especially eyes or
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Capsaicin General Fact Sheet – National Pesticide Information Center
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Except where otherwise noted, data are given for materials in their
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Diepvens K, Westerterp KR, Westerterp-Plantenga MS (January 2007).
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One 2006 review concluded that capsaicin may relieve symptoms of a
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which destroy such seeds and prevent them from germinating. Thus,
1287: 1249: 1017: 424: 336: 48: 14736: 5368: 4143:"The constitution of capsaicin, the pungent principle of capsicum" 3809: 3784: 2130:
19.6 million years ago, 5.4 million years after the appearance of
1416:
effects from ingesting capsaicin. Folklore among self-described "
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Journal de physique, de chemie, d'histoire naturelle et des arts
1396:
There has long been a demand for capsaicin-spiced products like
14837: 14477: 13878: 13796: 13056: 13020: 12937: 12816: 12555: 12522: 12327: 12241: 12236: 12229: 12212: 12190: 12027: 12007: 11893: 11811: 11071: 11035: 10952: 10831: 10570: 10537: 10342: 10164: 9706: 9564: 9498: 9464: 9435: 9348: 8916: 8892: 8850: 8750: 8678: 8517: 8499: 8357: 8318: 8313: 8091: 8077: 7822: 7738: 7633: 7624: 7614: 7593: 7556: 7527: 7522: 7461: 7453: 7439: 7416: 6032: 5934: 5925: 3782: 3184:. United States Environmental Protection Agency. Archived from 2233: 2103:
Capsaicin is the most abundant capsaicinoid found in the genus
2096:
pathway with an acyl-CoA moiety produced by the branched-chain
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burning diarrhea. Eye exposure produces intense tearing, pain,
1540: 1474: 1459: 1451: 1378: 652:
210 to 220 °C (410 to 428 °F; 483 to 493 K) 0.01
296: 2911:"FDA Turns Down Capsaicin Patch for Painful Neuropathy in HIV" 827: 13209: 11224: 8920: 8656: 8652: 8609: 8523: 8292: 8159: 8136: 7776: 7653: 7536: 7467: 6266: 5973: 5938: 5648:. Vol. 1. Cincinnati, Ohio: Ohio Valley Co. p. 435. 4992: 3916:
Thresh JC (8 July 1876). "Capsaicin, the active principle in
3756:
Story GM, Crus-Orengo L (July–August 2007). "Feel the burn".
2551: 2308:. ChemSpider, Royal Society of Chemistry, Cambridge, UK. 2018 2237: 2170: 1412:. It is common for people to experience pleasurable and even 1366: 1303: 1258: 1002: 276: 242: 39: 12261:
List of phytochemicals and foods in which they are prominent
5732:(February 1821); (iii) "Spanischer oder indischer Pfeffer", 5427: 5052:
Behbehani JM, Irshad M, Shreaz S, Karched M (January 2023).
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Glinski W, Glinska-Ferenz M, Pierozynska-Dubowska M (1991).
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There are six natural capsaicinoids (table below). Although
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Journal of Physics, Chemistry, Natural History and the Arts
4116:
Zeitschrift für Untersuchung der Nahrungs- und Genussmittel
4085:
Zeitschrift für Untersuchung der Nahrungs- und Genussmittel
3883:
Almanach oder Taschenbuch für Scheidekünstler und Apotheker
2610: 1765:
The compound was first extracted in impure form in 1816 by
1754: 1302:
plants are dispersed predominantly by birds. In birds, the
1226: 1223: 1185: 627: 415: 125: 122: 84: 5481:"Why are not all chilies hot? A trade-off limits pungency" 5478: 4839: 2932:
Derry S, Rice AS, Cole P, Tan T, Moore RA (January 2017).
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Seed dispersion and deterrents against granivorous mammals
5687:. Vol. 5. London, England: T. Fellowes. p. 186. 5479:
Haak DC, McGinnis LA, Levey DJ, Tewksbury JJ (May 2012).
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Satyanarayana MN (2006). "Capsaicin and gastric ulcers".
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62 to 65 °C (144 to 149 °F; 335 to 338 K)
131: 110: 90: 72: 5803:
Contributions to Pharmaceutical and Analytical Chemistry
4647: 3090: 3055: 2834:"Drug Approval Package: Qutenza (capsaicin) NDA #022395" 2697: 2389:"Drug Approval Package: Qutenza (capsaicin) NDA #022395" 2206: 2003:
Vanillamine is a product of the phenylpropanoid pathway.
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Beiträge für die Pharmaceutische und Analytische Chemie
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Späth E, Darling SF (1930). "Synthese des Capsaicins".
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Archiv für experimentelle Pathologie und Pharmakologie
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Proceedings of the American Pharmaceutical Association
4112:"Über den wirksamen Bestandtheil des Cayennespfeffers" 3674:
Sogut O, Kaya H, Gokdemir MT, Sezen Y (January 2012).
3673: 3490:. Department of Chemistry, Frostburg State University. 3209: 3173: 3171: 2671:"A Perk of Our Evolution: Pleasure in Pain of Chilies" 14881: 5663:
The results of Bucholz's and Braconnot's analyses of
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Journal of the Agricultural Chemical Society of Japan
4209:
Journal of the Agricultural Chemical Society of Japan
4114:[On the active component of Cayenne pepper]. 2169:
capsaicin is present. Capsaicin also inhibits fungal
1469:
It is also used to reduce the symptoms of peripheral
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Terpene synthase enzymes (many), having in common a
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of the peppers reduced the seeds production by 50%.
1214: 1176: 940: 113: 75: 4437: 3887:
Almanac or Pocketbook for Analysts and Apothecaries
3168: 2473: 2471: 2252:, an ultrapotent capsaicin antagonist derived from 1217: 1179: 403: 116: 78: 13925: 4995:"Evolutionary ecology of pungency in wild chilies" 4852:. New York, New York: Springer. pp. 117–118. 4760: 4546: 4519: 4404:. Berlin, Germany: Gaertner's Verlagsbuchhandlung. 3861: 3635:"The Health Risks of Eating Extremely Spicy Foods" 2554:"Evolutionary ecology of pungency in wild chilies" 2156:of peppers against fungi infections, insects, and 2063:. Capsaicin is believed to be synthesized in the 1798:Capsaicin and dihydrocapsaicin (both 16.0 million 1575:Journal of Environmental Science and Health Part B 1516:Although capsaicin creams have been used to treat 1433: 936: 176:-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide 5659:(PhD). University of Wisconsin. pp. 111–132. 4842:"Chapter 8: Heat, Color, and Flavor Compounds in 4480: 4478: 4476: 4474: 3461:. New York, New York: McGraw-Hill. p. 1167. 3429: 1295:of the inner wall, where the seeds are attached. 14905: 4612: 3841:"The Nobel Prize in Physiology or Medicine 2021" 3755: 2931: 2479:"Chile Information – Frequently Asked Questions" 2468: 2355: 2273:; some of the world's most capsaicin-rich fruits 1281:Capsaicin is present in large quantities in the 932: 448: 14924:Transient receptor potential channel modulators 12299: 10314: 5672:The Elements of Materia Medica and Therapeutics 4944:Yang HJ, Chung KR, Kwon DY (1 September 2017). 4052: 3316: 3314: 2508: 1420:" attribute this to pain-stimulated release of 1033: 228: 9311:Iridoid glycosides (iridoids bound to a sugar) 5873:Fire and Spice: The molecular basis for flavor 4573: 4471: 4344:Orvos-természettudumányi társulatot Értesítője 3593:Critical Reviews in Food Science and Nutrition 3140:Critical Reviews in Food Science and Nutrition 3058:Journal of the American Academy of Dermatology 2424:Critical Reviews in Food Science and Nutrition 1006: 14183: 13911: 13461: 13040: 12418: 12372: 12285: 11476: 11055: 10433: 10387: 10300: 9249: 9203: 7341: 5893: 5716:Abstracts of Maurach's paper appear in: (i) 4943: 4298:Vierteljahresschrift für praktische Pharmazie 4235: 3590: 2416: 2414: 1524:involving topical capsaicin for treatment of 13054: 11069: 5286: 5109:"Fungal Biofilms and Polymicrobial Diseases" 4799:Fujiwake H, Suzuki T, Oka S, Iwai K (1980). 4771: 4694: 4414: 4171: 3903:Thresh JC (1876). "Isolation of capsaicin". 3584: 3374: 3311: 3260: 3127: 2858:"Application Number: 22-395: Summary Review" 2148:. Despite the fact that chilies within the 9217: 5907: 5840: 5641: 5062:International Journal of Molecular Sciences 4840:Guzman I, Bosland PW, O'Connell MA (2011). 4484: 3922:The Pharmaceutical Journal and Transactions 3905:The Pharmaceutical Journal and Transactions 3889:]. Vol. 37. Weimar. pp. 1–30. 3862:Santora M, Engelbrecht C (4 October 2021). 3729: 3727: 3725: 3723: 3721: 3680:International Journal of Emergency Medicine 3246:"Human Elephant Conflict and Chilli Pepper" 2941:The Cochrane Database of Systematic Reviews 2865:FDA Center for Drug Evaluation and Research 1769:(1770–1818). In 1873 German pharmacologist 1633: 14190: 14176: 13918: 13904: 13468: 13454: 13047: 13033: 12425: 12411: 12379: 12365: 12292: 12278: 11483: 11469: 11062: 11048: 10440: 10426: 10394: 10380: 10307: 10293: 9256: 9242: 9210: 9196: 7355: 7348: 7334: 5900: 5886: 5681:Rose HJ (1857). Rose HJ, Wright T (eds.). 5234:"Regulation of Ergosterol Biosynthesis in 4911:Journal of Agricultural and Food Chemistry 4876:Journal of Agricultural and Food Chemistry 4348:ulletin of the Medical Science Association 2751: 2749: 2747: 2745: 2743: 2411: 2182: 1520:for reduction of itching, a review of six 1247:, which are plants belonging to the genus 994: 501: 366: 324: 27:Pungent chemical compound in chili peppers 13943:β-Hydroxybutyric acid (β-hydroxybutyrate) 5811:He called it "capsicin", after the genus 5747: 5638:History of early research on capsaicin: 5604: 5594: 5545: 5504: 5404: 5394: 5320: 5263: 5253: 5231: 5208: 5182: 5176: 5134: 5124: 5083: 5073: 5028: 5018: 4961: 4824: 4743: 4399: 4257: 4220: 4083:[On our knowledge of capsaicin]. 4029: 3808: 3701: 3691: 3456: 3398: 3151: 3024: 2968: 2783: 2773: 2723: 2587: 2577: 2335: 2333: 2331: 2329: 2327: 2325: 2323: 2070:of chili peppers and depends on the gene 1656: 1645:in milk, and the water of milk acts as a 1550: 468: 12386: 10401: 4487:Journal of the American Chemical Society 4318: 4302:Quarterly Journal for Practical Pharmacy 4295: 4272: 4147:Journal of the American Chemical Society 4006:"John Clough Thresh, M.D., D.Sc., D.P.H" 3718: 2163: 2014: 2006: 1998: 1990: 1361: 12432: 10447: 5795: 5773: 5708:Berlinisches Jahrbuch für die Pharmacie 5705: 5668: 4199:Kosuge S, Inagaki Y, Okumura H (1961). 3930:[Note: This article is summarized in: 3880: 3380: 2740: 2048: 1701:after ingestion of capsaicin capsules. 1605: 497: 344: 14: 14906: 5652: 4360: 4337: 4319:Buchheim R (1873). "Fructus Capsici". 4296:Buchheim R (1872). "Fructus Capsici". 4140: 3986: 3973: 3915: 3902: 3481: 3355:. sciencelab.com. 2007. Archived from 3353:"Capsaicin Material Safety Data Sheet" 3347: 3345: 3343: 2693: 2691: 2668: 2664: 2662: 2660: 2658: 2320: 1704: 818: 357: 14171: 13899: 13449: 13028: 12406: 12360: 12273: 11464: 11043: 10421: 10375: 10288: 9237: 9191: 7528:CS gas (2-chlorobenzal malononitrile) 7329: 5881: 5684:A New General Biographical Dictionary 4813:Agricultural and Biological Chemistry 4549:Agricultural and Biological Chemistry 4522:Agricultural and Biological Chemistry 4109: 4078: 2207:Adaptation to varying moisture levels 1751:Nobel Prize in Physiology or Medicine 848: 529:Key: YKPUWZUDDOIDPM-SOFGYWHQSA-N 304: 284: 14866: 5680: 4053:King J, Felter HW, Lloys JU (1905). 3933:"Capsaicin, the active principle in 3450: 3093:International Journal of Dermatology 2908: 2604: 1826: 1741:of the neuron stimulates it to send 1649:, allowing the capsaicin to form an 1584: 799: 789: 560:O=C(NCc1cc(OC)c(O)cc1)CCCC/C=C/C(C)C 9100:N-(p-Amylcinnamoyl)anthranilic acid 8216:N-(p-Amylcinnamoyl)anthranilic acid 7956:N-(p-Amylcinnamoyl)anthranilic acid 5843:Capsaicin as a Therapeutic Molecule 3459:Goldfrank's Toxicologic Emergencies 3457:Goldfrank LR, ed. (23 March 2007). 3387:International Journal of Toxicology 3340: 2688: 2655: 2458:"What Made Chili Peppers So Spicy?" 2450: 1665:had not been performed because the 1600: 1589:Capsaicin is a banned substance in 1276: 539:Key: YKPUWZUDDOIDPM-SOFGYWHQBQ 439: 423: 24: 13475: 11490: 10235:terpene synthase N terminal domain 5833: 4635:10.1093/oxfordjournals.pcp.a076142 4402:Pharmakognosie des Pflanzenreiches 1757:causing sensitivity to capsaicin. 1713:nerve fibers by causing a topical 1029: 25: 14935: 14197: 6992:Tetrahydrocannabinol (dronabinol) 5861: 5794:Ernst Witting, German apothecary 4222:10.1271/nogeikagaku1924.35.10_923 4057:. Eclectic Medical Publications. 4003:Obituary notice of J. C. Thresh: 3322:"Olympic horses fail drugs tests" 2059:produce capsaicinoids, which are 1689:rather than being a cause of it. 1273:(i.e., spicy) crystalline solid. 14891: 14865: 14856: 14855: 14636: 5755:Annales de Chimie et de Physique 5485:Proceedings. Biological Sciences 5345:"Capsaicin Technical Fact Sheet" 4745:10.1111/j.1365-313X.2005.02410.x 3105:10.1111/j.1365-4632.2010.04537.x 2053:Plants exclusively of the genus 1976: 1954: 1931: 1908: 1885: 1862: 1811:vanillylamide of n-nonanoic acid 1784: 1725:on nociceptor fibers called the 1717:in the skin. As a member of the 1462:, often in compounds with other 1261:(capsaicinoids) are produced as 1204: 1166: 1090: 902: 897: 892: 887: 593: 587: 103: 65: 47: 38: 13953:Acetoacetic acid (acetoacetate) 13535:p-Hydroxybenzoic acid glucoside 11550:p-Hydroxybenzoic acid glucoside 5632: 5570: 5521: 5472: 5421: 5362: 5337: 5280: 5225: 5151: 5100: 5045: 4986: 4937: 4902: 4866: 4833: 4792: 4719: 4688: 4641: 4606: 4567: 4540: 4513: 4462: 4431: 4408: 4393: 4354: 4331: 4312: 4289: 4266: 4229: 4192: 4165: 4134: 4103: 4072: 4046: 3997: 3893: 3874: 3855: 3833: 3776: 3749: 3667: 3647: 3627: 3541: 3494: 3475: 3432:Veterinary and Human Toxicology 3423: 3238: 3203: 3084: 3049: 3000: 2925: 2902: 2873: 2826: 2800: 2174:proliferate. Additionally, the 2081:, and which encodes a putative 1986: 1680: 1434:Research and pharmaceutical use 1332:-containing venom of a certain 1086:(at 25 °C , 100 kPa). 13927:Histone deacetylase inhibitors 13704:α-Cyano-4-hydroxycinnamic acid 13651:Phloroglucinol carboxylic acid 12862:List of phytochemicals in food 11719:α-Cyano-4-hydroxycinnamic acid 11666:Phloroglucinol carboxylic acid 10877:List of phytochemicals in food 6760:Aspirin (acetylsalicylic acid) 5693:Allgemeine Deutsche Biographie 5183:Yang F, Zheng J (March 2017). 4561:10.1080/00021369.1982.10865477 4534:10.1080/00021369.1982.10865495 4259:10.1271/nogeikagaku1924.36.251 4081:"Zur Kenntniss des Capsaïcins" 4055:A King's American Dispensatory 4016:(3726): 1057–1058. June 1932. 2953:10.1002/14651858.CD007393.pub4 2913:. Medscape Medical News, WebMD 2669:Gorman J (20 September 2010). 2545: 2381: 2298: 2279:the active flavor chemical in 1737:when activated. The resulting 596: 581: 13: 1: 14158:Receptor/signaling modulators 9174:Receptor/signaling modulators 7523:CR gas (dibenzoxazepine; DBO) 5718:Repertorium für die Pharmacie 5232:Jordá T, Puig S (July 2020). 4674:10.1016/s0168-9452(99)00118-1 3482:Senese F (23 February 2018). 3153:10.1080/10408398.2021.1910138 2716:10.1016/j.jconrel.2014.09.027 2704:Journal of Controlled Release 2291: 1721:family, capsaicin binds to a 9712:Geranylgeranyl pyrophosphate 5726:Allgemeine Literatur-Zeitung 5645:King's American Dispensatory 5642:Felter HW, Lloyd JU (1898). 4600:10.1016/0031-9422(93)85217-f 4236:Kosuge S, Inagaki Y (1962). 3179:"R.E.D. Facts for Capsaicin" 3070:10.1016/0190-9622(93)70208-B 2840:Food and Drug Administration 2395:Food and Drug Administration 2232:flavor chemical in uncooked 2117: 2023: 1727:vanilloid receptor subtype 1 1618:in mice is 47.2 mg/kg. 1573:An article published in the 1498:Food and Drug Administration 1243:) is an active component of 7: 14083:Sodium oxybate (GHB sodium) 13187:Pyrocatecollic type tannins 11202:Pyrocatecollic type tannins 10262:Dimethylallyl pyrophosphate 8802:Paracetamol (acetaminophen) 7710:Paracetamol (acetaminophen) 7580:Farnesyl thiosalicylic acid 7408:15-Deoxy-Δ-prostaglandin J2 6402:Paracetamol (acetaminophen) 5159:"How fungi are constructed" 4623:Plant & Cell Physiology 3970:(1876), pages 250 and 543; 3562:10.1016/j.appet.2013.11.005 2219: 1777:and increased secretion of 1767:Christian Friedrich Bucholz 1454:and joints associated with 1319:agent. The fungal pathogen 10: 14940: 5313:10.1038/s41598-020-66900-2 3737:. DrugBank. 4 January 2023 3519:10.1152/ajpregu.00832.2005 3013:Acta Dermato-Venereologica 1788: 1760: 1355: 14851: 14800: 14726: 14645: 14634: 14592: 14584:Trinidad Scorpion Butch T 14466: 14436: 14214: 14205: 14151: 14123:Valproic acid (valproate) 13933: 13868: 13842: 13809: 13757: 13694: 13669: 13606: 13573:3,5-Dihydroxybenzoic acid 13568:2,6-Dihydroxybenzoic acid 13563:2,4-Dihydroxybenzoic acid 13557:2,3-Dihydroxybenzoic acid 13547: 13527: 13501: 13483: 13440: 13421: 13361: 13306: 13281: 13200: 13162: 13135: 13072: 13063: 13019: 13005: 12970: 12936: 12922: 12909: 12852: 12830: 12807: 12798: 12775: 12748: 12725: 12716: 12688: 12660: 12637: 12608: 12579: 12563: 12554: 12532: 12505: 12482: 12459: 12450: 12441: 12395: 12351: 12308: 12252: 12176: 12113: 12095: 12053: 11914: 11883: 11857: 11824: 11772: 11709: 11684: 11621: 11588:3,5-Dihydroxybenzoic acid 11583:2,6-Dihydroxybenzoic acid 11578:2,4-Dihydroxybenzoic acid 11572:2,3-Dihydroxybenzoic acid 11562: 11542: 11516: 11498: 11455: 11436: 11376: 11321: 11296: 11215: 11177: 11150: 11087: 11078: 11034: 11020: 10985: 10951: 10937: 10924: 10867: 10845: 10822: 10813: 10790: 10763: 10740: 10731: 10703: 10675: 10652: 10623: 10594: 10578: 10569: 10547: 10520: 10497: 10474: 10465: 10456: 10410: 10366: 10323: 10277: 10256:Isopentenyl pyrophosphate 10248: 10226: 10210:Norisoprenoids (modified) 10209: 10182: 10134: 10081: 10066: 10049: 9986: 9913: 9903: 9886: 9825: 9799: 9769: 9744: 9723: 9699: 9689: 9628: 9583: 9532: 9486: 9477: 9428: 9402: 9381: 9362: 9324: 9281: 9226: 9167: 8970: 8443: 8432: 8412: 8389: 8378: 8350: 8301: 8290: 8168: 8004: 7993: 7918: 7872: 7861: 7801: 7380: 7369: 7286: 7205: 7162: 7140: 7103:Tricyclic antidepressants 7059: 7011: 7000: 6962: 6917: 6866: 6750: 6717: 6666: 6602: 6566: 6476: 6467: 6376: 6174: 5992: 5933: 5924: 5734:System der Materia medica 5547:10.21273/HORTSCI.46.3.487 5450:10.1007/s00442-006-0496-y 5201:10.1007/s13238-016-0353-7 4963:10.1016/j.jef.2017.08.010 4242:Nippon Nogeikagaku Kaishi 4205:Nippon Nogeikagaku Kaishi 4022:10.1136/bmj.1.3726.1057-c 3605:10.1080/1040-830491379236 3400:10.1080/10915810601163939 2886:European Medicines Agency 2775:10.3390/molecules21070844 2436:10.1080/10408399109527536 2236:, and to a lesser extent 1715:hypersensitivity reaction 1141: 1137:(pure capsaicin is toxic) 1131: 1126: 1080: 868: 863: 772: 755: 622:Crystalline white powder 568: 548: 513: 212: 165: 145: 55: 46: 37: 14579:Trinidad Moruga scorpion 13494:Monohydroxybenzoic acids 13150:1,3,6-Trigalloyl glucose 12043:Syn-propanethial-S-oxide 11965:Phenethyl Isothiocyanate 11509:Monohydroxybenzoic acids 11165:1,3,6-Trigalloyl glucose 10249:Activated isoprene forms 10050:Sesquarterpenes/oids (7) 9299:Monocyclic (single ring) 7787:Umbellularia californica 6437:+propyphenazone/caffeine 5770:Johann Georg Forchhammer 5625: 5236:Saccharomyces cerevisiae 4186:10.1002/cber.19300630331 3488:General Chemistry Online 3289:10.1080/0360123060096419 2363:"Qutenza- capsaicin kit" 2271:Trinidad Moruga Scorpion 1692: 1634:Treatment after exposure 1458:, backache, strains and 1438:Capsaicin is used as an 953:Precautionary statements 13973:Butyric acid (butyrate) 13608:Trihydroxybenzoic acids 12872:O-methylated flavonoids 12867:C-methylated flavonoids 12122:Saturated cyclic acids 11623:Trihydroxybenzoic acids 10887:O-methylated flavonoids 10882:C-methylated flavonoids 9872:Secodehydroabietic acid 8757:N-Arachidonoyl dopamine 8539:Andrographis paniculata 5841:Abdel-Salam OM (2014). 5396:10.3390/insects10050132 5020:10.1073/pnas.0802691105 4950:Journal of Ethnic Foods 4826:10.1271/bbb1961.44.2907 4010:British Medical Journal 3212:Pest Management Science 2909:Hitt E (9 March 2012). 2579:10.1073/pnas.0802691105 2183:Insecticidal properties 2111:phenylpropanoid pathway 2074:, which resides at the 1545:cardiovascular diseases 1351: 1346: 159:--8-methylnon-6-enamide 14813:Chile Pepper Institute 13549:Dihydroxybenzoic acids 12912:Flavonoid biosynthesis 12750:3-hydroxyanthocyanidin 11564:Dihydroxybenzoic acids 10927:Flavonoid biosynthesis 10765:3-hydroxyanthocyanidin 9667:Farnesyl pyrophosphate 9178:Ion channel modulators 8907:Tetrahydrocannabivarin 8402:Tripterygium wilfordii 7768:Tetrahydrocannabiorcol 6287:Pethidine (meperidine) 5596:10.3390/plants10071286 5497:10.1098/rspb.2011.2091 4361:Högyes A (June 1878). 3968:Year Book of Pharmacy… 3843:. Nobel Prize Outreach 3026:10.2340/00015555715154 2246:, capsaicin antagonist 2020: 2012: 2004: 1996: 1657:Weight loss and regain 1551:Pepper spray and pests 1370: 1339:Psalmopoeus cambridgei 1162:-vanillyl-6-nonenamide 1040: 195:-vanillylnon-6-enamide 14529:Hainan yellow lantern 14088:Sodium phenylbutyrate 13938:3,3'-Diindolylmethane 13696:Hydroxycinnamic acids 13578:Ethyl protocatechuate 13514:4-Hydroxybenzoic acid 13509:3-Hydroxybenzoic acid 13283:Flavono-ellagitannins 13274:Phlorofucofuroeckol B 13250:Phlorofucofuroeckol A 13182:Catechol-type tannins 13177:Polyflavonoid tannins 12727:3-deoxyanthocyanidins 12018:3,3'-Diindolylmethane 11946:Aglycone derivatives 11711:Hydroxycinnamic acids 11593:Ethyl protocatechuate 11529:4-Hydroxybenzoic acid 11524:3-Hydroxybenzoic acid 11298:Flavono-ellagitannins 11289:Phlorofucofuroeckol B 11265:Phlorofucofuroeckol A 11197:Catechol-type tannins 11192:Polyflavonoid tannins 10742:3-deoxyanthocyanidins 9869:Sandaracopimaric acid 9514:Geranyl pyrophosphate 8735:Lysophosphatidic acid 6908:+paracetamol/caffeine 6886:Metamizole (dipyrone) 6820:Morpholine salicylate 6764:+paracetamol/caffeine 5255:10.3390/genes11070795 4400:Flückiger FA (1891). 4350:] (in Hungarian). 4248:] (in Japanese). 4211:] (in Japanese). 3989:Year Book of Pharmacy 3980:Year Book of Pharmacy 3693:10.1186/1865-1380-5-5 2286:List of capsaicinoids 2164:Antifungal properties 2018: 2010: 2002: 1994: 1699:myocardial infarction 1365: 1263:secondary metabolites 1039: 14823:Hot pepper challenge 14133:Valproate semisodium 13759:Aromatic amino acids 13670:Other phenolic acids 13065:Hydrolysable tannins 12957:Secoisolariciresinol 12033:Allyl isothiocyanate 11960:Allyl isothiocyanate 11774:Aromatic amino acids 11685:Other phenolic acids 11080:Hydrolysable tannins 10972:Secoisolariciresinol 10059:Tetraprenylcurcumene 9540:Grapefruit mercaptan 9115:Pregnenolone sulfate 8936:Euphorbia resinifera 8878:Euphorbia resinifera 8807:Phenylacetylrinvanil 8767:N-Oleoylethanolamide 8715:Homodihydrocapsaicin 8103:Pregnenolone sulfate 7966:Pregnenolone sulfate 7773:Thiopropanal S-oxide 7758:Tetrahydrocannabinol 7446:Allyl isothiocyanate 7031:Gabapentin enacarbil 6825:Potassium salicylate 6815:Magnesium salicylate 6810:Imidazole salicylate 6637:Indometacin farnesil 6033:Diamorphine (heroin) 6000:Acetyldihydrocodeine 5772:, Danish geologist 5377:Tropaeolum tuberosum 5075:10.3390/ijms24021046 4848:. In Gang DR (ed.). 4786:10.1039/j39680000442 4425:10.1039/j39680000442 4275:Archiv der Heilkunde 3961:10.1039/an876010148b 3947:(8): 148–149. 1876. 3362:on 29 September 2007 2049:Biosynthetic pathway 1941:Homodihydrocapsaicin 1733:to pass through the 1606:Acute health effects 1595:2008 Summer Olympics 1269:, colorless, highly 1022:(fire diamond) 699:Slightly soluble in 689:Soluble in alcohol, 147:Preferred IUPAC name 14828:Hunan hand syndrome 14595:Capsicum frutescens 13792:5-hydroxytryptophan 13598:Protocatechuic acid 13307:Other Miscellaneous 12310:Natural monophenols 11807:5-hydroxytryptophan 11613:Protocatechuic acid 11322:Other Miscellaneous 10325:Natural monophenols 9842:Dehydroabietic acid 9308:(cyclopentane ring) 9020:Cannabigerolic acid 8782:Nordihydrocapsaicin 8743:(acidic conditions) 6780:Carbasalate calcium 5805:] (in French). 5782:] (in French). 5491:(1735): 2012–2017. 5442:2006Oecol.150...61L 5305:2020NatSR..10.9963L 5011:2008PNAS..10511808T 5005:(33): 11808–11811. 4713:10.1021/ja01662a023 4666:1999PlnSc.148...47C 4592:1993PChem..32..839S 4576:Capsicum frutescens 4499:10.1021/ja01026a049 4304:] (in German). 4279:Archive of Medicine 4159:10.1021/ja02228a011 3976:"Note on Capsaicin" 3953:1876Ana.....1..148. 3801:1997Natur.389..816C 3770:10.1511/2007.66.326 3281:2006JESHB..41.1383A 2988:on 15 February 2021 2890:. 17 September 2018 2867:. 13 November 2009. 2814:on 23 November 2015 2633:10.1038/nature05285 2625:2006Natur.444..208S 2570:2008PNAS..10511808T 2564:(33): 11808–11811. 2263:Bhut Jolokia Pepper 2250:Iodoresiniferatoxin 2142:, across the genus 1895:Nordihydrocapsaicin 1845:Chemical structure 1705:Mechanism of action 1532:levels moderately. 1511:diabetic neuropathy 663:Solubility in water 614: g·mol 266:Beilstein Reference 34: 14673:Chili pepper water 14668:Chili pepper paste 13879:Phenolic compounds 13122:Tellimagrandin IIs 12302:phenolic compounds 11894:Phenolic compounds 11137:Tellimagrandin IIs 10317:phenolic compounds 10279:Phenolic compounds 9302:Bicyclic (2 rings) 8983:Vernonia tweediana 8562:African blue basil 8534:Bisandrographolide 8120:Steviol glycosides 8073:Hydroxycitronellal 7819:Dehydroligustilide 7639:Angelica acutiloba 7553:Dehydroligustilide 7313:Never to phase III 7218:Analgesic adjuvant 7119:1.7/1.8-selective: 6785:Choline salicylate 6212:Dextropropoxyphene 5728:, vol. 4, no. 18, 5669:Pereira J (1854). 5653:Du Mez AG (1917). 5293:Scientific Reports 5189:Protein & Cell 5163:website.nbm-mnb.ca 5126:10.3390/jof3020022 4809:cv. Karayatsubusa" 4379:10.1007/BF02125956 4141:Nelson EK (1919). 4128:10.1007/bf02529197 4097:10.1007/bf02529190 3974:Thresh JC (1877). 3868:The New York Times 3758:American Scientist 3393:(Suppl 1): 3–106. 3381:Johnson W (2007). 3191:on 24 October 2012 2462:Talk of the Nation 2098:fatty acid pathway 2039:fatty acid pathway 2021: 2013: 2005: 1997: 1823:Capsaicinoid name 1371: 1113:Infobox references 1041: 32: 14879: 14878: 14782:Sweet chili sauce 14632: 14631: 14514:Ellachipur Sanman 14469:Capsicum chinense 14439:Capsicum baccatum 14165: 14164: 14143:Vorinostat (SAHA) 14128:Valproate pivoxil 14013:Indole-3-carbinol 13993:Diallyl disulfide 13893: 13892: 13805: 13804: 13690: 13689: 13588:Homogentisic acid 13559:(Hypogallic acid) 13543: 13542: 13436: 13435: 13357: 13356: 13324:Synthetic tannins 13286:(complex tannins) 13172:Proanthocyanidins 13164:Condensed tannins 13158: 13157: 13145:Digalloyl glucose 13055:Types of natural 12918: 12917: 12905: 12904: 12848: 12847: 12821:Isoliquiritigenin 12771: 12770: 12712: 12711: 12550: 12549: 12267: 12266: 12013:Indole-3-carbinol 11999:Diallyl disulfide 11908: 11907: 11820: 11819: 11705: 11704: 11603:Homogentisic acid 11574:(Hypogallic acid) 11558: 11557: 11451: 11450: 11372: 11371: 11339:Synthetic tannins 11301:(complex tannins) 11187:Proanthocyanidins 11179:Condensed tannins 11173: 11172: 11160:Digalloyl glucose 11070:Types of natural 10933: 10932: 10920: 10919: 10863: 10862: 10836:Isoliquiritigenin 10786: 10785: 10727: 10726: 10565: 10564: 10271: 10270: 10219:7,8-dihydroionone 10178: 10177: 10045: 10044: 9882: 9881: 9850:Lambertianic acid 9624: 9623: 9473: 9472: 9288:Acyclic (linear, 9185: 9184: 9163: 9162: 9095:Meclofenamic acid 8901:melegueta peppers 8772:Nonivamide (PAVA) 8508:melegueta peppers 8428: 8427: 8374: 8373: 8286: 8285: 8206:Meclofenamic acid 8129:Stevia rebaudiana 7989: 7988: 7951:Meclofenamic acid 7857: 7856: 7747:melegueta peppers 7720:Phenacyl chloride 7675:N-Methylmaleimide 7665:Methyl salicylate 7610:Hydrogen peroxide 7563:Diallyl disulfide 7425:melegueta peppers 7323: 7322: 7158: 7157: 7142:Potassium openers 7079:Local anesthetics 7021:Alcohol (ethanol) 6958: 6957: 6857:methyl salicylate 6845:Sodium salicylate 6732:Meclofenamic acid 6407:+aspirin/caffeine 6372: 6371: 5852:978-3-0348-0827-9 5746:, French chemist 5373:Capsicum chinense 4923:10.1021/jf073420h 4917:(11): 4219–4224. 4888:10.1021/jf050469j 4882:(23): 9172–9181. 4819:(12): 2907–2912. 4732:The Plant Journal 4555:(10): 2591–2592. 4528:(11): 2685–2689. 4493:(24): 6837–6841. 4456:10.1021/np9600816 3795:(6653): 816–824. 3468:978-0-07-144310-4 3248:. Elephant Pepper 3146:(25): 7025–7035. 2619:(7116): 208–212. 2517:(6845): 403–404. 2464:. 15 August 2008. 2369:. 10 January 2023 2259:Naga Viper pepper 2140:natural selection 2126:genus split from 1984: 1983: 1663:clinical research 1591:equestrian sports 1585:Equestrian sports 1509:-neuropathy, and 1496:by both the U.S. 1444:topical ointments 1313:natural selection 1253:. It is a potent 1151: 1150: 1121:Chemical compound 1119: 1118: 1072:Safety data sheet 927:Hazard statements 852: 821: 763:Crystal structure 482:CompTox Dashboard 254:Interactive image 16:(Redirected from 14931: 14896: 14895: 14894: 14887: 14869: 14868: 14859: 14858: 14767:Pickapeppa Sauce 14640: 14604:African Birdseye 14212: 14211: 14192: 14185: 14178: 14169: 14168: 14093:Sodium valproate 13920: 13913: 13906: 13897: 13896: 13860:Alkylresorcinols 13724:Chlorogenic acid 13499: 13498: 13490: 13489: 13470: 13463: 13456: 13447: 13446: 13397:Phenylpropanoids 13369:Diarylheptanoids 13245:Fucophlorethol A 13070: 13069: 13049: 13042: 13035: 13026: 13025: 12887:Prenylflavonoids 12882:Pyranoflavonoids 12877:Furanoflavonoids 12805: 12804: 12723: 12722: 12651:Leucodelphinidin 12639:Flavan-3,4-diols 12561: 12560: 12542:Dalbergichromene 12457: 12456: 12448: 12447: 12427: 12420: 12413: 12404: 12403: 12381: 12374: 12367: 12358: 12357: 12294: 12287: 12280: 12271: 12270: 11875:Alkylresorcinols 11739:Chlorogenic acid 11514: 11513: 11505: 11504: 11485: 11478: 11471: 11462: 11461: 11412:Phenylpropanoids 11384:Diarylheptanoids 11260:Fucophlorethol A 11085: 11084: 11064: 11057: 11050: 11041: 11040: 10902:Prenylflavonoids 10897:Pyranoflavonoids 10892:Furanoflavonoids 10820: 10819: 10738: 10737: 10666:Leucodelphinidin 10654:Flavan-3,4-diols 10576: 10575: 10557:Dalbergichromene 10472: 10471: 10463: 10462: 10442: 10435: 10428: 10419: 10418: 10396: 10389: 10382: 10373: 10372: 10309: 10302: 10295: 10286: 10285: 10079: 10078: 9911: 9910: 9888:Sesterterpenoids 9854:Levopimaric acid 9716:Geranyl-linalool 9697: 9696: 9630:Sesquiterpenoids 9570:Perillyl alcohol 9484: 9483: 9379: 9378: 9258: 9251: 9244: 9235: 9234: 9212: 9205: 9198: 9189: 9188: 9030:Cannabigerovarin 8762:N-Oleoyldopamine 8668:Euodia ruticarpa 8634:Dihydrocapsaicin 8441: 8440: 8437: 8387: 8386: 8383: 8299: 8298: 8295: 8043:Cooling Agent 10 8002: 8001: 7998: 7870: 7869: 7866: 7388:4-Hydroxynonenal 7378: 7377: 7374: 7359: 7350: 7343: 7336: 7327: 7326: 7013:Calcium blockers 7009: 7008: 6905: 6854: 6680: 6668:COX-2 inhibitors 6634: 6553:Tiaprofenic acid 6524: 6511: 6503: 6474: 6473: 6351: 6131: 6070: 6042: 6014: 5931: 5930: 5902: 5895: 5888: 5879: 5878: 5856: 5827: 5810: 5791: 5766: 5715: 5688: 5676: 5660: 5649: 5636: 5619: 5618: 5608: 5598: 5574: 5568: 5567: 5549: 5525: 5519: 5518: 5508: 5476: 5470: 5469: 5425: 5419: 5418: 5408: 5398: 5366: 5360: 5359: 5357: 5355: 5341: 5335: 5334: 5324: 5284: 5278: 5277: 5267: 5257: 5229: 5223: 5222: 5212: 5180: 5174: 5173: 5171: 5169: 5155: 5149: 5148: 5138: 5128: 5113:Journal of Fungi 5104: 5098: 5097: 5087: 5077: 5056:Candida albicans 5049: 5043: 5042: 5032: 5022: 4990: 4984: 4983: 4965: 4941: 4935: 4934: 4906: 4900: 4899: 4870: 4864: 4863: 4837: 4831: 4830: 4828: 4796: 4790: 4789: 4769: 4758: 4757: 4747: 4723: 4717: 4716: 4707:(9): 2179–2181. 4692: 4686: 4685: 4645: 4639: 4638: 4610: 4604: 4603: 4571: 4565: 4564: 4544: 4538: 4537: 4517: 4511: 4510: 4482: 4469: 4466: 4460: 4459: 4444:Natural Products 4435: 4429: 4428: 4412: 4406: 4405: 4397: 4391: 4390: 4373:(1–2): 117–130. 4358: 4352: 4351: 4335: 4329: 4328: 4316: 4310: 4309: 4293: 4287: 4286: 4270: 4264: 4263: 4261: 4233: 4227: 4226: 4224: 4196: 4190: 4189: 4169: 4163: 4162: 4153:(7): 1115–1121. 4138: 4132: 4131: 4110:Micko K (1899). 4107: 4101: 4100: 4079:Micko K (1898). 4076: 4070: 4068: 4050: 4044: 4043: 4033: 4001: 3995: 3992: 3983: 3964: 3929: 3912: 3897: 3891: 3890: 3878: 3872: 3871: 3859: 3853: 3852: 3850: 3848: 3837: 3831: 3830: 3812: 3780: 3774: 3773: 3753: 3747: 3746: 3744: 3742: 3731: 3716: 3715: 3705: 3695: 3671: 3665: 3664: 3651: 3645: 3644: 3643:. 12 March 2023. 3640:Cleveland Clinic 3631: 3625: 3624: 3588: 3582: 3581: 3545: 3539: 3538: 3498: 3492: 3491: 3484:"Fire and Spice" 3479: 3473: 3472: 3454: 3448: 3447: 3427: 3421: 3420: 3402: 3378: 3372: 3371: 3369: 3367: 3361: 3349: 3338: 3337: 3335: 3333: 3328:. 21 August 2008 3318: 3309: 3308: 3275:(8): 1383–1391. 3264: 3258: 3257: 3255: 3253: 3242: 3236: 3235: 3218:(9): 1007–1015. 3207: 3201: 3200: 3198: 3196: 3190: 3183: 3175: 3166: 3165: 3155: 3131: 3125: 3124: 3088: 3082: 3081: 3053: 3047: 3046: 3028: 3004: 2998: 2997: 2995: 2993: 2987: 2981:. Archived from 2972: 2938: 2929: 2923: 2922: 2920: 2918: 2906: 2900: 2899: 2897: 2895: 2877: 2871: 2868: 2862: 2853: 2851: 2849: 2830: 2824: 2823: 2821: 2819: 2804: 2798: 2797: 2787: 2777: 2753: 2738: 2737: 2727: 2695: 2686: 2685: 2683: 2681: 2666: 2653: 2652: 2608: 2602: 2601: 2591: 2581: 2549: 2543: 2542: 2523:10.1038/35086653 2506: 2495: 2494: 2492: 2490: 2475: 2466: 2465: 2454: 2448: 2447: 2418: 2409: 2408: 2406: 2404: 2399:. 3 October 2013 2385: 2379: 2378: 2376: 2374: 2359: 2353: 2352: 2350: 2348: 2337: 2318: 2317: 2315: 2313: 2302: 1980: 1958: 1935: 1912: 1889: 1872:Dihydrocapsaicin 1866: 1828: 1820: 1819: 1775:mucous membranes 1601:Irritant effects 1561:mucous membranes 1375:mucous membranes 1283:placental tissue 1277:Natural function 1242: 1241: 1238: 1237: 1234: 1231: 1228: 1225: 1222: 1219: 1216: 1213: 1210: 1201: 1200: 1197: 1196: 1193: 1190: 1187: 1184: 1181: 1178: 1175: 1172: 1124: 1123: 1103: 1097: 1094: 1093: 1061: 1054: 1047: 1032: 1012: 1008: 1004: 1000: 996: 992: 988: 984: 980: 976: 972: 968: 964: 960: 946: 942: 938: 934: 906: 901: 896: 891: 850: 847: 831: 820: 817: 803: 793: 736: 732: 730: 675: 671: 655: 613: 598: 595: 589: 583: 576:Chemical formula 506: 505: 490: 488: 472: 452: 441: 427: 407: 378: 370: 359: 348: 328: 308: 288: 256: 232: 141: 140: 137: 136: 133: 130: 127: 124: 121: 118: 115: 112: 109: 100: 99: 96: 95: 92: 89: 86: 83: 80: 77: 74: 71: 51: 42: 35: 31: 21: 14939: 14938: 14934: 14933: 14932: 14930: 14929: 14928: 14919:CYP3A4 inducers 14904: 14903: 14902: 14892: 14890: 14882: 14880: 14875: 14847: 14796: 14722: 14658:Chili con carne 14641: 14628: 14588: 14544:Madame Jeanette 14509:Dragon's Breath 14499:Carolina Reaper 14462: 14432: 14366:Santa Fe Grande 14217:Capsicum annuum 14201: 14196: 14166: 14161: 14147: 14078:Sodium butyrate 13958:Allyl mercaptan 13929: 13924: 13894: 13889: 13864: 13838: 13811:Phenylethanoids 13801: 13753: 13729:Diferulic acids 13686: 13665: 13602: 13593:Orsellinic acid 13539: 13523: 13479: 13474: 13432: 13417: 13391:Naphthoquinones 13353: 13302: 13293:Epicutissimin A 13285: 13277: 13196: 13154: 13131: 13059: 13053: 13015: 13001: 12974: 12966: 12944: 12940: 12932: 12914: 12901: 12844: 12832:Dihydrochalcone 12826: 12794: 12767: 12744: 12708: 12684: 12656: 12633: 12612: 12604: 12583: 12575: 12546: 12528: 12501: 12478: 12437: 12431: 12399: 12391: 12385: 12347: 12304: 12298: 12268: 12263: 12248: 12203:Polysaccharides 12186:Monosaccharides 12172: 12109: 12091: 12049: 11950:Isothiocyanates 11935:Gluconasturtiin 11925:isothiocyanates 11910: 11909: 11904: 11879: 11853: 11826:Phenylethanoids 11816: 11768: 11744:Diferulic acids 11701: 11680: 11617: 11608:Orsellinic acid 11554: 11538: 11494: 11489: 11447: 11432: 11406:Naphthoquinones 11368: 11317: 11308:Epicutissimin A 11300: 11292: 11211: 11169: 11146: 11074: 11068: 11030: 11016: 10989: 10981: 10959: 10955: 10947: 10929: 10916: 10859: 10847:Dihydrochalcone 10841: 10809: 10782: 10759: 10723: 10699: 10671: 10648: 10627: 10619: 10598: 10590: 10561: 10543: 10516: 10493: 10452: 10446: 10414: 10406: 10400: 10362: 10319: 10313: 10273: 10272: 10267: 10244: 10222: 10205: 10174: 10130: 10070: 10068:Tetraterpenoids 10062: 10041: 9982: 9973:Cholecalciferol 9899: 9896:Geranylfarnesol 9878: 9861:Neoabietic acid 9846:Isopimaric acid 9821: 9795: 9765: 9740: 9719: 9685: 9620: 9579: 9528: 9479: 9478:Monoterpenoids 9469: 9424: 9398: 9374: 9370: 9366: 9358: 9354:Isovaleric acid 9344: 9340: 9320: 9277: 9262: 9222: 9216: 9186: 9181: 9159: 9150:Tolfenamic acid 9070:Flufenamic acid 8966: 8873:Resiniferatoxin 8866:Ruta graveolens 8629:Diacyl glycerol 8424: 8408: 8370: 8366: 8346: 8332: 8282: 8268:Tolfenamic acid 8261:Ruta graveolens 8201:Flufenamic acid 8164: 8113:Ruta graveolens 8024:(intracellular) 7985: 7981:Tolfenamic acid 7936:Flufenamic acid 7914: 7890:Diacyl glycerol 7853: 7797: 7483:Cannabichromene 7393:4-Oxo-2-nonenal 7365: 7354: 7324: 7319: 7318: 7303:Clinical trials 7282: 7263:Phenazopyridine 7201: 7182:Cyclobenzaprine 7154: 7136: 7118: 7061:Sodium blockers 7055: 7003: 6996: 6954: 6913: 6903: 6862: 6852: 6746: 6742:Tolfenamic acid 6727:Flufenamic acid 6713: 6678: 6662: 6632: 6598: 6562: 6522: 6509: 6501: 6463: 6427:+metoclopramide 6368: 6349: 6170: 6129: 6068: 6051:Dihydromorphine 6040: 6012: 5988: 5920: 5906: 5864: 5859: 5853: 5836: 5834:Further reading 5831: 5830: 5797:nicotine]. 5744:Henri Braconnot 5665:Capsicum annuum 5637: 5633: 5628: 5623: 5622: 5575: 5571: 5526: 5522: 5477: 5473: 5426: 5422: 5367: 5363: 5353: 5351: 5343: 5342: 5338: 5285: 5281: 5230: 5226: 5181: 5177: 5167: 5165: 5157: 5156: 5152: 5105: 5101: 5050: 5046: 4991: 4987: 4942: 4938: 4907: 4903: 4871: 4867: 4860: 4838: 4834: 4803:Capsicum annuum 4797: 4793: 4774:J. Chem. Soc. C 4770: 4761: 4724: 4720: 4693: 4689: 4646: 4642: 4611: 4607: 4572: 4568: 4545: 4541: 4518: 4514: 4483: 4472: 4467: 4463: 4436: 4432: 4417:J. Chem. Soc. C 4413: 4409: 4398: 4394: 4359: 4355: 4340:Capsicum annuum 4336: 4332: 4317: 4313: 4294: 4290: 4271: 4267: 4234: 4230: 4197: 4193: 4170: 4166: 4139: 4135: 4108: 4104: 4091:(12): 818–829. 4077: 4073: 4065: 4051: 4047: 4004: 4002: 3998: 3931: 3898: 3894: 3879: 3875: 3860: 3856: 3846: 3844: 3839: 3838: 3834: 3781: 3777: 3754: 3750: 3740: 3738: 3733: 3732: 3719: 3672: 3668: 3653: 3652: 3648: 3633: 3632: 3628: 3589: 3585: 3546: 3542: 3499: 3495: 3480: 3476: 3469: 3455: 3451: 3428: 3424: 3379: 3375: 3365: 3363: 3359: 3351: 3350: 3341: 3331: 3329: 3326:BBC News Online 3320: 3319: 3312: 3265: 3261: 3251: 3249: 3244: 3243: 3239: 3208: 3204: 3194: 3192: 3188: 3181: 3177: 3176: 3169: 3132: 3128: 3089: 3085: 3054: 3050: 3005: 3001: 2991: 2989: 2985: 2947:(1): CD007393. 2936: 2930: 2926: 2916: 2914: 2907: 2903: 2893: 2891: 2879: 2878: 2874: 2860: 2856: 2847: 2845: 2832: 2831: 2827: 2817: 2815: 2806: 2805: 2801: 2754: 2741: 2696: 2689: 2679: 2677: 2667: 2656: 2609: 2605: 2550: 2546: 2507: 2498: 2488: 2486: 2477: 2476: 2469: 2456: 2455: 2451: 2419: 2412: 2402: 2400: 2387: 2386: 2382: 2372: 2370: 2361: 2360: 2356: 2346: 2344: 2339: 2338: 2321: 2311: 2309: 2304: 2303: 2299: 2294: 2267:Carolina Reaper 2254:Resiniferatoxin 2222: 2209: 2197: 2185: 2166: 2120: 2094:phenylpropanoid 2083:acyltransferase 2051: 2031:phenylpropanoid 2026: 1989: 1841: 1834: 1832: 1802:) are the most 1793: 1787: 1771:Rudolf Buchheim 1763: 1707: 1695: 1683: 1659: 1636: 1616: 1608: 1603: 1587: 1553: 1530:LDL cholesterol 1522:clinical trials 1436: 1360: 1354: 1349: 1279: 1207: 1203: 1169: 1165: 1136: 1122: 1115: 1110: 1109: 1108:  ?) 1099: 1095: 1091: 1087: 1066: 1065: 1064: 1063: 1056: 1049: 1042: 1038: 1030: 955: 929: 915: 884: 859: 834: 782: 765: 747: 734: 728: 726: 716: 704: 673: 669: 665: 653: 632:Highly pungent 611: 601: 592: 586: 578: 564: 561: 556: 555: 544: 541: 540: 537: 531: 530: 527: 521: 520: 509: 491: 484: 475: 455: 442: 430: 410: 397: 388: 351: 331: 311: 291: 268: 259: 246: 235: 222: 208: 206: 204: 202: 196: 187: 177: 161: 160: 106: 102: 68: 64: 28: 23: 22: 15: 12: 11: 5: 14937: 14927: 14926: 14921: 14916: 14901: 14900: 14877: 14876: 14874: 14873: 14863: 14852: 14849: 14848: 14846: 14845: 14843:Scoville scale 14840: 14835: 14830: 14825: 14820: 14815: 14810: 14804: 14802: 14798: 14797: 14795: 14794: 14789: 14784: 14779: 14774: 14769: 14764: 14759: 14754: 14749: 14744: 14739: 14733: 14731: 14724: 14723: 14721: 14720: 14715: 14710: 14705: 14700: 14695: 14690: 14685: 14680: 14675: 14670: 14665: 14660: 14655: 14649: 14647: 14643: 14642: 14635: 14633: 14630: 14629: 14627: 14626: 14624:Tabasco pepper 14621: 14616: 14611: 14606: 14600: 14598: 14590: 14589: 14587: 14586: 14581: 14576: 14571: 14566: 14561: 14556: 14551: 14546: 14541: 14536: 14531: 14526: 14521: 14516: 14511: 14506: 14501: 14496: 14495:(ghost pepper) 14490: 14485: 14480: 14474: 14472: 14464: 14463: 14461: 14460: 14455: 14450: 14448:Bishop's crown 14444: 14442: 14434: 14433: 14431: 14430: 14425: 14420: 14415: 14410: 14405: 14400: 14395: 14390: 14385: 14380: 14375: 14370: 14369: 14368: 14363: 14358: 14353: 14348: 14338: 14333: 14328: 14323: 14318: 14313: 14308: 14303: 14298: 14293: 14288: 14283: 14278: 14276:Chile de árbol 14273: 14268: 14263: 14258: 14253: 14248: 14243: 14238: 14233: 14228: 14222: 14220: 14209: 14203: 14202: 14195: 14194: 14187: 14180: 14172: 14163: 14162: 14152: 14149: 14148: 14146: 14145: 14140: 14135: 14130: 14125: 14120: 14115: 14110: 14108:Trichostatin A 14105: 14100: 14095: 14090: 14085: 14080: 14075: 14070: 14065: 14060: 14055: 14050: 14048:Phenylbutyrate 14045: 14040: 14035: 14030: 14025: 14020: 14015: 14010: 14005: 14000: 13995: 13990: 13985: 13980: 13975: 13970: 13965: 13960: 13955: 13950: 13945: 13940: 13934: 13931: 13930: 13923: 13922: 13915: 13908: 13900: 13891: 13890: 13888: 13887: 13881: 13875: 13873: 13866: 13865: 13863: 13862: 13857: 13852: 13846: 13844: 13840: 13839: 13837: 13836: 13831: 13826: 13824:Hydroxytyrosol 13821: 13815: 13813: 13807: 13806: 13803: 13802: 13800: 13799: 13794: 13789: 13784: 13779: 13774: 13769: 13763: 13761: 13755: 13754: 13752: 13751: 13749:Sinapinic acid 13746: 13741: 13736: 13731: 13726: 13721: 13716: 13711: 13706: 13700: 13698: 13692: 13691: 13688: 13687: 13685: 13684: 13679: 13673: 13671: 13667: 13666: 13664: 13663: 13658: 13653: 13648: 13643: 13638: 13633: 13628: 13623: 13618: 13612: 13610: 13604: 13603: 13601: 13600: 13595: 13590: 13585: 13580: 13575: 13570: 13565: 13560: 13553: 13551: 13545: 13544: 13541: 13540: 13538: 13537: 13531: 13529: 13525: 13524: 13522: 13521: 13519:Salicylic acid 13516: 13511: 13505: 13503: 13496: 13487: 13485:Phenolic acids 13481: 13480: 13477:Aromatic acids 13473: 13472: 13465: 13458: 13450: 13444: 13442:Aromatic acids 13438: 13437: 13434: 13433: 13428: 13426: 13419: 13418: 13416: 13415: 13406: 13400: 13394: 13388: 13383: 13377: 13375:Anthraquinones 13372: 13365: 13363: 13359: 13358: 13355: 13354: 13352: 13351: 13350: 13349: 13344: 13339: 13334: 13326: 13321: 13319:Pseudo tannins 13316: 13314:Tannin sources 13310: 13308: 13304: 13303: 13301: 13300: 13295: 13289: 13287: 13279: 13278: 13276: 13275: 13272: 13267: 13262: 13257: 13252: 13247: 13242: 13237: 13232: 13227: 13222: 13217: 13212: 13206: 13204: 13198: 13197: 13195: 13194: 13189: 13184: 13179: 13174: 13168: 13166: 13160: 13159: 13156: 13155: 13153: 13152: 13147: 13141: 13139: 13133: 13132: 13130: 13129: 13124: 13119: 13114: 13109: 13104: 13099: 13094: 13089: 13084: 13078: 13076: 13067: 13061: 13060: 13052: 13051: 13044: 13037: 13029: 13023: 13017: 13016: 13011: 13009: 13003: 13002: 13000: 12999: 12994: 12989: 12984: 12978: 12976: 12968: 12967: 12965: 12964: 12959: 12954: 12948: 12946: 12942: 12934: 12933: 12928: 12926: 12924:Flavonolignans 12920: 12919: 12916: 12915: 12910: 12907: 12906: 12903: 12902: 12900: 12899: 12894: 12892:Methylenedioxy 12889: 12884: 12879: 12874: 12869: 12864: 12858: 12856: 12850: 12849: 12846: 12845: 12843: 12842: 12836: 12834: 12828: 12827: 12825: 12824: 12813: 12811: 12802: 12796: 12795: 12793: 12792: 12787: 12781: 12779: 12773: 12772: 12769: 12768: 12766: 12765: 12762:Guibourtinidin 12754: 12752: 12746: 12745: 12743: 12742: 12731: 12729: 12720: 12718:Anthocyanidins 12714: 12713: 12710: 12709: 12707: 12706: 12700: 12694: 12692: 12686: 12685: 12683: 12682: 12677: 12672: 12666: 12664: 12658: 12657: 12655: 12654: 12643: 12641: 12635: 12634: 12632: 12631: 12620: 12618: 12606: 12605: 12603: 12602: 12591: 12589: 12577: 12576: 12574: 12573: 12567: 12565: 12558: 12552: 12551: 12548: 12547: 12545: 12544: 12538: 12536: 12530: 12529: 12527: 12526: 12511: 12509: 12503: 12502: 12500: 12499: 12488: 12486: 12480: 12479: 12477: 12476: 12465: 12463: 12454: 12445: 12439: 12438: 12430: 12429: 12422: 12415: 12407: 12401: 12393: 12392: 12384: 12383: 12376: 12369: 12361: 12355: 12349: 12348: 12346: 12345: 12340: 12335: 12330: 12325: 12320: 12314: 12312: 12306: 12305: 12297: 12296: 12289: 12282: 12274: 12265: 12264: 12259: 12257: 12250: 12249: 12247: 12246: 12245: 12244: 12239: 12234: 12233: 12232: 12222: 12221: 12220: 12215: 12200: 12199: 12198: 12193: 12182: 12180: 12174: 12173: 12171: 12170: 12165: 12160: 12155: 12150: 12148:Anacardic acid 12145: 12140: 12135: 12134: 12133: 12128: 12119: 12117: 12111: 12110: 12108: 12107: 12101: 12099: 12093: 12092: 12090: 12089: 12088: 12087: 12082: 12072: 12071: 12070: 12059: 12057: 12051: 12050: 12048: 12047: 12046: 12045: 12040: 12035: 12030: 12025: 12020: 12015: 12005: 12004: 12003: 12002: 12001: 11991: 11984:Organosulfides 11981: 11980: 11979: 11974: 11969: 11968: 11967: 11962: 11957: 11944: 11943: 11942: 11937: 11932: 11920: 11918: 11916:Glucosinolates 11912: 11911: 11906: 11905: 11903: 11902: 11896: 11890: 11888: 11881: 11880: 11878: 11877: 11872: 11867: 11861: 11859: 11855: 11854: 11852: 11851: 11846: 11841: 11839:Hydroxytyrosol 11836: 11830: 11828: 11822: 11821: 11818: 11817: 11815: 11814: 11809: 11804: 11799: 11794: 11789: 11784: 11778: 11776: 11770: 11769: 11767: 11766: 11764:Sinapinic acid 11761: 11756: 11751: 11746: 11741: 11736: 11731: 11726: 11721: 11715: 11713: 11707: 11706: 11703: 11702: 11700: 11699: 11694: 11688: 11686: 11682: 11681: 11679: 11678: 11673: 11668: 11663: 11658: 11653: 11648: 11643: 11638: 11633: 11627: 11625: 11619: 11618: 11616: 11615: 11610: 11605: 11600: 11595: 11590: 11585: 11580: 11575: 11568: 11566: 11560: 11559: 11556: 11555: 11553: 11552: 11546: 11544: 11540: 11539: 11537: 11536: 11534:Salicylic acid 11531: 11526: 11520: 11518: 11511: 11502: 11500:Phenolic acids 11496: 11495: 11492:Aromatic acids 11488: 11487: 11480: 11473: 11465: 11459: 11457:Aromatic acids 11453: 11452: 11449: 11448: 11443: 11441: 11434: 11433: 11431: 11430: 11421: 11415: 11409: 11403: 11398: 11392: 11390:Anthraquinones 11387: 11380: 11378: 11374: 11373: 11370: 11369: 11367: 11366: 11365: 11364: 11359: 11354: 11349: 11341: 11336: 11334:Pseudo tannins 11331: 11329:Tannin sources 11325: 11323: 11319: 11318: 11316: 11315: 11310: 11304: 11302: 11294: 11293: 11291: 11290: 11287: 11282: 11277: 11272: 11267: 11262: 11257: 11252: 11247: 11242: 11237: 11232: 11227: 11221: 11219: 11213: 11212: 11210: 11209: 11204: 11199: 11194: 11189: 11183: 11181: 11175: 11174: 11171: 11170: 11168: 11167: 11162: 11156: 11154: 11148: 11147: 11145: 11144: 11139: 11134: 11129: 11124: 11119: 11114: 11109: 11104: 11099: 11093: 11091: 11082: 11076: 11075: 11067: 11066: 11059: 11052: 11044: 11038: 11032: 11031: 11026: 11024: 11018: 11017: 11015: 11014: 11009: 11004: 10999: 10993: 10991: 10983: 10982: 10980: 10979: 10974: 10969: 10963: 10961: 10957: 10949: 10948: 10943: 10941: 10939:Flavonolignans 10935: 10934: 10931: 10930: 10925: 10922: 10921: 10918: 10917: 10915: 10914: 10909: 10907:Methylenedioxy 10904: 10899: 10894: 10889: 10884: 10879: 10873: 10871: 10865: 10864: 10861: 10860: 10858: 10857: 10851: 10849: 10843: 10842: 10840: 10839: 10828: 10826: 10817: 10811: 10810: 10808: 10807: 10802: 10796: 10794: 10788: 10787: 10784: 10783: 10781: 10780: 10777:Guibourtinidin 10769: 10767: 10761: 10760: 10758: 10757: 10746: 10744: 10735: 10733:Anthocyanidins 10729: 10728: 10725: 10724: 10722: 10721: 10715: 10709: 10707: 10701: 10700: 10698: 10697: 10692: 10687: 10681: 10679: 10673: 10672: 10670: 10669: 10658: 10656: 10650: 10649: 10647: 10646: 10635: 10633: 10621: 10620: 10618: 10617: 10606: 10604: 10592: 10591: 10589: 10588: 10582: 10580: 10573: 10567: 10566: 10563: 10562: 10560: 10559: 10553: 10551: 10545: 10544: 10542: 10541: 10526: 10524: 10518: 10517: 10515: 10514: 10503: 10501: 10495: 10494: 10492: 10491: 10480: 10478: 10469: 10460: 10454: 10453: 10445: 10444: 10437: 10430: 10422: 10416: 10408: 10407: 10399: 10398: 10391: 10384: 10376: 10370: 10364: 10363: 10361: 10360: 10355: 10350: 10345: 10340: 10335: 10329: 10327: 10321: 10320: 10312: 10311: 10304: 10297: 10289: 10283: 10281: 10275: 10274: 10269: 10268: 10266: 10265: 10259: 10252: 10250: 10246: 10245: 10243: 10242: 10239:protein domain 10230: 10228: 10224: 10223: 10221: 10220: 10217: 10213: 10211: 10207: 10206: 10204: 10203: 10200: 10195: 10193:Natural rubber 10189: 10187: 10184:Polyterpenoids 10180: 10179: 10176: 10175: 10173: 10172: 10167: 10162: 10157: 10152: 10147: 10141: 10139: 10132: 10131: 10129: 10128: 10123: 10118: 10113: 10108: 10106:Delta-Carotene 10103: 10101:Gamma-Carotene 10098: 10093: 10091:Alpha-Carotene 10087: 10085: 10076: 10064: 10063: 10061: 10060: 10057: 10053: 10051: 10047: 10046: 10043: 10042: 10040: 10039: 10038: 10037: 10032: 10030:Betulinic acid 10027: 10022: 10020:Oleanolic acid 10014: 10009: 10006: 10001: 9996: 9990: 9988: 9984: 9983: 9981: 9980: 9975: 9970: 9965: 9960: 9955: 9954: 9953: 9948: 9943: 9938: 9933: 9932:Citrostadienol 9930: 9919: 9917: 9908: 9901: 9900: 9898: 9897: 9893: 9891: 9884: 9883: 9880: 9879: 9877: 9876: 9875:Palustric acid 9873: 9870: 9867: 9862: 9859: 9856: 9851: 9848: 9843: 9840: 9837: 9831: 9829: 9823: 9822: 9820: 9819: 9814: 9809: 9803: 9801: 9797: 9796: 9794: 9793: 9790: 9787: 9784: 9779: 9773: 9771: 9767: 9766: 9764: 9763: 9758: 9755: 9748: 9746: 9742: 9741: 9739: 9738: 9733: 9727: 9725: 9721: 9720: 9718: 9717: 9714: 9709: 9703: 9701: 9694: 9687: 9686: 9684: 9683: 9680: 9677: 9672: 9669: 9664: 9661: 9656: 9651: 9646: 9641: 9635: 9633: 9626: 9625: 9622: 9621: 9619: 9618: 9613: 9608: 9603: 9601:Bornyl acetate 9598: 9593: 9587: 9585: 9581: 9580: 9578: 9577: 9572: 9567: 9562: 9552: 9547: 9542: 9536: 9534: 9530: 9529: 9527: 9526: 9521: 9516: 9511: 9506: 9501: 9496: 9490: 9488: 9481: 9475: 9474: 9471: 9470: 9468: 9467: 9462: 9457: 9452: 9447: 9432: 9430: 9426: 9425: 9423: 9422: 9417: 9412: 9406: 9404: 9400: 9399: 9397: 9396: 9391: 9385: 9383: 9376: 9372: 9368: 9360: 9359: 9357: 9356: 9351: 9346: 9342: 9338: 9331: 9329: 9326:Hemiterpenoids 9322: 9321: 9319: 9318: 9312: 9309: 9303: 9300: 9297: 9285: 9283: 9279: 9278: 9261: 9260: 9253: 9246: 9238: 9232: 9230: 9224: 9223: 9220:phytochemicals 9215: 9214: 9207: 9200: 9192: 9183: 9182: 9168: 9165: 9164: 9161: 9160: 9158: 9157: 9152: 9147: 9142: 9137: 9132: 9127: 9122: 9117: 9112: 9107: 9102: 9097: 9092: 9087: 9082: 9077: 9072: 9067: 9062: 9057: 9052: 9047: 9037: 9027: 9017: 9007: 9002: 8997: 8992: 8987: 8974: 8972: 8968: 8967: 8965: 8964: 8959: 8949: 8944: 8928: 8914: 8904: 8886: 8870: 8858: 8853: 8848: 8843: 8840:Dorrigo pepper 8833: 8819: 8812:Phorbol esters 8809: 8804: 8799: 8789: 8779: 8769: 8764: 8759: 8754: 8744: 8737: 8732: 8722: 8712: 8702: 8697: 8692: 8687: 8682: 8672: 8660: 8646: 8641: 8631: 8626: 8621: 8599: 8589: 8582:Cannabidivarin 8579: 8569: 8550:camphor laurel 8543: 8531: 8526: 8521: 8511: 8493: 8488: 8483: 8478: 8473: 8468: 8463: 8458: 8453: 8447: 8445: 8438: 8430: 8429: 8426: 8425: 8423: 8422: 8416: 8414: 8410: 8409: 8407: 8406: 8393: 8391: 8384: 8376: 8375: 8372: 8371: 8369: 8368: 8364: 8360: 8354: 8352: 8348: 8347: 8345: 8344: 8339: 8334: 8330: 8326: 8321: 8316: 8311: 8305: 8303: 8296: 8288: 8287: 8284: 8283: 8281: 8280: 8275: 8270: 8265: 8253: 8248: 8243: 8238: 8233: 8228: 8218: 8213: 8211:Mefenamic acid 8208: 8203: 8198: 8193: 8188: 8183: 8178: 8172: 8170: 8166: 8165: 8163: 8162: 8157: 8152: 8133: 8117: 8105: 8100: 8095: 8085: 8080: 8075: 8070: 8065: 8060: 8055: 8045: 8040: 8035: 8030: 8025: 8019: 8014: 8008: 8006: 7999: 7991: 7990: 7987: 7986: 7984: 7983: 7978: 7973: 7968: 7963: 7958: 7953: 7948: 7943: 7938: 7933: 7928: 7922: 7920: 7916: 7915: 7913: 7912: 7907: 7904:St John's wort 7897: 7892: 7887: 7884:St John's wort 7876: 7874: 7867: 7859: 7858: 7855: 7854: 7852: 7851: 7846: 7841: 7831: 7826: 7816: 7811: 7805: 7803: 7799: 7798: 7796: 7795: 7790: 7780: 7770: 7765: 7755: 7750: 7732: 7729:Dorrigo pepper 7722: 7717: 7712: 7707: 7697: 7687: 7677: 7672: 7662: 7657: 7650:Sichuan pepper 7643: 7627: 7622: 7620:Isothiocyanate 7617: 7612: 7607: 7602: 7597: 7587: 7582: 7577: 7565: 7560: 7550: 7540: 7530: 7525: 7520: 7513:Cinnamaldehyde 7510: 7500: 7490: 7480: 7475: 7470: 7465: 7443: 7433: 7428: 7410: 7405: 7400: 7395: 7390: 7384: 7382: 7375: 7367: 7366: 7353: 7352: 7345: 7338: 7330: 7321: 7320: 7317: 7316: 7315: 7314: 7311: 7300: 7294: 7288: 7287: 7284: 7283: 7281: 7280: 7275: 7270: 7265: 7260: 7258:Methoxyflurane 7255: 7250: 7245: 7240: 7235: 7230: 7225: 7220: 7215: 7209: 7207: 7203: 7202: 7200: 7199: 7194: 7189: 7184: 7179: 7174: 7168: 7166: 7160: 7159: 7156: 7155: 7153: 7152: 7146: 7144: 7138: 7137: 7135: 7134: 7129: 7124: 7116: 7111: 7110: 7100: 7095: 7090: 7076: 7071: 7065: 7063: 7057: 7056: 7054: 7053: 7048: 7043: 7038: 7033: 7028: 7023: 7017: 7015: 7006: 6998: 6997: 6995: 6994: 6989: 6984: 6979: 6974: 6968: 6966: 6960: 6959: 6956: 6955: 6953: 6952: 6947: 6942: 6937: 6932: 6927: 6921: 6919: 6915: 6914: 6912: 6911: 6901:Propyphenazone 6898: 6893: 6888: 6883: 6878: 6876:Aminophenazone 6872: 6870: 6864: 6863: 6861: 6860: 6847: 6842: 6837: 6832: 6827: 6822: 6817: 6812: 6807: 6802: 6797: 6792: 6787: 6782: 6777: 6772: 6767: 6756: 6754: 6748: 6747: 6745: 6744: 6739: 6737:Mefenamic acid 6734: 6729: 6723: 6721: 6715: 6714: 6712: 6711: 6706: 6701: 6696: 6691: 6686: 6672: 6670: 6664: 6663: 6661: 6660: 6655: 6650: 6645: 6640: 6627: 6622: 6617: 6612: 6606: 6604: 6600: 6599: 6597: 6596: 6591: 6586: 6581: 6576: 6570: 6568: 6564: 6563: 6561: 6560: 6555: 6550: 6545: 6540: 6535: 6530: 6517: 6496: 6491: 6486: 6480: 6478: 6471: 6465: 6464: 6462: 6461: 6456: 6451: 6446: 6445: 6444: 6439: 6434: 6429: 6424: 6419: 6414: 6409: 6399: 6394: 6389: 6383: 6381: 6374: 6373: 6370: 6369: 6367: 6366: 6361: 6344: 6339: 6334: 6329: 6324: 6319: 6314: 6309: 6304: 6299: 6294: 6289: 6284: 6279: 6274: 6269: 6264: 6259: 6254: 6249: 6244: 6234: 6229: 6224: 6219: 6214: 6209: 6207:Dextromoramide 6204: 6199: 6194: 6189: 6184: 6178: 6176: 6172: 6171: 6169: 6168: 6163: 6158: 6153: 6124: 6119: 6114: 6109: 6104: 6099: 6094: 6089: 6087:Hydromorphinol 6084: 6063: 6058: 6053: 6048: 6038:Dihydrocodeine 6035: 6030: 6025: 6020: 6007: 6005:Benzylmorphine 6002: 5996: 5994: 5990: 5989: 5987: 5986: 5981: 5976: 5971: 5961: 5960: 5959: 5954: 5943: 5941: 5928: 5922: 5921: 5905: 5904: 5897: 5890: 5882: 5876: 5875: 5870: 5863: 5862:External links 5860: 5858: 5857: 5851: 5837: 5835: 5832: 5829: 5828: 5826: 5825: 5824: 5823: 5792: 5767: 5741: 5700: 5699: 5696: 5689: 5677: 5661: 5650: 5630: 5629: 5627: 5624: 5621: 5620: 5569: 5540:(3): 487–492. 5520: 5471: 5420: 5361: 5336: 5279: 5224: 5195:(3): 169–177. 5175: 5150: 5099: 5044: 4985: 4956:(3): 154–162. 4936: 4901: 4865: 4858: 4832: 4791: 4759: 4738:(5): 675–688. 4718: 4687: 4640: 4605: 4586:(4): 839–844. 4580:Phytochemistry 4566: 4539: 4512: 4470: 4461: 4450:(4): 425–426. 4430: 4407: 4392: 4353: 4330: 4311: 4288: 4265: 4228: 4191: 4180:(3): 737–743. 4164: 4133: 4122:(5): 411–412. 4102: 4071: 4063: 4045: 3996: 3994: 3993: 3984: 3971: 3965: 3924:. 3rd Series. 3913: 3907:. 3rd Series. 3892: 3873: 3854: 3832: 3775: 3764:(4): 326–333. 3748: 3717: 3666: 3663:. 16 May 2024. 3646: 3626: 3599:(4): 275–328. 3583: 3540: 3513:(1): R77–R85. 3493: 3474: 3467: 3449: 3438:(4): 248–249. 3422: 3373: 3339: 3310: 3259: 3237: 3224:10.1002/ps.705 3202: 3167: 3126: 3099:(8): 858–865. 3083: 3064:(3): 438–442. 3048: 2999: 2924: 2901: 2881:"Qutenza EPAR" 2872: 2870: 2869: 2844:. 29 June 2010 2825: 2799: 2739: 2687: 2675:New York Times 2654: 2603: 2544: 2496: 2467: 2449: 2430:(6): 435–474. 2410: 2380: 2354: 2319: 2296: 2295: 2293: 2290: 2289: 2288: 2283: 2274: 2256: 2247: 2241: 2221: 2218: 2208: 2205: 2196: 2193: 2184: 2181: 2165: 2162: 2119: 2116: 2050: 2047: 2025: 2022: 1988: 1985: 1982: 1981: 1974: 1971: 1969: 1966: 1960: 1959: 1952: 1949: 1946: 1943: 1937: 1936: 1929: 1926: 1923: 1920: 1914: 1913: 1906: 1903: 1900: 1897: 1891: 1890: 1883: 1880: 1877: 1874: 1868: 1867: 1860: 1857: 1854: 1851: 1847: 1846: 1843: 1836: 1829: 1824: 1786: 1783: 1762: 1759: 1739:depolarization 1706: 1703: 1694: 1691: 1682: 1679: 1658: 1655: 1635: 1632: 1624:conjunctivitis 1614: 1607: 1604: 1602: 1599: 1586: 1583: 1552: 1549: 1484:. A capsaicin 1448:dermal patches 1435: 1432: 1391:Scoville scale 1356:Main article: 1353: 1350: 1348: 1345: 1278: 1275: 1149: 1148: 1147:16,000,000 SHU 1145: 1143:Scoville scale 1139: 1138: 1133: 1129: 1128: 1120: 1117: 1116: 1111: 1089: 1088: 1084:standard state 1081: 1078: 1077: 1075: 1068: 1067: 1057: 1050: 1043: 1028: 1027: 1026: 1025: 1023: 1014: 1013: 983:P305+P351+P338 956: 951: 948: 947: 930: 925: 922: 921: 916: 911: 908: 907: 885: 880: 877: 876: 866: 865: 861: 860: 858: 857: 844: 842: 836: 835: 833: 832: 814: 812: 806: 805: 783: 778: 775: 774: 770: 769: 766: 761: 758: 757: 753: 752: 749: 745: 738: 737: 724: 722:Vapor pressure 718: 717: 715: 714: 702: 697: 686: 684: 678: 677: 666: 661: 658: 657: 650: 644: 643: 640: 634: 633: 630: 624: 623: 620: 616: 615: 609: 603: 602: 599: 590: 584: 579: 574: 571: 570: 566: 565: 563: 562: 559: 551: 550: 549: 546: 545: 543: 542: 538: 535: 534: 532: 528: 525: 524: 516: 515: 514: 511: 510: 508: 507: 494: 492: 480: 477: 476: 474: 473: 465: 463: 457: 456: 454: 453: 445: 443: 435: 432: 431: 429: 428: 420: 418: 412: 411: 409: 408: 400: 398: 393: 390: 389: 387: 386: 382: 380: 372: 371: 361: 353: 352: 350: 349: 341: 339: 333: 332: 330: 329: 321: 319: 313: 312: 310: 309: 301: 299: 293: 292: 290: 289: 281: 279: 273: 272: 269: 264: 261: 260: 258: 257: 249: 247: 240: 237: 236: 234: 233: 225: 223: 218: 215: 214: 210: 209: 167: 163: 162: 150: 149: 143: 142: 62: 61:Pronunciation 58: 57: 53: 52: 44: 43: 26: 9: 6: 4: 3: 2: 14936: 14925: 14922: 14920: 14917: 14915: 14914:Capsaicinoids 14912: 14911: 14909: 14899: 14889: 14888: 14885: 14872: 14864: 14862: 14854: 14853: 14850: 14844: 14841: 14839: 14836: 14834: 14831: 14829: 14826: 14824: 14821: 14819: 14816: 14814: 14811: 14809: 14806: 14805: 14803: 14799: 14793: 14790: 14788: 14787:Tabasco sauce 14785: 14783: 14780: 14778: 14775: 14773: 14770: 14768: 14765: 14763: 14760: 14758: 14755: 14753: 14750: 14748: 14745: 14743: 14740: 14738: 14737:Biber salçası 14735: 14734: 14732: 14729: 14725: 14719: 14716: 14714: 14711: 14709: 14706: 14704: 14701: 14699: 14696: 14694: 14691: 14689: 14686: 14684: 14681: 14679: 14676: 14674: 14671: 14669: 14666: 14664: 14661: 14659: 14656: 14654: 14651: 14650: 14648: 14646:Culinary uses 14644: 14639: 14625: 14622: 14620: 14619:Siling labuyo 14617: 14615: 14612: 14610: 14607: 14605: 14602: 14601: 14599: 14597: 14596: 14591: 14585: 14582: 14580: 14577: 14575: 14574:Scotch bonnet 14572: 14570: 14567: 14565: 14562: 14560: 14557: 14555: 14552: 14550: 14547: 14545: 14542: 14540: 14539:Komodo Dragon 14537: 14535: 14532: 14530: 14527: 14525: 14522: 14520: 14517: 14515: 14512: 14510: 14507: 14505: 14502: 14500: 14497: 14494: 14491: 14489: 14486: 14484: 14483:Ají caballero 14481: 14479: 14476: 14475: 14473: 14471: 14470: 14465: 14459: 14456: 14454: 14451: 14449: 14446: 14445: 14443: 14441: 14440: 14435: 14429: 14426: 14424: 14421: 14419: 14416: 14414: 14411: 14409: 14406: 14404: 14401: 14399: 14396: 14394: 14391: 14389: 14386: 14384: 14381: 14379: 14376: 14374: 14371: 14367: 14364: 14362: 14359: 14357: 14354: 14352: 14349: 14347: 14344: 14343: 14342: 14339: 14337: 14334: 14332: 14329: 14327: 14324: 14322: 14321:Hungarian wax 14319: 14317: 14316:Guntur Sannam 14314: 14312: 14309: 14307: 14304: 14302: 14299: 14297: 14294: 14292: 14291:Facing Heaven 14289: 14287: 14284: 14282: 14279: 14277: 14274: 14272: 14269: 14267: 14264: 14262: 14259: 14257: 14254: 14252: 14249: 14247: 14244: 14242: 14239: 14237: 14234: 14232: 14229: 14227: 14224: 14223: 14221: 14219: 14218: 14213: 14210: 14208: 14204: 14200: 14199:Chili peppers 14193: 14188: 14186: 14181: 14179: 14174: 14173: 14170: 14160: 14159: 14156: 14150: 14144: 14141: 14139: 14136: 14134: 14131: 14129: 14126: 14124: 14121: 14119: 14116: 14114: 14111: 14109: 14106: 14104: 14101: 14099: 14096: 14094: 14091: 14089: 14086: 14084: 14081: 14079: 14076: 14074: 14071: 14069: 14066: 14064: 14061: 14059: 14056: 14054: 14051: 14049: 14046: 14044: 14041: 14039: 14036: 14034: 14031: 14029: 14026: 14024: 14021: 14019: 14016: 14014: 14011: 14009: 14006: 14004: 14001: 13999: 13996: 13994: 13991: 13989: 13986: 13984: 13981: 13979: 13976: 13974: 13971: 13969: 13966: 13964: 13961: 13959: 13956: 13954: 13951: 13949: 13946: 13944: 13941: 13939: 13936: 13935: 13932: 13928: 13921: 13916: 13914: 13909: 13907: 13902: 13901: 13898: 13885: 13884:Phlorotannins 13882: 13880: 13877: 13876: 13874: 13871: 13867: 13861: 13858: 13856: 13853: 13851: 13848: 13847: 13845: 13841: 13835: 13832: 13830: 13827: 13825: 13822: 13820: 13817: 13816: 13814: 13812: 13808: 13798: 13795: 13793: 13790: 13788: 13785: 13783: 13780: 13778: 13775: 13773: 13770: 13768: 13767:phenylalanine 13765: 13764: 13762: 13760: 13756: 13750: 13747: 13745: 13742: 13740: 13737: 13735: 13734:Coumaric acid 13732: 13730: 13727: 13725: 13722: 13720: 13719:Cinnamic acid 13717: 13715: 13714:Chicoric acid 13712: 13710: 13707: 13705: 13702: 13701: 13699: 13697: 13693: 13683: 13680: 13678: 13675: 13674: 13672: 13668: 13662: 13659: 13657: 13656:Syringic acid 13654: 13652: 13649: 13647: 13644: 13642: 13639: 13637: 13634: 13632: 13631:Eudesmic acid 13629: 13627: 13626:Ethyl gallate 13624: 13622: 13621:Chebulic acid 13619: 13617: 13614: 13613: 13611: 13609: 13605: 13599: 13596: 13594: 13591: 13589: 13586: 13584: 13583:Gentisic acid 13581: 13579: 13576: 13574: 13571: 13569: 13566: 13564: 13561: 13558: 13555: 13554: 13552: 13550: 13546: 13536: 13533: 13532: 13530: 13526: 13520: 13517: 13515: 13512: 13510: 13507: 13506: 13504: 13500: 13497: 13495: 13491: 13488: 13486: 13482: 13478: 13471: 13466: 13464: 13459: 13457: 13452: 13451: 13448: 13445: 13443: 13439: 13431: 13427: 13424: 13420: 13414: 13410: 13407: 13404: 13401: 13398: 13395: 13392: 13389: 13387: 13384: 13381: 13378: 13376: 13373: 13370: 13367: 13366: 13364: 13360: 13348: 13345: 13343: 13340: 13338: 13335: 13333: 13330: 13329: 13327: 13325: 13322: 13320: 13317: 13315: 13312: 13311: 13309: 13305: 13299: 13298:Acutissimin A 13296: 13294: 13291: 13290: 13288: 13284: 13280: 13273: 13271: 13270:7-Phloroeckol 13268: 13266: 13263: 13261: 13258: 13256: 13253: 13251: 13248: 13246: 13243: 13241: 13238: 13236: 13233: 13231: 13228: 13226: 13223: 13221: 13218: 13216: 13213: 13211: 13208: 13207: 13205: 13203: 13202:Phlorotannins 13199: 13193: 13190: 13188: 13185: 13183: 13180: 13178: 13175: 13173: 13170: 13169: 13167: 13165: 13161: 13151: 13148: 13146: 13143: 13142: 13140: 13138: 13134: 13128: 13125: 13123: 13120: 13118: 13115: 13113: 13110: 13108: 13105: 13103: 13100: 13098: 13095: 13093: 13090: 13088: 13085: 13083: 13080: 13079: 13077: 13075: 13074:Ellagitannins 13071: 13068: 13066: 13062: 13058: 13050: 13045: 13043: 13038: 13036: 13031: 13030: 13027: 13024: 13022: 13018: 13014: 13010: 13008: 13004: 12998: 12995: 12993: 12990: 12988: 12987:Pterostilbene 12985: 12983: 12980: 12979: 12977: 12973: 12969: 12963: 12960: 12958: 12955: 12953: 12950: 12949: 12947: 12939: 12935: 12931: 12927: 12925: 12921: 12913: 12908: 12898: 12895: 12893: 12890: 12888: 12885: 12883: 12880: 12878: 12875: 12873: 12870: 12868: 12865: 12863: 12860: 12859: 12857: 12855: 12854:Miscellaneous 12851: 12841: 12838: 12837: 12835: 12833: 12829: 12822: 12818: 12815: 12814: 12812: 12810: 12806: 12803: 12801: 12797: 12791: 12788: 12786: 12783: 12782: 12780: 12778: 12774: 12763: 12759: 12756: 12755: 12753: 12751: 12747: 12740: 12736: 12733: 12732: 12730: 12728: 12724: 12721: 12719: 12715: 12704: 12701: 12699: 12696: 12695: 12693: 12691: 12687: 12681: 12678: 12676: 12673: 12671: 12668: 12667: 12665: 12663: 12659: 12652: 12648: 12647:Leucocyanidin 12645: 12644: 12642: 12640: 12636: 12629: 12625: 12622: 12621: 12619: 12616: 12611: 12607: 12600: 12599:Gallocatechol 12596: 12593: 12592: 12590: 12587: 12582: 12578: 12572: 12571:Luteoliflavan 12569: 12568: 12566: 12562: 12559: 12557: 12553: 12543: 12540: 12539: 12537: 12535: 12534:Neoflavonoids 12531: 12524: 12520: 12516: 12513: 12512: 12510: 12508: 12504: 12497: 12493: 12490: 12489: 12487: 12485: 12481: 12474: 12470: 12467: 12466: 12464: 12462: 12458: 12455: 12453: 12452:Anthoxanthins 12449: 12446: 12444: 12440: 12436: 12428: 12423: 12421: 12416: 12414: 12409: 12408: 12405: 12402: 12398: 12394: 12390: 12382: 12377: 12375: 12370: 12368: 12363: 12362: 12359: 12356: 12354: 12350: 12344: 12341: 12339: 12336: 12334: 12331: 12329: 12326: 12324: 12323:Benzenetriols 12321: 12319: 12316: 12315: 12313: 12311: 12307: 12303: 12295: 12290: 12288: 12283: 12281: 12276: 12275: 12272: 12262: 12258: 12255: 12251: 12243: 12240: 12238: 12235: 12231: 12228: 12227: 12226: 12223: 12219: 12216: 12214: 12211: 12210: 12209: 12206: 12205: 12204: 12201: 12197: 12194: 12192: 12189: 12188: 12187: 12184: 12183: 12181: 12179: 12178:Carbohydrates 12175: 12169: 12168:Fertaric acid 12166: 12164: 12163:Coutaric acid 12161: 12159: 12158:Caftaric acid 12156: 12154: 12151: 12149: 12146: 12144: 12143:Tartaric acid 12141: 12139: 12136: 12132: 12129: 12127: 12124: 12123: 12121: 12120: 12118: 12116: 12115:Organic acids 12112: 12106: 12105:Chlorophyllin 12103: 12102: 12100: 12098: 12094: 12086: 12083: 12081: 12080:Indicaxanthin 12078: 12077: 12076: 12073: 12069: 12066: 12065: 12064: 12061: 12060: 12058: 12056: 12052: 12044: 12041: 12039: 12036: 12034: 12031: 12029: 12026: 12024: 12021: 12019: 12016: 12014: 12011: 12010: 12009: 12006: 12000: 11997: 11996: 11995: 11992: 11990: 11987: 11986: 11985: 11982: 11978: 11975: 11973: 11970: 11966: 11963: 11961: 11958: 11956: 11953: 11952: 11951: 11948: 11947: 11945: 11941: 11940:Glucoraphanin 11938: 11936: 11933: 11931: 11928: 11927: 11926: 11923:Precursor to 11922: 11921: 11919: 11917: 11913: 11900: 11899:Phlorotannins 11897: 11895: 11892: 11891: 11889: 11886: 11882: 11876: 11873: 11871: 11868: 11866: 11863: 11862: 11860: 11856: 11850: 11847: 11845: 11842: 11840: 11837: 11835: 11832: 11831: 11829: 11827: 11823: 11813: 11810: 11808: 11805: 11803: 11800: 11798: 11795: 11793: 11790: 11788: 11785: 11783: 11782:phenylalanine 11780: 11779: 11777: 11775: 11771: 11765: 11762: 11760: 11757: 11755: 11752: 11750: 11749:Coumaric acid 11747: 11745: 11742: 11740: 11737: 11735: 11734:Cinnamic acid 11732: 11730: 11729:Chicoric acid 11727: 11725: 11722: 11720: 11717: 11716: 11714: 11712: 11708: 11698: 11695: 11693: 11690: 11689: 11687: 11683: 11677: 11674: 11672: 11671:Syringic acid 11669: 11667: 11664: 11662: 11659: 11657: 11654: 11652: 11649: 11647: 11646:Eudesmic acid 11644: 11642: 11641:Ethyl gallate 11639: 11637: 11636:Chebulic acid 11634: 11632: 11629: 11628: 11626: 11624: 11620: 11614: 11611: 11609: 11606: 11604: 11601: 11599: 11598:Gentisic acid 11596: 11594: 11591: 11589: 11586: 11584: 11581: 11579: 11576: 11573: 11570: 11569: 11567: 11565: 11561: 11551: 11548: 11547: 11545: 11541: 11535: 11532: 11530: 11527: 11525: 11522: 11521: 11519: 11515: 11512: 11510: 11506: 11503: 11501: 11497: 11493: 11486: 11481: 11479: 11474: 11472: 11467: 11466: 11463: 11460: 11458: 11454: 11446: 11442: 11439: 11435: 11429: 11425: 11422: 11419: 11416: 11413: 11410: 11407: 11404: 11402: 11399: 11396: 11393: 11391: 11388: 11385: 11382: 11381: 11379: 11375: 11363: 11360: 11358: 11355: 11353: 11350: 11348: 11345: 11344: 11342: 11340: 11337: 11335: 11332: 11330: 11327: 11326: 11324: 11320: 11314: 11313:Acutissimin A 11311: 11309: 11306: 11305: 11303: 11299: 11295: 11288: 11286: 11285:7-Phloroeckol 11283: 11281: 11278: 11276: 11273: 11271: 11268: 11266: 11263: 11261: 11258: 11256: 11253: 11251: 11248: 11246: 11243: 11241: 11238: 11236: 11233: 11231: 11228: 11226: 11223: 11222: 11220: 11218: 11217:Phlorotannins 11214: 11208: 11205: 11203: 11200: 11198: 11195: 11193: 11190: 11188: 11185: 11184: 11182: 11180: 11176: 11166: 11163: 11161: 11158: 11157: 11155: 11153: 11149: 11143: 11140: 11138: 11135: 11133: 11130: 11128: 11125: 11123: 11120: 11118: 11115: 11113: 11110: 11108: 11105: 11103: 11100: 11098: 11095: 11094: 11092: 11090: 11089:Ellagitannins 11086: 11083: 11081: 11077: 11073: 11065: 11060: 11058: 11053: 11051: 11046: 11045: 11042: 11039: 11037: 11033: 11029: 11025: 11023: 11019: 11013: 11010: 11008: 11005: 11003: 11002:Pterostilbene 11000: 10998: 10995: 10994: 10992: 10988: 10984: 10978: 10975: 10973: 10970: 10968: 10965: 10964: 10962: 10954: 10950: 10946: 10942: 10940: 10936: 10928: 10923: 10913: 10910: 10908: 10905: 10903: 10900: 10898: 10895: 10893: 10890: 10888: 10885: 10883: 10880: 10878: 10875: 10874: 10872: 10870: 10869:Miscellaneous 10866: 10856: 10853: 10852: 10850: 10848: 10844: 10837: 10833: 10830: 10829: 10827: 10825: 10821: 10818: 10816: 10812: 10806: 10803: 10801: 10798: 10797: 10795: 10793: 10789: 10778: 10774: 10771: 10770: 10768: 10766: 10762: 10755: 10751: 10748: 10747: 10745: 10743: 10739: 10736: 10734: 10730: 10719: 10716: 10714: 10711: 10710: 10708: 10706: 10702: 10696: 10693: 10691: 10688: 10686: 10683: 10682: 10680: 10678: 10674: 10667: 10663: 10662:Leucocyanidin 10660: 10659: 10657: 10655: 10651: 10644: 10640: 10637: 10636: 10634: 10631: 10626: 10622: 10615: 10614:Gallocatechol 10611: 10608: 10607: 10605: 10602: 10597: 10593: 10587: 10586:Luteoliflavan 10584: 10583: 10581: 10577: 10574: 10572: 10568: 10558: 10555: 10554: 10552: 10550: 10549:Neoflavonoids 10546: 10539: 10535: 10531: 10528: 10527: 10525: 10523: 10519: 10512: 10508: 10505: 10504: 10502: 10500: 10496: 10489: 10485: 10482: 10481: 10479: 10477: 10473: 10470: 10468: 10467:Anthoxanthins 10464: 10461: 10459: 10455: 10451: 10443: 10438: 10436: 10431: 10429: 10424: 10423: 10420: 10417: 10413: 10409: 10405: 10397: 10392: 10390: 10385: 10383: 10378: 10377: 10374: 10371: 10369: 10365: 10359: 10356: 10354: 10351: 10349: 10346: 10344: 10341: 10339: 10338:Benzenetriols 10336: 10334: 10331: 10330: 10328: 10326: 10322: 10318: 10310: 10305: 10303: 10298: 10296: 10291: 10290: 10287: 10282: 10280: 10276: 10263: 10260: 10257: 10254: 10253: 10251: 10247: 10240: 10236: 10232: 10231: 10229: 10225: 10218: 10216:3-oxo-α-ionol 10215: 10214: 10212: 10208: 10201: 10199: 10196: 10194: 10191: 10190: 10188: 10185: 10181: 10171: 10168: 10166: 10163: 10161: 10158: 10156: 10153: 10151: 10150:Cryptoxanthin 10148: 10146: 10145:Canthaxanthin 10143: 10142: 10140: 10137: 10133: 10127: 10124: 10122: 10119: 10117: 10114: 10112: 10109: 10107: 10104: 10102: 10099: 10097: 10096:Beta-Carotene 10094: 10092: 10089: 10088: 10086: 10084: 10080: 10077: 10074: 10069: 10065: 10058: 10056:Ferrugicadiol 10055: 10054: 10052: 10048: 10036: 10033: 10031: 10028: 10026: 10023: 10021: 10018: 10017: 10015: 10013: 10010: 10008:Serratenediol 10007: 10005: 10002: 10000: 9997: 9995: 9992: 9991: 9989: 9985: 9979: 9976: 9974: 9971: 9969: 9966: 9964: 9961: 9959: 9956: 9952: 9949: 9947: 9944: 9942: 9939: 9937: 9934: 9931: 9929: 9926: 9925: 9924: 9921: 9920: 9918: 9916: 9912: 9909: 9906: 9905:Triterpenoids 9902: 9895: 9894: 9892: 9889: 9885: 9874: 9871: 9868: 9866: 9863: 9860: 9858:Mercusic acid 9857: 9855: 9852: 9849: 9847: 9844: 9841: 9839:Communic acid 9838: 9836: 9833: 9832: 9830: 9828: 9824: 9818: 9815: 9813: 9810: 9808: 9805: 9804: 9802: 9798: 9791: 9788: 9785: 9783: 9780: 9778: 9775: 9774: 9772: 9768: 9762: 9759: 9756: 9753: 9750: 9749: 9747: 9743: 9737: 9734: 9732: 9729: 9728: 9726: 9722: 9715: 9713: 9710: 9708: 9705: 9704: 9702: 9698: 9695: 9692: 9688: 9681: 9678: 9676: 9673: 9670: 9668: 9665: 9662: 9660: 9657: 9655: 9652: 9650: 9647: 9645: 9642: 9640: 9637: 9636: 9634: 9631: 9627: 9617: 9614: 9612: 9609: 9607: 9604: 9602: 9599: 9597: 9594: 9592: 9589: 9588: 9586: 9582: 9576: 9573: 9571: 9568: 9566: 9563: 9560: 9556: 9553: 9551: 9548: 9546: 9543: 9541: 9538: 9537: 9535: 9531: 9525: 9522: 9520: 9517: 9515: 9512: 9510: 9507: 9505: 9502: 9500: 9497: 9495: 9492: 9491: 9489: 9485: 9482: 9476: 9466: 9463: 9461: 9458: 9456: 9453: 9451: 9448: 9445: 9441: 9437: 9434: 9433: 9431: 9427: 9421: 9418: 9416: 9413: 9411: 9408: 9407: 9405: 9401: 9395: 9392: 9390: 9387: 9386: 9384: 9380: 9377: 9365: 9361: 9355: 9352: 9350: 9347: 9336: 9333: 9332: 9330: 9327: 9323: 9316: 9313: 9310: 9307: 9304: 9301: 9298: 9295: 9291: 9287: 9286: 9284: 9280: 9275: 9271: 9267: 9259: 9254: 9252: 9247: 9245: 9240: 9239: 9236: 9231: 9229: 9225: 9221: 9213: 9208: 9206: 9201: 9199: 9194: 9193: 9190: 9180: 9179: 9175: 9172: 9166: 9156: 9153: 9151: 9148: 9146: 9143: 9141: 9138: 9136: 9133: 9131: 9130:Ruthenium red 9128: 9126: 9123: 9121: 9118: 9116: 9113: 9111: 9110:Niflumic acid 9108: 9106: 9103: 9101: 9098: 9096: 9093: 9091: 9088: 9086: 9083: 9081: 9078: 9076: 9073: 9071: 9068: 9066: 9063: 9061: 9058: 9056: 9053: 9051: 9048: 9045: 9041: 9038: 9035: 9031: 9028: 9025: 9021: 9018: 9015: 9011: 9008: 9006: 9003: 9001: 8998: 8996: 8993: 8991: 8988: 8985: 8984: 8979: 8978:α-Spinasterol 8976: 8975: 8973: 8969: 8963: 8960: 8957: 8953: 8950: 8948: 8945: 8942: 8941: 8937: 8932: 8929: 8926: 8922: 8918: 8915: 8912: 8908: 8905: 8902: 8898: 8894: 8890: 8887: 8884: 8883: 8879: 8874: 8871: 8868: 8867: 8862: 8859: 8857: 8854: 8852: 8849: 8847: 8844: 8841: 8837: 8834: 8831: 8827: 8823: 8820: 8817: 8813: 8810: 8808: 8805: 8803: 8800: 8797: 8793: 8790: 8787: 8783: 8780: 8777: 8773: 8770: 8768: 8765: 8763: 8760: 8758: 8755: 8752: 8748: 8745: 8742: 8738: 8736: 8733: 8730: 8726: 8723: 8720: 8716: 8713: 8710: 8706: 8705:Homocapsaicin 8703: 8701: 8698: 8696: 8693: 8691: 8688: 8686: 8683: 8680: 8676: 8673: 8670: 8669: 8664: 8661: 8658: 8654: 8650: 8647: 8645: 8642: 8639: 8635: 8632: 8630: 8627: 8625: 8622: 8619: 8618:wild bergamot 8615: 8611: 8607: 8603: 8600: 8597: 8593: 8590: 8587: 8583: 8580: 8577: 8573: 8570: 8567: 8566:camphor basil 8563: 8559: 8555: 8551: 8547: 8544: 8541: 8540: 8535: 8532: 8530: 8527: 8525: 8522: 8519: 8515: 8512: 8509: 8505: 8501: 8497: 8494: 8492: 8489: 8487: 8484: 8482: 8479: 8477: 8474: 8472: 8469: 8467: 8464: 8462: 8459: 8457: 8454: 8452: 8449: 8448: 8446: 8442: 8439: 8436: 8431: 8421: 8420:Ruthenium red 8418: 8417: 8415: 8411: 8404: 8403: 8398: 8395: 8394: 8392: 8388: 8385: 8382: 8377: 8367: 8361: 8359: 8356: 8355: 8353: 8349: 8343: 8340: 8338: 8335: 8333: 8327: 8325: 8322: 8320: 8317: 8315: 8312: 8310: 8307: 8306: 8304: 8300: 8297: 8294: 8289: 8279: 8276: 8274: 8271: 8269: 8266: 8263: 8262: 8257: 8254: 8252: 8251:Ruthenium red 8249: 8247: 8244: 8242: 8239: 8237: 8234: 8232: 8231:Niflumic acid 8229: 8226: 8222: 8219: 8217: 8214: 8212: 8209: 8207: 8204: 8202: 8199: 8197: 8194: 8192: 8189: 8187: 8184: 8182: 8179: 8177: 8174: 8173: 8171: 8167: 8161: 8158: 8156: 8153: 8151:; indirectly) 8150: 8146: 8142: 8138: 8134: 8131: 8130: 8125: 8121: 8118: 8115: 8114: 8109: 8106: 8104: 8101: 8099: 8096: 8093: 8089: 8086: 8084: 8081: 8079: 8076: 8074: 8071: 8069: 8066: 8064: 8061: 8059: 8058:Frescolat MGA 8056: 8053: 8049: 8046: 8044: 8041: 8039: 8036: 8034: 8031: 8029: 8026: 8023: 8020: 8018: 8015: 8013: 8010: 8009: 8007: 8003: 8000: 7997: 7992: 7982: 7979: 7977: 7974: 7972: 7969: 7967: 7964: 7962: 7961:Niflumic acid 7959: 7957: 7954: 7952: 7949: 7947: 7944: 7942: 7939: 7937: 7934: 7932: 7929: 7927: 7924: 7923: 7921: 7917: 7911: 7908: 7905: 7901: 7898: 7896: 7893: 7891: 7888: 7885: 7881: 7878: 7877: 7875: 7871: 7868: 7865: 7860: 7850: 7849:Ruthenium red 7847: 7845: 7842: 7839: 7835: 7832: 7830: 7827: 7824: 7820: 7817: 7815: 7812: 7810: 7807: 7806: 7804: 7800: 7794: 7791: 7788: 7784: 7781: 7778: 7774: 7771: 7769: 7766: 7763: 7759: 7756: 7754: 7751: 7748: 7744: 7740: 7736: 7733: 7730: 7726: 7723: 7721: 7718: 7716: 7713: 7711: 7708: 7705: 7701: 7698: 7695: 7691: 7688: 7685: 7681: 7678: 7676: 7673: 7670: 7666: 7663: 7661: 7660:Methylglyoxal 7658: 7655: 7651: 7647: 7644: 7641: 7640: 7635: 7631: 7628: 7626: 7623: 7621: 7618: 7616: 7613: 7611: 7608: 7606: 7603: 7601: 7598: 7595: 7591: 7588: 7586: 7583: 7581: 7578: 7575: 7574: 7569: 7566: 7564: 7561: 7558: 7554: 7551: 7548: 7544: 7541: 7538: 7534: 7533:Cuminaldehyde 7531: 7529: 7526: 7524: 7521: 7518: 7514: 7511: 7508: 7504: 7501: 7498: 7494: 7491: 7488: 7484: 7481: 7479: 7476: 7474: 7471: 7469: 7466: 7463: 7459: 7455: 7451: 7447: 7444: 7441: 7437: 7434: 7432: 7429: 7426: 7422: 7418: 7414: 7411: 7409: 7406: 7404: 7401: 7399: 7396: 7394: 7391: 7389: 7386: 7385: 7383: 7379: 7376: 7373: 7368: 7364: 7361: 7351: 7346: 7344: 7339: 7337: 7332: 7331: 7328: 7312: 7310: 7307: 7306: 7304: 7301: 7298: 7295: 7293: 7290: 7289: 7285: 7279: 7276: 7274: 7271: 7269: 7266: 7264: 7261: 7259: 7256: 7254: 7251: 7249: 7246: 7244: 7241: 7239: 7236: 7234: 7231: 7229: 7226: 7224: 7221: 7219: 7216: 7214: 7211: 7210: 7208: 7204: 7198: 7195: 7193: 7192:Methocarbamol 7190: 7188: 7187:Mephenoxalone 7185: 7183: 7180: 7178: 7177:Chlorzoxazone 7175: 7173: 7170: 7169: 7167: 7165: 7161: 7151: 7148: 7147: 7145: 7143: 7139: 7133: 7130: 7128: 7125: 7123: 7120: 7113: 7112: 7108: 7107:amitriptyline 7104: 7101: 7099: 7096: 7094: 7091: 7088: 7084: 7080: 7077: 7075: 7072: 7070: 7069:Carbamazepine 7067: 7066: 7064: 7062: 7058: 7052: 7049: 7047: 7044: 7042: 7039: 7037: 7034: 7032: 7029: 7027: 7024: 7022: 7019: 7018: 7016: 7014: 7010: 7007: 7005: 6999: 6993: 6990: 6988: 6985: 6983: 6980: 6978: 6975: 6973: 6970: 6969: 6967: 6965: 6961: 6951: 6948: 6946: 6943: 6941: 6938: 6936: 6933: 6931: 6928: 6926: 6923: 6922: 6920: 6916: 6909: 6902: 6899: 6897: 6894: 6892: 6889: 6887: 6884: 6882: 6879: 6877: 6874: 6873: 6871: 6869: 6865: 6858: 6851: 6848: 6846: 6843: 6841: 6838: 6836: 6833: 6831: 6828: 6826: 6823: 6821: 6818: 6816: 6813: 6811: 6808: 6806: 6803: 6801: 6798: 6796: 6793: 6791: 6788: 6786: 6783: 6781: 6778: 6776: 6773: 6771: 6768: 6765: 6761: 6758: 6757: 6755: 6753: 6749: 6743: 6740: 6738: 6735: 6733: 6730: 6728: 6725: 6724: 6722: 6720: 6716: 6710: 6707: 6705: 6702: 6700: 6697: 6695: 6692: 6690: 6687: 6684: 6677: 6674: 6673: 6671: 6669: 6665: 6659: 6656: 6654: 6651: 6649: 6646: 6644: 6641: 6638: 6631: 6628: 6626: 6623: 6621: 6618: 6616: 6613: 6611: 6608: 6607: 6605: 6601: 6595: 6592: 6590: 6587: 6585: 6582: 6580: 6577: 6575: 6572: 6571: 6569: 6565: 6559: 6556: 6554: 6551: 6549: 6546: 6544: 6541: 6539: 6536: 6534: 6531: 6528: 6527:Dexketoprofen 6521: 6518: 6515: 6507: 6500: 6497: 6495: 6492: 6490: 6487: 6485: 6482: 6481: 6479: 6475: 6472: 6470: 6466: 6460: 6457: 6455: 6452: 6450: 6447: 6443: 6440: 6438: 6435: 6433: 6430: 6428: 6425: 6423: 6420: 6418: 6415: 6413: 6410: 6408: 6405: 6404: 6403: 6400: 6398: 6395: 6393: 6390: 6388: 6385: 6384: 6382: 6379: 6375: 6365: 6362: 6359: 6355: 6348: 6345: 6343: 6340: 6338: 6335: 6333: 6330: 6328: 6325: 6323: 6320: 6318: 6315: 6313: 6310: 6308: 6305: 6303: 6302:Phenoperidine 6300: 6298: 6295: 6293: 6290: 6288: 6285: 6283: 6280: 6278: 6275: 6273: 6270: 6268: 6265: 6263: 6260: 6258: 6255: 6253: 6250: 6248: 6245: 6242: 6238: 6235: 6233: 6232:Ethoheptazine 6230: 6228: 6225: 6223: 6220: 6218: 6215: 6213: 6210: 6208: 6205: 6203: 6200: 6198: 6195: 6193: 6190: 6188: 6185: 6183: 6180: 6179: 6177: 6173: 6167: 6164: 6162: 6159: 6157: 6154: 6151: 6147: 6143: 6139: 6135: 6128: 6125: 6123: 6120: 6118: 6115: 6113: 6110: 6108: 6105: 6103: 6100: 6098: 6095: 6093: 6092:Hydromorphone 6090: 6088: 6085: 6082: 6078: 6074: 6067: 6064: 6062: 6061:Ethylmorphine 6059: 6057: 6054: 6052: 6049: 6046: 6039: 6036: 6034: 6031: 6029: 6026: 6024: 6021: 6018: 6011: 6010:Buprenorphine 6008: 6006: 6003: 6001: 5998: 5997: 5995: 5993:Semisynthetic 5991: 5985: 5982: 5980: 5977: 5975: 5972: 5969: 5965: 5962: 5958: 5955: 5953: 5950: 5949: 5948: 5945: 5944: 5942: 5940: 5936: 5932: 5929: 5927: 5923: 5918: 5914: 5910: 5903: 5898: 5896: 5891: 5889: 5884: 5883: 5880: 5874: 5871: 5869: 5866: 5865: 5854: 5848: 5844: 5839: 5838: 5821: 5820:chili peppers 5816: 5815: 5808: 5804: 5800: 5793: 5789: 5785: 5781: 5777: 5771: 5768: 5764: 5760: 5757:(in French). 5756: 5752: 5745: 5742: 5739: 5738:pages 381–386 5736:..., vol. 6, 5735: 5731: 5727: 5724:(1819); (ii) 5723: 5719: 5713: 5710:(in German). 5709: 5704: 5703: 5702: 5701: 5697: 5694: 5690: 5686: 5685: 5678: 5674: 5673: 5666: 5662: 5658: 5657: 5651: 5647: 5646: 5640: 5639: 5635: 5631: 5616: 5612: 5607: 5602: 5597: 5592: 5588: 5584: 5580: 5573: 5565: 5561: 5557: 5553: 5548: 5543: 5539: 5535: 5531: 5524: 5516: 5512: 5507: 5502: 5498: 5494: 5490: 5486: 5482: 5475: 5467: 5463: 5459: 5455: 5451: 5447: 5443: 5439: 5435: 5431: 5424: 5416: 5412: 5407: 5402: 5397: 5392: 5388: 5384: 5380: 5378: 5374: 5365: 5350: 5349:npic.orst.edu 5346: 5340: 5332: 5328: 5323: 5318: 5314: 5310: 5306: 5302: 5298: 5294: 5290: 5283: 5275: 5271: 5266: 5261: 5256: 5251: 5247: 5243: 5239: 5237: 5228: 5220: 5216: 5211: 5206: 5202: 5198: 5194: 5190: 5186: 5179: 5164: 5160: 5154: 5146: 5142: 5137: 5132: 5127: 5122: 5118: 5114: 5110: 5103: 5095: 5091: 5086: 5081: 5076: 5071: 5067: 5063: 5059: 5057: 5048: 5040: 5036: 5031: 5026: 5021: 5016: 5012: 5008: 5004: 5000: 4996: 4989: 4981: 4977: 4973: 4969: 4964: 4959: 4955: 4951: 4947: 4940: 4932: 4928: 4924: 4920: 4916: 4912: 4905: 4897: 4893: 4889: 4885: 4881: 4877: 4869: 4861: 4859:9781441972996 4855: 4851: 4847: 4845: 4836: 4827: 4822: 4818: 4814: 4810: 4808: 4804: 4795: 4787: 4783: 4779: 4775: 4768: 4766: 4764: 4755: 4751: 4746: 4741: 4737: 4733: 4729: 4722: 4714: 4710: 4706: 4702: 4701:J Am Chem Soc 4698: 4691: 4683: 4679: 4675: 4671: 4667: 4663: 4659: 4655: 4651: 4644: 4636: 4632: 4628: 4624: 4620: 4616: 4609: 4601: 4597: 4593: 4589: 4585: 4581: 4577: 4570: 4562: 4558: 4554: 4550: 4543: 4535: 4531: 4527: 4523: 4516: 4508: 4504: 4500: 4496: 4492: 4488: 4481: 4479: 4477: 4475: 4465: 4457: 4453: 4449: 4445: 4441: 4434: 4426: 4422: 4418: 4411: 4403: 4396: 4388: 4384: 4380: 4376: 4372: 4368: 4364: 4357: 4349: 4345: 4341: 4334: 4326: 4322: 4315: 4307: 4303: 4299: 4292: 4284: 4280: 4276: 4269: 4260: 4255: 4251: 4247: 4243: 4239: 4232: 4223: 4218: 4214: 4210: 4206: 4202: 4195: 4187: 4183: 4179: 4175: 4168: 4160: 4156: 4152: 4148: 4144: 4137: 4129: 4125: 4121: 4118:(in German). 4117: 4113: 4106: 4098: 4094: 4090: 4087:(in German). 4086: 4082: 4075: 4066: 4060: 4056: 4049: 4041: 4037: 4032: 4027: 4023: 4019: 4015: 4011: 4007: 4000: 3990: 3985: 3981: 3977: 3972: 3969: 3966: 3962: 3958: 3954: 3950: 3946: 3942: 3938: 3936: 3927: 3923: 3919: 3914: 3910: 3906: 3901: 3900: 3896: 3888: 3884: 3877: 3869: 3865: 3858: 3842: 3836: 3828: 3824: 3820: 3816: 3811: 3810:10.1038/39807 3806: 3802: 3798: 3794: 3790: 3786: 3779: 3771: 3767: 3763: 3759: 3752: 3736: 3730: 3728: 3726: 3724: 3722: 3713: 3709: 3704: 3699: 3694: 3689: 3685: 3681: 3677: 3670: 3662: 3661: 3656: 3650: 3642: 3641: 3636: 3630: 3622: 3618: 3614: 3610: 3606: 3602: 3598: 3594: 3587: 3579: 3575: 3571: 3567: 3563: 3559: 3555: 3551: 3544: 3536: 3532: 3528: 3524: 3520: 3516: 3512: 3508: 3504: 3497: 3489: 3485: 3478: 3470: 3464: 3460: 3453: 3445: 3441: 3437: 3433: 3426: 3418: 3414: 3410: 3406: 3401: 3396: 3392: 3388: 3384: 3377: 3358: 3354: 3348: 3346: 3344: 3327: 3323: 3317: 3315: 3306: 3302: 3298: 3294: 3290: 3286: 3282: 3278: 3274: 3270: 3263: 3247: 3241: 3233: 3229: 3225: 3221: 3217: 3213: 3206: 3187: 3180: 3174: 3172: 3163: 3159: 3154: 3149: 3145: 3141: 3137: 3130: 3122: 3118: 3114: 3110: 3106: 3102: 3098: 3094: 3087: 3079: 3075: 3071: 3067: 3063: 3059: 3052: 3044: 3040: 3036: 3032: 3027: 3022: 3018: 3014: 3010: 3003: 2984: 2980: 2976: 2971: 2966: 2962: 2961:10044/1/49554 2958: 2954: 2950: 2946: 2942: 2935: 2928: 2912: 2905: 2889: 2887: 2882: 2876: 2866: 2859: 2855: 2854: 2843: 2841: 2835: 2829: 2813: 2809: 2803: 2795: 2791: 2786: 2781: 2776: 2771: 2767: 2763: 2759: 2752: 2750: 2748: 2746: 2744: 2735: 2731: 2726: 2721: 2717: 2713: 2709: 2705: 2701: 2694: 2692: 2676: 2672: 2665: 2663: 2661: 2659: 2650: 2646: 2642: 2638: 2634: 2630: 2626: 2622: 2618: 2614: 2607: 2599: 2595: 2590: 2585: 2580: 2575: 2571: 2567: 2563: 2559: 2555: 2548: 2540: 2536: 2532: 2528: 2524: 2520: 2516: 2512: 2505: 2503: 2501: 2485:on 4 May 2007 2484: 2480: 2474: 2472: 2463: 2459: 2453: 2445: 2441: 2437: 2433: 2429: 2425: 2417: 2415: 2398: 2396: 2390: 2384: 2368: 2364: 2358: 2342: 2336: 2334: 2332: 2330: 2328: 2326: 2324: 2307: 2301: 2297: 2287: 2284: 2282: 2278: 2275: 2272: 2268: 2264: 2260: 2257: 2255: 2251: 2248: 2245: 2242: 2239: 2235: 2231: 2228:, the active 2227: 2224: 2223: 2217: 2215: 2204: 2201: 2192: 2190: 2180: 2177: 2172: 2161: 2159: 2155: 2151: 2147: 2146: 2141: 2137: 2136:genetic drift 2133: 2129: 2125: 2115: 2112: 2108: 2107: 2101: 2099: 2095: 2091: 2090:vanillylamine 2086: 2084: 2080: 2077: 2073: 2069: 2066: 2062: 2058: 2057: 2046: 2044: 2040: 2036: 2032: 2017: 2009: 2001: 1995:Chili peppers 1993: 1979: 1975: 1972: 1970: 1967: 1965: 1962: 1961: 1957: 1953: 1950: 1947: 1944: 1942: 1939: 1938: 1934: 1930: 1927: 1924: 1921: 1919: 1918:Homocapsaicin 1916: 1915: 1911: 1907: 1904: 1901: 1898: 1896: 1893: 1892: 1888: 1884: 1881: 1878: 1875: 1873: 1870: 1869: 1865: 1861: 1858: 1855: 1852: 1849: 1848: 1844: 1840: 1837: 1830: 1825: 1822: 1821: 1818: 1816: 1812: 1807: 1805: 1801: 1796: 1792: 1785:Capsaicinoids 1782: 1780: 1776: 1772: 1768: 1758: 1756: 1752: 1747: 1744: 1740: 1736: 1735:cell membrane 1732: 1728: 1724: 1720: 1716: 1712: 1702: 1700: 1690: 1688: 1678: 1676: 1675:carbohydrates 1672: 1671:meta-analysis 1668: 1664: 1654: 1652: 1648: 1644: 1639: 1631: 1629: 1628:blepharospasm 1625: 1619: 1617: 1598: 1596: 1592: 1582: 1579: 1576: 1571: 1569: 1564: 1562: 1558: 1548: 1546: 1542: 1538: 1533: 1531: 1527: 1523: 1519: 1514: 1512: 1508: 1503: 1499: 1495: 1491: 1487: 1483: 1479: 1476: 1475:post-herpetic 1472: 1467: 1465: 1461: 1457: 1453: 1449: 1445: 1441: 1431: 1429: 1427: 1423: 1419: 1415: 1411: 1407: 1406:Tabasco sauce 1403: 1399: 1394: 1392: 1388: 1384: 1380: 1376: 1368: 1364: 1359: 1344: 1342: 1340: 1335: 1331: 1326: 1324: 1323: 1318: 1314: 1310: 1305: 1301: 1298:The seeds of 1296: 1294: 1290: 1289: 1284: 1274: 1272: 1268: 1264: 1260: 1256: 1252: 1251: 1246: 1245:chili peppers 1240: 1199: 1163: 1161: 1155: 1146: 1144: 1140: 1134: 1130: 1125: 1114: 1107: 1102: 1085: 1079: 1076: 1073: 1070: 1069: 1062: 1055: 1048: 1024: 1021: 1020: 1016: 1015: 957: 954: 950: 949: 931: 928: 924: 923: 920: 917: 914: 910: 909: 905: 900: 895: 890: 886: 883: 879: 878: 874: 872: 867: 862: 856: 846: 845: 843: 841: 838: 837: 830: 825: 816: 815: 813: 811: 808: 807: 802: 797: 792: 787: 784: 781: 777: 776: 773:Pharmacology 771: 767: 764: 760: 759: 754: 750: 743: 740: 739: 731:10 mm Hg 725: 723: 720: 719: 713: 709: 705: 698: 696: 692: 688: 687: 685: 683: 680: 679: 667: 664: 660: 659: 651: 649: 648:Boiling point 646: 645: 641: 639: 638:Melting point 636: 635: 631: 629: 626: 625: 621: 618: 617: 610: 608: 605: 604: 580: 577: 573: 572: 567: 558: 557: 554: 547: 533: 523: 522: 519: 512: 504: 500: 499:DTXSID9020241 496: 495: 493: 483: 479: 478: 471: 467: 466: 464: 462: 459: 458: 451: 447: 446: 444: 438: 434: 433: 426: 422: 421: 419: 417: 414: 413: 406: 402: 401: 399: 396: 392: 391: 384: 383: 381: 379: 374: 373: 369: 365: 362: 360: 358:ECHA InfoCard 355: 354: 347: 343: 342: 340: 338: 335: 334: 327: 323: 322: 320: 318: 315: 314: 307: 303: 302: 300: 298: 295: 294: 287: 283: 282: 280: 278: 275: 274: 270: 267: 263: 262: 255: 251: 250: 248: 244: 239: 238: 231: 227: 226: 224: 221: 217: 216: 211: 200: 194: 190: 186:-6-nonenamide 185: 181: 175: 171: 164: 158: 154: 148: 144: 139: 98: 63: 60: 59: 54: 50: 45: 41: 36: 30: 19: 18:Capsaicinoids 14833:Pepper spray 14807: 14762:Pepper jelly 14693:Filfel chuma 14683:Chili thread 14678:Chili powder 14593: 14493:Bhut jolokia 14467: 14437: 14215: 14154: 14153: 14118:Valnoctamide 14113:Tucidinostat 14098:Sulforaphane 14043:Parthenolide 14038:Panobinostat 14028:Mocetinostat 14003:Fimepinostat 13983:Citarinostat 13977: 13869: 13849: 13744:Ferulic acid 13709:Caffeic acid 13682:Ellagic acid 13422: 13413:isocoumarins 13386:Kavalactones 13328:Tannin uses 13255:Tetrafucol A 13235:Diphlorethol 13220:6,6'-Bieckol 13215:8,8′-Bieckol 13137:Gallotannins 13102:Casuarictins 13082:Punicalagins 13007:Curcuminoids 12952:Matairesinol 12853: 12758:Apigeninidin 12703:Aromadendrin 12610:Flavan-4-ols 12581:Flavan-3-ols 12318:Benzenediols 12253: 12097:Chlorophylls 12085:Vulgaxanthin 12075:Betaxanthins 11994:Polysulfides 11977:Thiocyanates 11955:Sulforaphane 11884: 11864: 11759:Ferulic acid 11724:Caffeic acid 11697:Ellagic acid 11437: 11428:isocoumarins 11401:Kavalactones 11343:Tannin uses 11270:Tetrafucol A 11250:Diphlorethol 11235:6,6'-Bieckol 11230:8,8′-Bieckol 11152:Gallotannins 11117:Casuarictins 11097:Punicalagins 11022:Curcuminoids 10967:Matairesinol 10868: 10773:Apigeninidin 10718:Aromadendrin 10625:Flavan-4-ols 10596:Flavan-3-ols 10333:Benzenediols 10202:Gutta-balatá 10198:Gutta percha 10136:Xanthophylls 10116:Neurosporene 10035:Moronic acid 10025:Ursolic acid 9968:Testosterone 9951:Stigmasterol 9936:Cycloartenol 9923:Phytosterols 9865:Pimaric acid 9835:Abietic acid 9786:Manoyl oxide 9761:Salvinorin A 9751: 9691:Diterpenoids 9555:Thujaplicins 9480:(2,modified) 9420:Phellandrene 9364:Monoterpenes 9293: 9289: 9282:Basic forms: 9170: 9169: 9010:Cannabigerol 8981: 8934: 8876: 8864: 8826:black pepper 8786:chili pepper 8719:chili pepper 8709:chili pepper 8700:Hepoxilin B3 8695:Hepoxilin A3 8666: 8638:chili pepper 8596:chili pepper 8591: 8537: 8400: 8259: 8186:Clotrimazole 8127: 8111: 8063:Frescolat ML 7971:Progesterone 7880:Adhyperforin 7793:WIN 55,212-2 7786: 7637: 7605:Hepoxilin B3 7600:Hepoxilin A3 7571: 7503:Cannabigerol 7232: 7197:Orphenadrine 7172:Carisoprodol 7164:Myorelaxants 7114: 6964:Cannabinoids 6930:Floctafenine 6835:Salicylamide 6514:+paracetamol 6506:Dexibuprofen 6494:Flurbiprofen 6484:Benoxaprofen 6459:Propacetamol 6449:Parapropamol 6417:+hydrocodone 6358:+paracetamol 6327:Remifentanil 6317:Proheptazine 6247:Ketobemidone 6187:Alphaprodine 6134:+paracetamol 6122:Nicomorphine 6117:Nicodicodine 6073:+paracetamol 6045:+paracetamol 6028:Desomorphine 5957:+paracetamol 5845:. 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Retrieved 2300: 2281:black pepper 2210: 2198: 2186: 2167: 2149: 2143: 2131: 2127: 2123: 2121: 2104: 2102: 2087: 2075: 2071: 2065:interlocular 2054: 2052: 2042: 2034: 2027: 1987:Biosynthesis 1814: 1808: 1797: 1794: 1779:gastric acid 1764: 1748: 1708: 1696: 1687:peptic ulcer 1684: 1681:Peptic ulcer 1660: 1640: 1637: 1620: 1609: 1588: 1580: 1574: 1572: 1565: 1557:pepper spray 1554: 1534: 1515: 1489: 1468: 1464:rubefacients 1437: 1430: 1408:and Mexican 1398:chili pepper 1395: 1383:chili powder 1372: 1337: 1330:vanillotoxin 1327: 1320: 1299: 1297: 1286: 1280: 1248: 1159: 1157: 1153: 1152: 1018: 918: 870: 840:Legal status 810:License data 306:ChEMBL294199 213:Identifiers 198: 192: 188: 183: 179: 173: 169: 166:Other names 156: 152: 29: 14747:Chili sauce 14554:Naga Morich 14423:Siling haba 14383:Peperoncino 14306:Friggitello 14246:Black Pearl 14063:Resminostat 14058:Quisinostat 14053:Pracinostat 14033:Niacinamide 14023:Martinostat 13948:Abexinostat 13829:Oleocanthal 13646:Norbergenin 13641:Tannic acid 13636:Gallic acid 13430:Polyphenols 13403:Xanthonoids 13380:Chalconoids 13230:Eckstolonol 13127:Terflavin B 13092:Vescalagins 13087:Castalagins 12992:Piceatannol 12982:Resveratrol 12972:Stilbenoids 12962:Pinoresinol 12897:Castavinols 12739:Delphinidin 12690:Flavanonols 12680:Eriodictyol 12507:Isoflavones 12389:polyphenols 12353:Polyphenols 12208:Beta-glucan 12138:Oxalic acid 12131:Quinic acid 12126:Phytic acid 12063:Betacyanins 11844:Oleocanthal 11661:Norbergenin 11656:Tannic acid 11651:Gallic acid 11445:Polyphenols 11418:Xanthonoids 11395:Chalconoids 11245:Eckstolonol 11142:Terflavin B 11107:Vescalagins 11102:Castalagins 11007:Piceatannol 10997:Resveratrol 10987:Stilbenoids 10977:Pinoresinol 10912:Castavinols 10754:Delphinidin 10705:Flavanonols 10695:Eriodictyol 10522:Isoflavones 10404:polyphenols 10368:Polyphenols 10170:Rubixanthin 10160:Astaxanthin 10121:Phytofluene 10073:Carotenoids 9963:Cholesterol 9958:Tocopherols 9928:Campesterol 9827:Resin acids 9812:Gibberellin 9807:Aphidicolin 9800:Tetracyclic 9675:Longifolene 9639:Artemisinin 9616:Umbellulone 9504:Citronellol 9494:Citronellal 9145:Tivanisiran 9050:Capsazepine 8962:Zucapsaicin 8830:long pepper 8796:Pacific yew 8685:GSK1016790A 8572:Cannabidiol 8558:camphorweed 8246:RQ-00203078 8241:PF-05105679 8181:Capsazepine 7946:GSK2293017A 7910:Substance P 7895:GSK1702934A 7844:PF-04745637 7783:Umbellulone 7704:Pacific yew 7690:Oleocanthal 7669:wintergreen 7630:Ligustilide 7493:Cannabidiol 7458:horseradish 7299:from market 7243:Frunevetmab 7223:Bedinvetmab 7132:PF-05089771 7041:Mirogabalin 7002:Ion channel 6972:Cannabidiol 6925:Benzydamine 6868:Pyrazolones 6850:Wintergreen 6800:Ethenzamide 6795:Dipyrocetyl 6752:Salicylates 6694:Lumiracoxib 6630:Indometacin 6558:Zaltoprofen 6477:Propionates 6387:Acetanilide 6378:Paracetamol 6312:Piritramide 6297:Phenazocine 6292:Phenadoxone 6282:Pentazocine 6277:Oliceridine 6272:Norpipanone 6241:+fluanisone 6222:Dimenoxadol 6202:Carfentanil 6197:Bezitramide 6192:Anileridine 6161:Papaveretum 6156:Oxymorphone 6150:+naltrexone 6112:Nicocodeine 6097:Levorphanol 6066:Hydrocodone 6023:Butorphanol 5968:+naltrexone 5667:appear in: 5589:(7): 1286. 5534:HortScience 5299:(1): 9963. 5068:(2): 1046. 4780:: 442–446. 4215:: 923–927. 3941:The Analyst 3735:"Capsaicin" 3556:: 183–188. 3195:13 November 2403:22 February 2373:22 February 2341:"Capsaicin" 2306:"Capsaicin" 2244:Capsazepine 2200:Granivorous 2158:granivorous 1882:16,000,000 1859:16,000,000 1842:heat units 1494:therapeutic 1486:transdermal 1317:anti-fungal 1309:molar teeth 1267:hydrophobic 913:Signal word 768:Monoclinic 619:Appearance 569:Properties 364:100.006.337 201:)-Capsaicin 14908:Categories 14818:Chilympiad 14730:and sauces 14728:Condiments 14713:Peppersoup 14688:Ema datshi 14569:Red Savina 14559:Naga Viper 14453:Lemon drop 14428:Urfa biber 14341:New Mexico 14261:Cheongyang 14241:Bird's eye 14138:Valpromide 14103:Trapoxin B 14068:Romidepsin 14008:Givinostat 13998:Entinostat 13968:Belinostat 13834:Oleuropein 13772:tryptophan 13661:Theogallin 13528:Glycosides 13405:(C6-C1-C6) 13382:(C6-C3-C6) 13371:(C6-C7-C6) 13332:Enological 13112:Punicalins 13107:Grandinins 12997:Pinosylvin 12975:(C6-C2-C6) 12790:Leptosidin 12785:Aureusidin 12675:Naringenin 12670:Hesperidin 12662:Flavanones 12628:Luteoforol 12496:Kaempferol 12443:Flavonoids 12435:flavonoids 12400:(C6-C3-C6) 12397:Flavonoids 12343:Dillapiole 12153:Malic acid 11849:Oleuropein 11787:tryptophan 11676:Theogallin 11543:Glycosides 11420:(C6-C1-C6) 11397:(C6-C3-C6) 11386:(C6-C7-C6) 11347:Enological 11127:Punicalins 11122:Grandinins 11012:Pinosylvin 10990:(C6-C2-C6) 10805:Leptosidin 10800:Aureusidin 10690:Naringenin 10685:Hesperidin 10677:Flavanones 10643:Luteoforol 10511:Kaempferol 10458:Flavonoids 10450:flavonoids 10415:(C6-C3-C6) 10412:Flavonoids 10358:Dillapiole 10155:Zeaxanthin 9999:Lanosterol 9946:Sitosterol 9941:Sitostanol 9817:Paclitaxel 9724:Monocyclic 9611:Ascaridole 9606:Eucalyptol 9559:Hinokitiol 9533:Monocyclic 9403:Monocyclic 9270:terpenoids 9228:Terpenoids 9040:Cannabinol 8940:pooissonii 8931:Tinyatoxin 8882:pooissonii 8846:Probenecid 8836:Polygodial 8792:Paclitaxel 8776:PAVA spray 8663:Evodiamine 8614:pepperwort 8529:Anandamide 8496:α-Sanshool 8444:Activators 8397:Triptolide 8390:Activators 8302:Activators 8278:TRPM4-IN-5 8196:Elismetrep 8124:stevioside 8052:eucalyptus 8048:Eucalyptol 8012:ADP-ribose 8005:Activators 7941:GSK417651A 7900:Hyperforin 7873:Activators 7753:Tear gases 7725:Polygodial 7715:PF-4840154 7700:Paclitaxel 7568:Dicentrine 7478:Bradykinin 7413:α-Sanshool 7381:Activators 7363:modulators 7273:Rimazolium 7268:Proglumide 7213:Analgecine 7150:Flupirtine 7093:Mexiletine 7074:Lacosamide 7051:Ziconotide 7046:Pregabalin 7036:Leconotide 7026:Gabapentin 7004:modulators 6987:Nabiximols 6950:Proquazone 6945:Nimesulide 6940:Nabumetone 6891:Nifenazone 6805:Guacetisal 6790:Diflunisal 6775:Benorylate 6709:Valdecoxib 6689:Etoricoxib 6620:Diclofenac 6610:Acemetacin 6579:Lornoxicam 6533:Loxoprofen 6520:Ketoprofen 6489:Fenoprofen 6454:Phenacetin 6432:+oxycodone 6422:+ibuprofen 6354:+celecoxib 6337:Tapentadol 6332:Sufentanil 6307:Piminodine 6257:Meptazinol 6252:Lofentanil 6227:Dipipanone 6182:Alfentanil 6142:+ibuprofen 6107:Nalbuphine 6077:+ibuprofen 5909:Analgesics 5751:Ranunculus 5720:, vol. 6, 5389:(5): 132. 5248:(7): 795. 4064:1888483024 3991:: 485–488. 3928:(315): 21. 3911:: 941–947. 2768:(7): 844. 2710:: 96–105. 2292:References 2176:ergosterol 2132:Solanaceae 2128:Solanaceae 1973:9,200,000 1964:Nonivamide 1951:8,600,000 1928:8,600,000 1905:9,100,000 1791:Capsinoids 1789:See also: 1711:nociceptor 1647:surfactant 1480:caused by 1473:, such as 1471:neuropathy 1422:endorphins 1418:chiliheads 1402:hot sauces 1135:Above peak 882:Pictograms 756:Structure 735:25 °C 682:Solubility 607:Molar mass 470:S07O44R1ZM 395:IUPHAR/BPS 317:ChemSpider 286:CHEBI:3374 241:3D model ( 220:CAS Number 191:-8-Methyl- 182:-vanillyl- 33:Capsaicin 14808:Capsaicin 14752:Hot sauce 14742:Chili oil 14708:Nam phrik 14698:Gochujang 14663:Chili dog 14614:Malagueta 14488:Ají dulce 14286:Espelette 14271:Cubanelle 14266:Chiltepin 14207:Cultivars 14155:See also: 14073:Scriptaid 13978:Capsaicin 13850:Capsaicin 13787:thyroxine 13777:histidine 13502:Aglycones 13409:Coumarins 13265:Bifuhalol 13192:Flavolans 13117:Roburin A 13097:Castalins 12930:Silymarin 12840:Phloretin 12809:Chalcones 12800:Chalcones 12698:Taxifolin 12615:flavanols 12586:flavanols 12519:Genistein 12492:Quercetin 12484:Flavonols 12433:Types of 12387:Types of 12338:Carvacrol 12300:Types of 12055:Betalains 11865:Capsaicin 11802:thyroxine 11792:histidine 11517:Aglycones 11424:Coumarins 11280:Bifuhalol 11207:Flavolans 11132:Roburin A 11112:Castalins 10945:Silymarin 10855:Phloretin 10824:Chalcones 10815:Chalcones 10713:Taxifolin 10630:flavanols 10601:flavanols 10534:Genistein 10507:Quercetin 10499:Flavonols 10448:Types of 10402:Types of 10353:Carvacrol 10315:Types of 10227:Synthesis 10083:Carotenes 9978:Ecdysones 9782:Forskolin 9770:Tricyclic 9757:Epimanool 9682:Nootkatin 9679:Muurolene 9671:Juniperol 9663:Chanootin 9644:Bisabolol 9575:Carvacrol 9415:Terpinene 9317:(4 rings) 9264:Types of 9218:Types of 9171:See also: 9155:TRPV3-74a 9140:SB-705498 9135:SB-366791 9085:Lanthanum 9080:HC-067047 9000:Asivatrep 8861:Rutamarin 8725:Incensole 8675:Gingerols 8644:Estradiol 8620:, others) 8602:Carvacrol 8592:Capsaicin 8486:13-oxoODE 8476:12S-HpETE 8456:5',6'-EET 8256:Rutamarin 8155:Thio-BCTC 8108:Rutamarin 8038:Coolact P 7829:HC-030031 7694:olive oil 7590:Gingerols 7403:12S-HpETE 7309:Phase III 7297:Withdrawn 7278:Tanezumab 7238:Clonidine 7233:Capsaicin 7087:lidocaine 6935:Glafenine 6896:Phenazone 6840:Salsalate 6770:Aloxiprin 6719:Fenamates 6704:Rofecoxib 6699:Parecoxib 6683:+tramadol 6676:Celecoxib 6658:Zomepirac 6643:Ketorolac 6615:Bromfenac 6594:Tenoxicam 6589:Piroxicam 6584:Meloxicam 6543:Oxaprozin 6499:Ibuprofen 6442:+tramadol 6397:Butacetin 6262:Methadone 6175:Synthetic 6146:+naloxone 6127:Oxycodone 6056:Etorphine 6017:+naloxone 5984:Paregoric 5556:0018-5345 5430:Oecologia 5119:(2): 22. 4980:164335348 4972:2352-6181 4654:Plant Sci 4629:: 23–32. 4621:fruits". 4578:fruits". 4174:Chem. Ber 3920:fruits". 3417:208154058 2917:5 January 2894:19 August 2848:19 August 2818:5 January 2762:Molecules 2214:pericarps 2189:dysplasia 2160:mammals. 2118:Evolution 2092:from the 2061:alkaloids 1850:Capsaicin 1833:relative 1817:species. 1719:vanilloid 1653:with it. 1518:psoriasis 1478:neuralgia 1456:arthritis 1440:analgesic 1426:analgesic 1336:species ( 1334:tarantula 1158:8-methyl- 1154:Capsaicin 1127:Capsaicin 999:P332+P313 979:P302+P352 975:P301+P312 971:P301+P310 873:labelling 712:petroleum 385:206-969-8 377:EC Number 203:Capsicine 178:8-Methyl- 14898:Medicine 14861:Category 14801:See also 14792:XO sauce 14777:Sriracha 14772:Shichimi 14757:Kōrēgusu 14718:Piperade 14564:Pepper X 14534:Infinity 14524:Habanero 14458:Peppadew 14418:Shishito 14403:Piquillo 14398:Pimiento 14326:Jalapeño 14311:Guajillo 14281:Dundicut 14251:Cascabel 14018:Kevetrin 13988:Curcumin 13963:Apicidin 13855:Gingerol 13782:tyrosine 13739:Coumarin 13677:Vanillin 13616:Bergenin 13337:Drilling 13260:Trifucol 13013:Curcumin 12941:((C6-C3) 12735:Cyanidin 12624:Apiforol 12595:Catechin 12515:Daidzein 12469:Apigenin 12461:Flavones 12333:Carnosol 12218:Lentinan 12196:Pentoses 12038:Piperine 11989:Sulfides 11972:Nitriles 11930:Sinigrin 11870:Gingerol 11797:tyrosine 11754:Coumarin 11692:Vanillin 11631:Bergenin 11352:Drilling 11275:Trifucol 11028:Curcumin 10956:((C6-C3) 10750:Cyanidin 10639:Apiforol 10610:Catechin 10530:Daidzein 10484:Apigenin 10476:Flavones 10348:Carnosol 10126:Phytoene 10111:Lycopene 10012:Squalane 10004:Saponins 9915:Steroids 9777:Cembrene 9754:-Abienol 9745:Bicyclic 9649:Cadinene 9584:Bicyclic 9550:p-Cymene 9524:Linalool 9509:Geraniol 9460:Sabinene 9450:Camphene 9429:Bicyclic 9410:Limonene 9394:Myrcenes 9335:Isoprene 9315:Steroids 9306:Iridoids 9274:isoprene 9266:terpenes 9105:NGD-8243 9090:Mavatrep 9075:GRC-6211 9044:cannabis 9034:cannabis 9024:cannabis 9014:cannabis 8995:AMG-9810 8971:Blockers 8952:Vanillin 8947:Tramadol 8911:cannabis 8889:Shogaols 8822:Piperine 8586:cannabis 8576:cannabis 8554:rosemary 8471:12S-HETE 8466:9-oxoODE 8413:Blockers 8363:PI(4,5)P 8351:Blockers 8329:PI(3,5)P 8236:Ononetin 8221:Nicotine 8169:Blockers 8145:fructose 8137:tastants 8083:Linalool 8068:Geraniol 8028:CIM-0216 7919:Blockers 7834:Nicotine 7809:A-967079 7802:Blockers 7762:cannabis 7735:Shogaols 7680:Nicotine 7646:Linalool 7585:Formalin 7547:turmeric 7543:Curcumin 7517:cinnamon 7507:cannabis 7497:cannabis 7487:cannabis 7473:ASP-7663 7431:Acrolein 7248:Ketamine 7127:Funapide 7122:DSP-2230 6982:Nabilone 6977:Cannabis 6881:Ampyrone 6653:Tolmetin 6648:Sulindac 6625:Etodolac 6603:Acetates 6574:Isoxicam 6548:Suprofen 6538:Naproxen 6412:+codeine 6347:Tramadol 6342:Tilidine 6322:Propiram 6237:Fentanyl 6217:Dezocine 6166:Thebacon 6138:+aspirin 6081:+aspirin 5979:Laudanum 5964:Morphine 5952:+aspirin 5814:Capsicum 5763:122- 131 5730:page 146 5714:: 63–73. 5615:34202853 5564:86280396 5515:22189403 5466:10892233 5458:16896774 5415:31064092 5331:32561812 5274:32679672 5219:28044278 5145:29371540 5094:36674560 5039:18695236 4931:18489121 4896:16277419 4844:Capsicum 4754:15918882 4699:. III". 4697:Capsicum 4682:86735106 4650:Capsicum 4619:Capsicum 4615:Capsicum 4440:Capsicum 4387:32414315 4342:)]. 4308:: 507ff. 4040:20776886 3982:: 24–25. 3935:Capsicum 3918:Capsicum 3712:22264348 3621:40023195 3613:16621751 3578:30252935 3570:24246368 3550:Appetite 3527:16840650 3409:17365137 3305:19121573 3297:17090499 3232:12974352 3162:33840333 3121:24484878 3113:21128913 3043:29307090 2979:28085183 2794:27367653 2734:25307998 2680:16 March 2641:17093448 2598:18695236 2531:11473305 2367:DailyMed 2277:Piperine 2220:See also 2150:Capsicum 2145:Capsicum 2124:Capsicum 2106:Capsicum 2056:Capsicum 1839:Scoville 1831:Typical 1815:Capsicum 1743:impulses 1723:receptor 1667:pungency 1651:emulsion 1537:diabetes 1526:pruritus 1482:shingles 1414:euphoric 1404:such as 1381:such as 1358:Pungency 1322:Fusarium 1300:Capsicum 1288:Capsicum 1255:irritant 1250:Capsicum 1019:NFPA 704 864:Hazards 780:ATC code 337:DrugBank 271:2816484 230:404-86-4 205:Capsicin 14871:Commons 14703:Harissa 14653:Adobada 14609:Kambuzi 14549:Nagabon 14519:Fatalii 14413:Serrano 14408:Poblano 14378:Pasilla 14351:Chimayo 14346:Big Jim 14301:Florina 14256:Cayenne 13819:Tyrosol 13399:(C6-C3) 13393:(C6-C4) 13347:Tanning 13240:Difucol 13225:Dieckol 13057:tannins 13021:Tannins 12938:Lignans 12823:, et.c. 12777:Aurones 12764:, et.c. 12741:, et.c. 12705:, et.c. 12653:, et.c. 12630:, et.c. 12601:, et.c. 12556:Flavans 12498:, et.c. 12475:, et.c. 12473:Chrysin 12230:Inulins 12225:Fructan 12191:Hexoses 12068:Betanin 12023:Allicin 12008:Indoles 11834:Tyrosol 11414:(C6-C3) 11408:(C6-C4) 11362:Tanning 11255:Difucol 11240:Dieckol 11072:tannins 11036:Tannins 10953:Lignans 10838:, et.c. 10792:Aurones 10779:, et.c. 10756:, et.c. 10720:, et.c. 10668:, et.c. 10645:, et.c. 10616:, et.c. 10571:Flavans 10513:, et.c. 10490:, et.c. 10488:Chrysin 10264:(DMAPP) 9994:Betulin 9792:Pimarol 9789:Pimaral 9736:Retinal 9731:Retinol 9700:Acyclic 9659:Cedrene 9654:Cadinol 9596:Borneol 9591:Camphor 9545:Menthol 9519:Halomon 9487:Acyclic 9455:Thujene 9389:Ocimene 9382:Acyclic 9125:RN-9893 9120:RN-1734 8990:AMG-517 8956:vanilla 8925:oregano 8897:Sichuan 8875:(RTX) ( 8851:Protons 8814:(e.g., 8747:Menthol 8729:incense 8649:Eugenol 8606:oregano 8546:Camphor 8514:Allicin 8504:Sichuan 8491:20-HETE 8481:13-HODE 8324:ML2-SA1 8225:tobacco 8176:AMG-333 8149:sucrose 8141:glucose 8139:(e.g., 8122:(e.g., 8088:Menthol 8022:Calcium 7838:tobacco 7814:AM-0902 7743:Sichuan 7684:tobacco 7573:Lindera 7450:mustard 7436:Allicin 7421:Sichuan 7398:4,5-EET 7360:channel 7253:Menthol 7228:Camphor 7105:(e.g., 7098:Nefopam 7083:cocaine 7081:(e.g., 6830:Salicin 6567:Oxicams 6392:Bucetin 6364:Viminol 6102:Metopon 5947:Codeine 5935:Opiates 5926:Opioids 5788:173–174 5753:]. 5606:8309139 5506:3311884 5438:Bibcode 5406:6572632 5383:Insects 5322:7305228 5301:Bibcode 5265:7397035 5210:5326624 5136:5715925 5085:9860720 5030:2575311 5007:Bibcode 4662:Bibcode 4588:Bibcode 4507:5687710 4419:: 442. 4281:]. 4252:: 251. 4031:2521090 3949:Bibcode 3937:fruits" 3827:7970319 3819:9349813 3797:Bibcode 3703:3284873 3660:AP News 3535:7529851 3444:9251180 3366:13 July 3332:1 April 3277:Bibcode 3078:7688774 3035:1711752 2970:6464756 2785:6273101 2725:4267963 2649:4387600 2621:Bibcode 2589:2575311 2566:Bibcode 2539:4389051 2444:2039598 2230:piquant 2226:Allicin 2154:fitness 2024:History 1835:amount 1827:Abbrev. 1804:pungent 1761:History 1731:cations 1643:caseins 1490:Qutenza 1488:patch ( 1460:sprains 1452:muscles 1387:paprika 1271:pungent 1106:what is 1104: ( 826::  798: ( 796:N01BX04 794:) 788: ( 786:M02AB01 751:280 nm 695:benzene 674:  612:305.418 450:1548943 437:PubChem 346:DB06774 326:1265957 14884:Portal 14838:Ristra 14478:Adjuma 14388:Pequin 14373:Padrón 14361:Sandia 14356:Fresno 14336:Medusa 14331:Korean 14231:Banana 14226:Aleppo 13843:Others 13797:L-DOPA 13362:Others 12817:Butein 12564:Flavan 12523:Orobol 12328:Apiole 12242:Pectin 12237:Lignin 12213:Chitin 12028:Alliin 11858:Others 11812:L-DOPA 11377:Others 10832:Butein 10579:Flavan 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Index

Capsaicinoids


/kæpˈssɪn/
/kæpˈsəsɪn/
Preferred IUPAC name
CAS Number
404-86-4
JSmol
Interactive image
Beilstein Reference
ChEBI
CHEBI:3374
ChEMBL
ChEMBL294199
ChemSpider
1265957
DrugBank
DB06774
ECHA InfoCard
100.006.337
Edit this at Wikidata
EC Number
IUPHAR/BPS
2486
KEGG
C06866
PubChem
1548943
UNII

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