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Epibatidine

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beetles, ants, mites, and flies. Daly and Charles noticed that epibatidine was produced from their diet due to their return trip to Ecuador in 1976 when they found that at one site, none of the frogs present produced alkaloids, such as epibatidine; they discovered that only the frogs at certain sites with the dietary means allowed these frogs to produce epibatidine. Overcoming the difficulties, the structure was eventually determined, and the first synthesis of epibatidine was completed in 1993. Many other synthesis methods have been developed since.
266: 45: 489: 543: 7728: 460:. These receptors are involved in the transmission of painful sensations, and in movement, among other functions. Epibatidine then causes numbness, and, eventually, paralysis. Doses are lethal when the paralysis causes respiratory arrest. Originally, it was thought that epibatidine could be useful as a drug. However, because of its unacceptable 802:, epibatidine needed only 2.5 μg/kg (11.98 nmol/kg) to initiate a pain-relieving effect whilst the same effect required approximately 10 mg/kg (35.05 μmol/kg) of morphine (approx. 2,900 times the efficacy.) Currently, only rudimentary research into epibatidine's effects has yet been performed; the drug has been administered only to 511:
Because of its analgesic effect, there was intense interest in epibatidine's use as a drug, because it was found not to be an opioid. This meant that it could potentially be used without fear of addiction. However, it was soon found that it cannot be used in humans because the dose resulting in toxic
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protected status in 1984. Furthermore, these frogs do not produce the toxin when bred and reared in captivity, because they do not synthesize epibatidine themselves. Like other poison dart frogs, they instead obtain it through their diet and then sequester it on their skin. Likely dietary sources are
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frogs collected by Daly and colleague, Charles Myers. Between 1974 and 1979, Daly and Myers collected the skins of nearly 3000 frogs from various sites in Ecuador, after finding that a small injection of a preparation from their skin caused analgesic (painkilling) effects in mice that resembled those
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of epibatidine are biologically active, and both have similar binding affinities to nAChRs Only the (+)-enantiomer does not induce tolerance. While this may be a potential therapeutic advantage over morphine, epibatidine has not entered clinical trials because even very small doses are lethal to
528:(in contrast, the naturally occurring compound is the (+)-enantiomer; the (−)-enantiomer does not occur naturally). It was later determined that the (+) and (-) enantiomers had equivalent analgesic as well as toxic effects. The process has proven to be quite productive, with a yield of about 40%. 448:
in 1974, but its structure was not fully elucidated until 1992. Whether epibatidine occurs naturally remains controversial due to challenges in conclusively identifying the compound from the limited samples collected by Daly. By the time that high-resolution spectrometry was used in 1991, there
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nerve discharge and increased arterial pressure. The nerve discharge effects can cause antinociception partially mediated by agonism of central nicotinic acetylcholine receptors at low doses of epibatidine; 5 μg/kg. At higher doses, however, epibatidine will cause paralysis and loss of
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Nicotinic acetylcholine receptors are found in the post-synaptic membranes of nerve cells. These receptors are an example of ion gated channels where binding by a ligand causes a conformational change allowing ions to cross the membrane into the cell. They propagate neurotransmission in the
485:. Despite its common name - Anthony's Poison Arrow frog - suggesting that it was used by natives when hunting, a paper written by Daly in 2000 claimed that there was no local folklore or folk medicine surrounding the frogs and that they were considered largely unimportant by the locals. 573:. ABT-594 retains analgesic properties while avoiding paralysis by still binding to receptors that control pain perception and having a low affinity for muscle-type nicotinic acetylcholine receptors (nAChR) reducing its paralysis effect. Other epibatidine analogs include 658:. When neurotransmitters bind to these receptors, ion channels open, allowing Na and Ca ions to move across the membrane. This depolarizes the post-synaptic membrane, inducing an action potential that propagates the signal. This signal will ultimately induce release of 1501:
Dallanoce C, Matera C, Pucci L, Gotti C, Clementi F, Amici MD, Micheli CD (January 2012). "Synthesis and binding affinity at α4β2 and α7 nicotinic acetylcholine receptors of new analogs of epibatidine and epiboxidine containing the 7-azabicyclohept-2-ene ring system".
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Dallanoce C, Magrone P, Matera C, Lo Presti L, De Amici M, Riganti L, et al. (December 2010). "Synthesis of novel chiral Δ2-isoxazoline derivatives related to ABT-418 and estimation of their affinity at neuronal nicotinic acetylcholine receptor subtypes".
779:,, it was initially thought to be very promising to replace morphine as a painkiller. However, the therapeutic concentration is very close to the toxic concentration. This means that even at a therapeutic dose (5 μg/kg), some epibatidine might bind to the 1465:
Dallanoce C, Matera C, De Amici M, Rizzi L, Pucci L, Gotti C, et al. (July 2012). "The enantiomers of epiboxidine and of two related analogs: synthesis and estimation of their binding affinity at α4β2 and α7 neuronal nicotinic acetylcholine receptors".
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Rizzi L, Dallanoce C, Matera C, Magrone P, Pucci L, Gotti C, et al. (August 2008). "Epiboxidine and novel-related analogues: a convenient synthetic approach and estimation of their affinity at neuronal nicotinic acetylcholine receptor subtypes".
670:) are also able to bind to the receptor and induce a similar, if not identical, response. Epibatidine has an extremely high affinity for nAChRs, depending on the receptor subtype, from 0.05 nM at the α4β2 subtype to 22 nM at the α7 subtype. 818:, a nicotinic acetylcholine receptor antagonist that is non-selective and non-competitive. Both the (+) and the (-) enantiomers of mecamylamine were seen to be efficient and both have the same affinity for nicotinic acetylcholine receptors. 523:
After the discovery of the structure of epibatidine, more than fifty ways to synthesize it in the laboratory have been devised. In the first reported example, a nine-step procedure produces the substance as a
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system, seizures, and, ultimately, death. The symptoms do, however, change drastically when lower doses are given. Mice became resistant to pain and heat with none of the negative effects of higher doses.
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remained less than one milligram of extract from Daly's samples, raising concerns about possible contamination. Samples from other batches of the same species of frog failed to yield epibatidine.
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In research on mice, administration of doses greater than 5 μg/kg of epibatidine caused a dose-dependent paralyzing effect on the organism. With doses over 5 μg/kg, symptoms included
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Bacher I, Wu B, Shytle DR, George TP (November 2009). "Mecamylamine - a nicotinic acetylcholine receptor antagonist with potential for the treatment of neuropsychiatric disorders".
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Also there is currently little information on the path of clearance from the body. Maximum concentration in the brain is reached at about 30 minutes after entering the body.
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Low doses of epibatidine will only affect the nAChRs, due to a higher affinity to nAChRs than to mAChRs. Higher doses, however, will cause epibatidine to bind to the mAChRs.
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and their derivatives. A synthesis of epibatidine, utilizing a microbial hydroxylation of an unactivated carbon in a 7-azanorbornane was published in 1999.
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of 22.8 μg/kg). Due to the small difference between its toxic concentration and antinociceptive concentration, its therapeutic uses are very limited.
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Sullivan JP, Bannon AW (1996). "Epibatidine: Pharmacological Properties of a Novel Nicotinic Acetylcholine Receptor Agonist and Analgesic Agent".
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Damaj MI, Creasy KR, Grove AD, Rosecrans JA, Martin BR (November 1994). "Pharmacological effects of epibatidine optical enantiomers".
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Watt AP, Hitzel L, Morrison D, Locker KL (October 2000). "Determination of the in vitro metabolism of (+)- and (-)-epibatidine".
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In addition to Corey's method, other notable methods include those of Broka, Huang and Shen, and Clayton and Regan.
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Epibatidine has a high analgesic potency, as stated above. Studies show it has a potency at least 200 times that of
728:) of epibatidine lies between 1.46 μg/kg and 13.98 μg/kg. This makes epibatidine somewhat more toxic than 7773: 6655: 6543: 6395: 6356: 3492: 619: 453: 1615:"Epibatidine, an alkaloid from the poison frog Epipedobates tricolor, is a powerful ganglionic depolarizing agent" 1125:
Donnelly-Roberts DL, Puttfarcken PS, Kuntzweiler TA, Briggs CA, Anderson DJ, Campbell JE, et al. (May 1998).
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Hogg RC, Raggenbass M, Bertrand D (2003). "Nicotinic acetylcholine receptors: from structure to brain function".
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Olivo HF, Hemenway MS (November 1999). "Total Synthesis of (+/-)-Epibatidine Using a Biocatalytic Approach".
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of epibatine that maintain analgesics effects, but without the toxicity, have been attempted. For example,
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Several total synthesis routes have been devised due to the relative scarcity of epibatidine in nature.
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InChI=1S/C11H13ClN2/c12-11-4-1-7(6-13-11)9-5-8-2-3-10(9)14-8/h1,4,6,8-10,14H,2-3,5H2/t8-,9+,10+/m0/s1
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studies seem to suggest that epibatidine is hardly, if at all, metabolized in the human body.
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Badio B, Daly JW (April 1994). "Epibatidine, a potent analgetic and nicotinic agonist".
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note: some toxins are produced by lower species and pass through intermediate species
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Huang DF, Shen TY (1993). "A versatile total synthesis of epibatidine and analogs".
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Daly JW, Garraffo HM, Spande TF, Decker MW, Sullivan JP, Williams M (April 2000).
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Daly JW, Garraffo HM, Spande TF, Decker MW, Sullivan JP, Williams M (April 2000).
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Epibatidine has several toxic consequences. Empirically proven effects include
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Epibatidine is toxic. Its toxicity stems from its ability to interact with
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Nickell JR, Grinevich VP, Siripurapu KB, Smith AM, Dwoskin LP (July 2013).
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Olivo HF, Hemenway MS (2002). "Recent syntheses of epibatidine. A review".
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The structure of epibatidine was elucidated in 1992, an effort hindered by
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property of epibatidine is believed to take place by its binding to the
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Clayton SC, Regan AC (1993). "A total synthesis of (±)-epibatidine".
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Fitch RW, Spande TF, Garraffo HM, Yeh HJ, Daly JW (March 2010).
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Epibatidine most effectively enters the body through injection.
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Epibatidine has two mechanisms of action: it can bind to either
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subtype of nicotinic receptors. Epibatidine also binds to the
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Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)
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The Journal of Pharmacology and Experimental Therapeutics
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The Journal of Pharmacology and Experimental Therapeutics
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property of epibatidine takes place after its binding to
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Fisher M, Huangfu D, Shen TY, Guyenet PG (August 1994).
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Broka CA (1994). "Synthetic approaches to epibatidine".
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starting from chloronicotinaldehyde is outlined below:
8208: 7804: 1725: 933: 929: 927: 925: 879: 775:. As the compound was not addictive nor did it cause 1973: 1728:
Reviews of Physiology, Biochemistry and Pharmacology
976: 1293:Broka CA (1993). "Total synthesis of epibatidine". 922: 1358:. Virginia Commonwealth University. Archived from 1009: 1007: 1005: 798:Compared to the gold standard in pain management, 569:has produced derivatives of epibatidine including 2979:1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 1158:Organic Preparations and Procedures International 1046: 934:Garraffo HM, Spande TF, Williams M (April 2009). 9440: 122: 80:)-(+)-6-(6-Chloro-3-pyridyl)-7-azabicycloheptane 4009:1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 1118: 1002: 97: 8703:Trimetaphan camsilate (trimethaphan camsylate) 1868: 982: 720:consciousness, coma and eventually death. The 8870: 8844:Acetylcholine metabolism/transport modulators 7758: 6389: 4941: 2089: 1773:"How Poison Frogs Avoid Poisoning Themselves" 1572: 1155: 991:. Berkeley, CA, USA: University of California 743:(increased blood pressure), paralysis in the 8839:Muscarinic acetylcholine receptor modulators 6472: 1889: 1608: 1606: 1604: 1504:Bioorganic & Medicinal Chemistry Letters 1422:Bioorganic & Medicinal Chemistry Letters 1243: 961: 4955: 1826:Acta Neurologica Scandinavica. Supplementum 8877: 8863: 7765: 7751: 6396: 6382: 4948: 4934: 2096: 2082: 1820:Sihver W, Långström B, Nordberg A (2002). 1684: 1195: 1193: 1191: 1189: 1187: 476:in 1974. It was isolated from the skin of 264: 162: 43: 34: 16:Toxic chemical from some poison dart frogs 7790:Tooltip Nicotinic acetylcholine receptors 7321:Androctonus australis hector insect toxin 2042: 1837: 1792: 1702: 1661: 1601: 1441: 1319: 1217: 1070: 905: 766: 546:The chemical synthesis of epibatidine by 182: 8333:Candocuronium iodide (chandonium iodide) 2023:Pharmacology, Biochemistry, and Behavior 1862: 1269: 1267: 967: 541: 487: 1788: 1786: 1643: 1540:European Journal of Medicinal Chemistry 1345: 1343: 1199: 1184: 512:symptoms is too low for it to be safe. 142: 9441: 8213:Tooltip negative allosteric modulators 7809:Tooltip positive allosteric modulators 1967: 1239: 1237: 1052: 613: 561:A number of approaches to discovering 255: 8858: 7746: 6377: 4929: 2077: 1924: 1770: 1292: 1273: 1264: 682:) are much higher than for nicotine. 608: 584: 242: 222: 9489:Chlorine-containing natural products 1783: 1340: 638:subtype and to a much lesser extent 593:with a structure similar to that of 556: 9484:Halogen-containing natural products 1691:The Journal of Biological Chemistry 1234: 983:Maxon J, Whittaker K (March 2009). 783:and cause adverse effects, such as 202: 113: 13: 6675:Staphylococcal Enterotoxin B (SEB) 1883:10.1111/j.1527-3458.1996.tb00288.x 781:muscarinic acetylcholine receptors 624:muscarinic acetylcholine receptors 458:muscarinic acetylcholine receptors 14: 9500: 8418:Dimethyltubocurarine (metocurine) 6040:Tetrahydrocannabinol (dronabinol) 2062: 1976:Expert Opinion on Pharmacotherapy 1685:Prince RJ, Sine SM (April 1998). 1356:Department of Medicinal Chemistry 642:(affinity 300-fold less than for 620:nicotinic acetylcholine receptors 7774:Nicotinic acetylcholine receptor 7727: 7726: 2974:1-(4-Methylphenyl)-2-aminobutane 1839:10.1034/j.1600-0404.2000.00304.x 1575:The Journal of Organic Chemistry 1349: 1065:(12). Oxford Journals: 945–950. 850:, neurotoxin closely related to 298: 295: 289: 8884: 8798:Meclofenoxate (centrophenoxine) 8123:Suxethonium (succinyldicholine) 8118:Suxamethonium (succinylcholine) 6759:Extracellular adenylate cyclase 3893:2-Phenyl-3,6-dimethylmorpholine 3587:N,alpha-Diethylphenylethylamine 2010: 1813: 1764: 1719: 1678: 1637: 1566: 1530: 1494: 1458: 1412: 1387: 1366: 1313: 1286: 814:The antidote to epibatidine is 751: 691:muscle-type nicotinic receptors 389:Key:NLPRAJRHRHZCQQ-IVZWLZJFSA-N 9160:Tetramethylenedisulfotetramine 5808:Aspirin (acetylsalicylic acid) 4488:Troparil (β-CPT, WIN 35,065-2) 3089:2-Amino-1,2-dihydronaphthalene 2103: 1771:Olena A (September 21, 2017). 1650:British Journal of Anaesthesia 1206:British Journal of Anaesthesia 1149: 1079: 873: 472:Epibatidine was discovered by 283: 1: 8834:Receptor/signaling modulators 8488:Hexamethonium (benzohexonium) 6911:Fibronectin binding protein A 1910:10.1016/s0021-9673(00)00597-5 1307:10.1016/s0040-4039(00)73674-4 1258:10.1016/S0040-4039(00)60162-4 867: 444:genus. It was discovered by 9469:Halogen-containing alkaloids 1945:10.1016/0006-8993(94)91950-x 1552:10.1016/j.ejmech.2010.09.009 1334:10.1016/0040-4039(93)88063-o 1276:Medicinal Chemistry Research 626:(mAChR). Specifically, the 589:Epibatidine is a piperidine 515: 7: 8568:Methorphan (racemethorphan) 7898:Bephenium hydroxynaphthoate 6652:Staphylococcus aureus alpha 6630:Panton–Valentine leukocidin 5450:Paracetamol (acetaminophen) 4597:3,3-Diphenylcyclobutanamine 4137:2-Diphenylmethylpyrrolidine 4024:3,4-Dichloromethylphenidate 4019:2-Methyl-3-phenylpiperidine 1898:Journal of Chromatography A 1072:10.1525/bisi.1999.49.12.945 1053:Lasley EN (December 1999). 886:Journal of Natural Products 821: 809: 806:for analysis at this time. 707: 364:ClC1=CC=C(2C3()CC2()N3)C=N1 10: 9505: 7948:Dimethylphenylpiperazinium 6670:Toxic shock syndrome toxin 3592:N,N-Dimethylphenethylamine 2069:Epibatidine at chemsoc.org 1516:10.1016/j.bmcl.2011.12.052 1434:10.1016/j.bmcl.2008.07.016 601:oily substance which is a 467: 273:Chemical and physical data 18: 9400: 9364: 9336: 9223: 9145: 9117: 9039: 9006: 8983: 8892: 8826: 8740: 8201: 7797: 7783: 7722: 7709: 7647: 7567:(+)-Allopumiliotoxin 267A 7554: 7528: 7517: 7472: 7414: 7308: 7297: 7066: 6923: 6894: 6830: 6767: 6714: 6687: 6640: 6615: 6606: 6579: 6492: 6483: 6463: 6452: 6334: 6253: 6210: 6188: 6151:Tricyclic antidepressants 6107: 6059: 6048: 6010: 5965: 5914: 5798: 5765: 5714: 5650: 5614: 5524: 5515: 5424: 5222: 5040: 4981: 4972: 4910: 4584: 4511: 4313: 4305:Phenylpiracetam hydrazide 4285: 4127: 3999: 3911: 3828: 2964: 2911: 2868: 2810: 2637: 2469: 2436: 2368: 2285: 2222: 2164:8-Cyclopentyltheophylline 2149: 2111: 2035:10.1016/j.pbb.2013.04.005 1988:10.1517/14656560903329102 1740:10.1007/s10254-003-0005-1 1170:10.1080/00304940209355744 656:peripheral nervous system 397: 372: 352: 342: 320: 307: 277: 272: 253: 233: 213: 193: 173: 153: 133: 108: 88: 56: 51: 42: 33: 8808:Phosphatidylethanolamine 6960:beta-Nitropropionic acid 5485:+propyphenazone/caffeine 2629:Phthalimidopropiophenone 1644:Traynor JR (July 1998). 1200:Traynor JR (July 1998). 424:that is secreted by the 19:Not to be confused with 9365:Cholinergic neurotoxins 8588:Morphanol (racemorphan) 8528:Laudexium (laudolissin) 7938:Desformylflustrabromine 6744:Heat-labile enterotoxin 6735:heat-stable enterotoxin 4039:4-Methylmethylphenidate 4034:4-Fluoromethylphenidate 3143:β-Phenylmethamphetamine 3099:5-(2-Aminopropyl)indole 3034:4-Fluoromethamphetamine 2989:2-Fluoromethamphetamine 2594:Methylenedioxycathinone 1704:10.1074/jbc.273.14.7843 1401:. University of Bristol 1092:Natural Product Reports 1020:Natural Product Reports 6853:Bacillus thuringiensis 5335:Pethidine (meperidine) 4363:Dichloropane (RTI-111) 3168:3-Benzhydrylmorpholine 3138:β-Methylphenethylamine 3014:3-Fluoroethamphetamine 2999:2-Phenyl-3-aminobutane 1795:Molecular Pharmacology 1646:"Epibatidine and pain" 1202:"Epibatidine and pain" 767:Potential medical uses 550: 535:synthesis reported by 496: 9392:Hemicholinium mustard 9372:Acetylcholine mustard 9195:Chlorophenylsilatrane 8793:Glycerophosphocholine 5956:+paracetamol/caffeine 5934:Metamizole (dipyrone) 5868:Morpholine salicylate 5812:+paracetamol/caffeine 4478:Salicylmethylecgonine 4114:Serdexmethylphenidate 3838:3-Fluorophenmetrazine 3537:Dextromethamphetamine 3483:MDMA (midomafetamine) 3069:a-Ethylphenethylamine 2479:3-Fluoromethcathinone 2151:Adenosine antagonists 987:Epipedobates anthonyi 955:10.3987/REV-08-SR(D)5 840:(and closely related 545: 493:Epipedobates tricolor 491: 478:Epipedobates anthonyi 431:Epipedobates anthonyi 9387:Ethylcholine mustard 8788:Dimethylethanolamine 8653:Rapacuronium bromide 8633:Pipecuronium bromide 8473:Gantacurium chloride 8433:Dizocilpine (MK-801) 8018:MEM-63,908 (RG-3487) 7968:Ethoxysebacylcholine 6754:Pseudomonas exotoxin 6079:Gabapentin enacarbil 5873:Potassium salicylate 5863:Magnesium salicylate 5858:Imidazole salicylate 5685:Indometacin farnesil 5081:Diamorphine (heroin) 5048:Acetyldihydrocodeine 4812:Naphthylaminopropane 4323:4-fluorotropacocaine 3409:5-Iodo-2-aminoindane 3404:4-Hydroxyamphetamine 3241:Dimethoxyamphetamine 3019:3-Methoxyamphetamine 2370:Arylcyclohexylamines 2169:8-Phenyltheophylline 2159:8-Chlorotheophylline 1362:on December 5, 2010. 9338:Bicyclic phosphates 8960:Spooky toxin (SsTx) 8803:Phosphatidylcholine 8688:Threohydrobupropion 8673:Stercuronium iodide 8608:Pancuronium bromide 5828:Carbasalate calcium 3898:Pseudophenmetrazine 3710:Phenylpropanolamine 3630:-Norpseudoephedrine 3597:Naphthylamphetamine 3541:Levomethamphetamine 3468:MDA (tenamfetamine) 3310:Ethylnorepinephrine 3246:Dimethylamphetamine 3029:4-Fluoroamphetamine 3024:3-Methylamphetamine 3009:3-Fluoroamphetamine 2984:2-Fluoroamphetamine 2257:Levopropylhexedrine 1663:10.1093/bja/81.1.69 1399:School of Chemistry 1246:Tetrahedron Letters 1219:10.1093/bja/81.1.69 970:The Right Chemistry 968:Schwarcz J (2012). 732:(with an average LD 614:Mechanism of action 567:Abbott Laboratories 348:1.2 ± 0.1 g/cm 30: 9464:Pyridine alkaloids 9454:Nicotinic agonists 8723:Vecuronium bromide 8663:Rocuronium bromide 8573:Methyllycaconitine 8498:Hydroxynorketamine 8393:Dextropropoxyphene 8378:Dehydronorketamine 8368:Dacuronium bromide 7670:Alpha-Bungarotoxin 6840:Lipopolysaccharide 6798:Pore-forming toxin 6361:Never to phase III 6266:Analgesic adjuvant 6167:1.7/1.8-selective: 5833:Choline salicylate 5260:Dextropropoxyphene 4088:Dexmethylphenidate 4074:Isopropylphenidate 4029:4-Benzylpiperidine 4014:2-Benzylpiperidine 3419:Indanylamphetamine 2514:4-Methylpentedrone 2499:4-Methylbuphedrone 1480:10.1002/chir.22052 722:median lethal dose 699:Both (+)- and (-)- 609:Biological effects 585:Chemical structure 563:structural analogs 551: 497: 26: 9436: 9435: 9200:Sulfuryl fluoride 8852: 8851: 8813:Phosphorylcholine 8751: 8736: 8735: 8533:Levacetylmethadol 8413:Dihydrochandonium 8293:sodium thiopental 7963:Ethanol (alcohol) 7740: 7739: 7705: 7704: 7675:Beta-Bungarotoxin 7619:Pumiliotoxin 251D 7513: 7512: 6919: 6918: 6906:Clumping factor A 6826: 6825: 6710: 6709: 6683: 6682: 6602: 6601: 6371: 6370: 6206: 6205: 6190:Potassium openers 6127:Local anesthetics 6069:Alcohol (ethanol) 6006: 6005: 5905:methyl salicylate 5893:Sodium salicylate 5780:Meclofenamic acid 5455:+aspirin/caffeine 5420: 5419: 4923: 4922: 4862:Rubidium chloride 4333:Altropane (IACFT) 4247:Indapyrophenidone 4069:Methylnaphthidate 3830:Phenylmorpholines 3750:Propylamphetamine 3629: 3441: 3230: 3118:Dextroamphetamine 2609:N-Ethylbuphedrone 2549:Dimethylcathinone 2504:4-Methylcathinone 2262:Methylhexaneamine 1982:(16): 2709–2721. 1749:978-3-540-01365-5 1697:(14): 7843–7849. 1587:10.1021/jo991141q 1581:(24): 8968–8969. 1546:(12): 5594–5601. 1428:(16): 4651–4654. 1328:(28): 4477–4480. 1301:(20): 3251–3254. 1252:(46): 7493–7496. 898:10.1021/np900727e 842:homobatrachotoxin 557:Synthetic analogs 462:therapeutic index 436:poison dart frogs 420:is a chlorinated 415: 414: 333:Interactive image 9496: 9459:Amphibian toxins 8879: 8872: 8865: 8856: 8855: 8745: 8683:Thiocolchicoside 8493:Hydroxybupropion 8388:Dextromethorphan 8260:Allopregnanolone 8214: 8210: 8113:Suberyldicholine 7823:6-Chloronicotine 7810: 7806: 7795: 7794: 7791: 7787: 7767: 7760: 7753: 7744: 7743: 7730: 7729: 7658: 7614:Histrionicotoxin 7560: 7534: 7526: 7525: 7478: 7432:Alpha-latrotoxin 7420: 7314: 7306: 7305: 7038:Sterigmatocystin 6990:, Fumonisin B3, 6954:epsilon-amanitin 6873:B. thuringiensis 6702:Diphtheria toxin 6645: 6613: 6612: 6582: 6498: 6490: 6489: 6481: 6480: 6470: 6469: 6461: 6460: 6398: 6391: 6384: 6375: 6374: 6061:Calcium blockers 6057: 6056: 5953: 5902: 5728: 5716:COX-2 inhibitors 5682: 5601:Tiaprofenic acid 5572: 5559: 5551: 5522: 5521: 5399: 5179: 5118: 5090: 5062: 4979: 4978: 4950: 4943: 4936: 4927: 4926: 4343:CFT (WIN 35,428) 4328:4'-Fluorococaine 4192:Diphenylprolinol 4059:Ethylnaphthidate 4054:Diphenylpyraline 3690:Phenpromethamine 3627: 3562:Methoxyphenamine 3552:Methoxyphenamine 3453:Lisdexamfetamine 3439: 3353:Levofenfluramine 3228: 3188:Chlorphentermine 2921:4-Methylaminorex 2614:N-Ethylhexedrone 2098: 2091: 2084: 2075: 2074: 2057: 2056: 2046: 2014: 2008: 2007: 1971: 1965: 1964: 1928: 1922: 1921: 1893: 1887: 1886: 1871:CNS Drug Reviews 1866: 1860: 1859: 1841: 1817: 1811: 1810: 1790: 1781: 1780: 1768: 1762: 1761: 1723: 1717: 1716: 1706: 1682: 1676: 1675: 1665: 1641: 1635: 1634: 1610: 1599: 1598: 1570: 1564: 1563: 1534: 1528: 1527: 1498: 1492: 1491: 1462: 1456: 1455: 1445: 1416: 1410: 1409: 1407: 1406: 1391: 1385: 1384: 1382: 1381: 1370: 1364: 1363: 1347: 1338: 1337: 1322:Tetrahedron Lett 1317: 1311: 1310: 1295:Tetrahedron Lett 1290: 1284: 1283: 1271: 1262: 1261: 1241: 1232: 1231: 1221: 1197: 1182: 1181: 1153: 1147: 1146: 1122: 1116: 1115: 1104:10.1039/A900728H 1083: 1077: 1076: 1074: 1050: 1044: 1043: 1032:10.1039/a900728h 1011: 1000: 999: 997: 996: 980: 974: 973: 965: 959: 958: 940: 931: 920: 919: 909: 877: 828:6-Chloronicotine 533:enantioselective 411: 410: 403: 335: 315: 300: 297: 291: 285: 268: 257: 246: 226: 206: 186: 166: 146: 126: 116: 115: 101: 47: 38: 31: 29: 25: 9504: 9503: 9499: 9498: 9497: 9495: 9494: 9493: 9474:Chloropyridines 9439: 9438: 9437: 9432: 9413:Dimethylmercury 9408:Dimethylcadmium 9396: 9382:Choline mustard 9360: 9332: 9219: 9190:Phenylsilatrane 9141: 9113: 9035: 9002: 8993:Botulinum toxin 8979: 8888: 8883: 8853: 8848: 8822: 8744: 8732: 8338:Chlorisondamine 8212: 8205: 8197: 7808: 7801: 7789: 7779: 7771: 7741: 7736: 7718: 7701: 7697:Cardiotoxin III 7653: 7648: 7643: 7555: 7550: 7529: 7521: 7509: 7473: 7468: 7415: 7410: 7309: 7301: 7293: 7197:Resiniferatoxin 7062: 6915: 6897: 6890: 6855:delta endotoxin 6822: 6763: 6749:Pertussis toxin 6717: 6706: 6679: 6641: 6636: 6598: 6594:Listeriolysin O 6580: 6575: 6493: 6475: 6455: 6448: 6402: 6372: 6367: 6366: 6351:Clinical trials 6330: 6311:Phenazopyridine 6249: 6230:Cyclobenzaprine 6202: 6184: 6166: 6109:Sodium blockers 6103: 6051: 6044: 6002: 5961: 5951: 5910: 5900: 5794: 5790:Tolfenamic acid 5775:Flufenamic acid 5761: 5726: 5710: 5680: 5646: 5610: 5570: 5557: 5549: 5511: 5475:+metoclopramide 5416: 5397: 5218: 5177: 5116: 5099:Dihydromorphine 5088: 5060: 5036: 4968: 4954: 4924: 4919: 4906: 4807:Methiopropamine 4580: 4507: 4433:RTI-121 (IPCIT) 4309: 4300:Phenylpiracetam 4281: 4123: 4109:Propylphenidate 4084:Methylphenidate 4044:Desoxypipradrol 3995: 3907: 3883:Phendimetrazine 3824: 3800:Tranylcypromine 3755:Pseudoephedrine 3622:Normetanephrine 3617:Norfenfluramine 3533:Methamphetamine 3349:Dexfenfluramine 3122:Levoamphetamine 3104:2-Aminotetralin 2966:Phenethylamines 2960: 2907: 2864: 2806: 2633: 2574:Isoethcathinone 2465: 2432: 2364: 2281: 2272:Propylhexedrine 2218: 2145: 2107: 2102: 2065: 2060: 2015: 2011: 1972: 1968: 1929: 1925: 1904:(1–2): 229–38. 1894: 1890: 1867: 1863: 1818: 1814: 1791: 1784: 1769: 1765: 1750: 1724: 1720: 1683: 1679: 1642: 1638: 1611: 1602: 1571: 1567: 1535: 1531: 1499: 1495: 1463: 1459: 1417: 1413: 1404: 1402: 1393: 1392: 1388: 1379: 1377: 1372: 1371: 1367: 1348: 1341: 1318: 1314: 1291: 1287: 1272: 1265: 1242: 1235: 1198: 1185: 1154: 1150: 1123: 1119: 1084: 1080: 1051: 1047: 1012: 1003: 994: 992: 981: 977: 972:. Random House. 966: 962: 938: 932: 923: 878: 874: 870: 824: 812: 769: 754: 735: 727: 710: 678:(and thus also 616: 611: 587: 559: 518: 470: 406: 404: 401:(what is this?) 398: 393: 390: 385: 380: 379: 368: 365: 360: 359: 338: 313: 303: 294: 288: 249: 229: 209: 189: 169: 149: 129: 112: 104: 84: 81: 64: 63: 24: 17: 12: 11: 5: 9502: 9492: 9491: 9486: 9481: 9476: 9471: 9466: 9461: 9456: 9451: 9434: 9433: 9431: 9430: 9428:Tetraethyllead 9425: 9420: 9418:Toxopyrimidine 9415: 9410: 9404: 9402: 9398: 9397: 9395: 9394: 9389: 9384: 9379: 9374: 9368: 9366: 9362: 9361: 9359: 9358: 9353: 9348: 9342: 9340: 9334: 9333: 9331: 9330: 9325: 9320: 9315: 9310: 9305: 9300: 9295: 9290: 9285: 9280: 9275: 9270: 9265: 9260: 9255: 9250: 9245: 9243:Novichok agent 9240: 9235: 9229: 9227: 9221: 9220: 9218: 9217: 9212: 9207: 9202: 9197: 9192: 9187: 9182: 9177: 9172: 9167: 9162: 9157: 9151: 9149: 9143: 9142: 9140: 9139: 9134: 9129: 9123: 9121: 9115: 9114: 9112: 9111: 9106: 9101: 9096: 9091: 9086: 9081: 9076: 9071: 9066: 9061: 9056: 9051: 9045: 9043: 9037: 9036: 9034: 9033: 9028: 9023: 9018: 9012: 9010: 9004: 9003: 9001: 9000: 8995: 8989: 8987: 8981: 8980: 8978: 8977: 8972: 8970:Zetekitoxin AB 8967: 8962: 8957: 8952: 8947: 8942: 8937: 8932: 8927: 8922: 8917: 8912: 8907: 8902: 8896: 8894: 8890: 8889: 8882: 8881: 8874: 8867: 8859: 8850: 8849: 8847: 8846: 8841: 8836: 8831: 8827: 8824: 8823: 8821: 8820: 8815: 8810: 8805: 8800: 8795: 8790: 8785: 8780: 8775: 8765: 8760: 8754: 8752: 8738: 8737: 8734: 8733: 8731: 8730: 8725: 8720: 8715: 8710: 8705: 8700: 8695: 8690: 8685: 8680: 8675: 8670: 8665: 8660: 8655: 8650: 8645: 8640: 8635: 8630: 8625: 8620: 8615: 8610: 8605: 8600: 8595: 8590: 8585: 8580: 8575: 8570: 8565: 8560: 8555: 8550: 8545: 8540: 8535: 8530: 8525: 8520: 8518:Kynurenic acid 8515: 8510: 8505: 8500: 8495: 8490: 8485: 8480: 8475: 8470: 8465: 8460: 8455: 8450: 8445: 8440: 8435: 8430: 8425: 8420: 8415: 8410: 8405: 8400: 8395: 8390: 8385: 8380: 8375: 8370: 8365: 8360: 8355: 8350: 8345: 8340: 8335: 8330: 8325: 8320: 8315: 8312:κ-bungarotoxin 8308:α-bungarotoxin 8301: 8296: 8282: 8277: 8272: 8267: 8262: 8257: 8252: 8247: 8246:, many others) 8236:α-bungarotoxin 8229: 8224: 8218: 8216: 8199: 8198: 8196: 8195: 8190: 8185: 8180: 8175: 8170: 8168:Tribendimidine 8165: 8160: 8155: 8150: 8145: 8140: 8135: 8130: 8125: 8120: 8115: 8110: 8105: 8100: 8095: 8093:Sebacylcholine 8090: 8085: 8080: 8075: 8070: 8065: 8060: 8055: 8050: 8045: 8040: 8035: 8025: 8020: 8015: 8010: 8005: 8000: 7995: 7990: 7985: 7980: 7975: 7970: 7965: 7960: 7955: 7950: 7945: 7940: 7935: 7930: 7925: 7920: 7915: 7910: 7908:Butyrylcholine 7905: 7900: 7895: 7890: 7885: 7880: 7875: 7870: 7865: 7860: 7855: 7850: 7845: 7840: 7835: 7830: 7825: 7820: 7814: 7812: 7792: 7781: 7780: 7770: 7769: 7762: 7755: 7747: 7738: 7737: 7735: 7734: 7723: 7720: 7719: 7717: 7716: 7710: 7707: 7706: 7703: 7702: 7700: 7699: 7694: 7689: 7684: 7679: 7678: 7677: 7672: 7661: 7659: 7645: 7644: 7642: 7641: 7639:Zetekitoxin AB 7636: 7631: 7626: 7621: 7616: 7611: 7606: 7605: 7604: 7599: 7594: 7589: 7584: 7574: 7569: 7563: 7561: 7552: 7551: 7549: 7548: 7543: 7537: 7535: 7523: 7515: 7514: 7511: 7510: 7508: 7507: 7502: 7497: 7492: 7487: 7481: 7479: 7470: 7469: 7467: 7466: 7461: 7456: 7451: 7446: 7441: 7436: 7435: 7434: 7423: 7421: 7412: 7411: 7409: 7408: 7403: 7398: 7393: 7388: 7383: 7378: 7373: 7368: 7363: 7358: 7353: 7348: 7343: 7338: 7333: 7328: 7323: 7317: 7315: 7303: 7295: 7294: 7292: 7291: 7286: 7285: 7284: 7279: 7269: 7264: 7259: 7254: 7249: 7244: 7239: 7234: 7229: 7224: 7219: 7214: 7209: 7204: 7199: 7194: 7189: 7187:Pseudaconitine 7184: 7179: 7174: 7169: 7164: 7159: 7154: 7149: 7144: 7139: 7134: 7129: 7127:Djenkolic acid 7124: 7119: 7114: 7109: 7104: 7099: 7094: 7089: 7084: 7079: 7073: 7071: 7064: 7063: 7061: 7060: 7055: 7050: 7045: 7040: 7035: 7030: 7025: 7020: 7015: 7010: 7005: 7000: 6995: 6977: 6972: 6967: 6962: 6957: 6950:gamma-amanitin 6942:alpha-amanitin 6935: 6929: 6927: 6921: 6920: 6917: 6916: 6914: 6913: 6908: 6902: 6900: 6892: 6891: 6889: 6888: 6887: 6886: 6881: 6869: 6868: 6867: 6862: 6849: 6848: 6847: 6836: 6834: 6828: 6827: 6824: 6823: 6821: 6820: 6819: 6818: 6802: 6801: 6800: 6788: 6787: 6786: 6773: 6771: 6765: 6764: 6762: 6761: 6756: 6751: 6746: 6737: 6729: 6722: 6720: 6712: 6711: 6708: 6707: 6705: 6704: 6699: 6693: 6691: 6689:Actinomycetota 6685: 6684: 6681: 6680: 6678: 6677: 6672: 6667: 6662: 6648: 6646: 6643:Staphylococcus 6638: 6637: 6635: 6634: 6633: 6632: 6622: 6616: 6610: 6604: 6603: 6600: 6599: 6597: 6596: 6591: 6585: 6583: 6577: 6576: 6574: 6573: 6572: 6571: 6559: 6558: 6557: 6552: 6540: 6539: 6538: 6533: 6521: 6520: 6519: 6514: 6501: 6499: 6487: 6478: 6467: 6458: 6450: 6449: 6447: 6446: 6445: 6444: 6439: 6434: 6429: 6424: 6419: 6414: 6401: 6400: 6393: 6386: 6378: 6369: 6368: 6365: 6364: 6363: 6362: 6359: 6348: 6342: 6336: 6335: 6332: 6331: 6329: 6328: 6323: 6318: 6313: 6308: 6306:Methoxyflurane 6303: 6298: 6293: 6288: 6283: 6278: 6273: 6268: 6263: 6257: 6255: 6251: 6250: 6248: 6247: 6242: 6237: 6232: 6227: 6222: 6216: 6214: 6208: 6207: 6204: 6203: 6201: 6200: 6194: 6192: 6186: 6185: 6183: 6182: 6177: 6172: 6164: 6159: 6158: 6148: 6143: 6138: 6124: 6119: 6113: 6111: 6105: 6104: 6102: 6101: 6096: 6091: 6086: 6081: 6076: 6071: 6065: 6063: 6054: 6046: 6045: 6043: 6042: 6037: 6032: 6027: 6022: 6016: 6014: 6008: 6007: 6004: 6003: 6001: 6000: 5995: 5990: 5985: 5980: 5975: 5969: 5967: 5963: 5962: 5960: 5959: 5949:Propyphenazone 5946: 5941: 5936: 5931: 5926: 5924:Aminophenazone 5920: 5918: 5912: 5911: 5909: 5908: 5895: 5890: 5885: 5880: 5875: 5870: 5865: 5860: 5855: 5850: 5845: 5840: 5835: 5830: 5825: 5820: 5815: 5804: 5802: 5796: 5795: 5793: 5792: 5787: 5785:Mefenamic acid 5782: 5777: 5771: 5769: 5763: 5762: 5760: 5759: 5754: 5749: 5744: 5739: 5734: 5720: 5718: 5712: 5711: 5709: 5708: 5703: 5698: 5693: 5688: 5675: 5670: 5665: 5660: 5654: 5652: 5648: 5647: 5645: 5644: 5639: 5634: 5629: 5624: 5618: 5616: 5612: 5611: 5609: 5608: 5603: 5598: 5593: 5588: 5583: 5578: 5565: 5544: 5539: 5534: 5528: 5526: 5519: 5513: 5512: 5510: 5509: 5504: 5499: 5494: 5493: 5492: 5487: 5482: 5477: 5472: 5467: 5462: 5457: 5447: 5442: 5437: 5431: 5429: 5422: 5421: 5418: 5417: 5415: 5414: 5409: 5392: 5387: 5382: 5377: 5372: 5367: 5362: 5357: 5352: 5347: 5342: 5337: 5332: 5327: 5322: 5317: 5312: 5307: 5302: 5297: 5292: 5282: 5277: 5272: 5267: 5262: 5257: 5255:Dextromoramide 5252: 5247: 5242: 5237: 5232: 5226: 5224: 5220: 5219: 5217: 5216: 5211: 5206: 5201: 5172: 5167: 5162: 5157: 5152: 5147: 5142: 5137: 5135:Hydromorphinol 5132: 5111: 5106: 5101: 5096: 5086:Dihydrocodeine 5083: 5078: 5073: 5068: 5055: 5053:Benzylmorphine 5050: 5044: 5042: 5038: 5037: 5035: 5034: 5029: 5024: 5019: 5009: 5008: 5007: 5002: 4991: 4989: 4976: 4970: 4969: 4953: 4952: 4945: 4938: 4930: 4921: 4920: 4911: 4908: 4907: 4905: 4904: 4899: 4894: 4889: 4884: 4879: 4874: 4869: 4864: 4859: 4854: 4849: 4844: 4839: 4834: 4829: 4824: 4819: 4814: 4809: 4804: 4802:Methastyridone 4799: 4797:Methamnetamine 4794: 4789: 4784: 4779: 4774: 4769: 4764: 4759: 4754: 4749: 4744: 4739: 4734: 4729: 4724: 4719: 4714: 4709: 4704: 4699: 4694: 4689: 4684: 4679: 4674: 4669: 4664: 4659: 4654: 4649: 4644: 4639: 4634: 4629: 4624: 4619: 4614: 4609: 4604: 4602:Amfonelic acid 4599: 4594: 4588: 4586: 4582: 4581: 4579: 4578: 4573: 4568: 4563: 4558: 4553: 4548: 4543: 4538: 4533: 4528: 4523: 4517: 4515: 4509: 4508: 4506: 4505: 4500: 4495: 4490: 4485: 4480: 4475: 4470: 4465: 4460: 4455: 4450: 4445: 4440: 4435: 4430: 4425: 4420: 4415: 4410: 4405: 4400: 4395: 4390: 4385: 4380: 4375: 4370: 4365: 4360: 4355: 4350: 4348:β-CIT (RTI-55) 4345: 4340: 4335: 4330: 4325: 4319: 4317: 4311: 4310: 4308: 4307: 4302: 4297: 4291: 4289: 4283: 4282: 4280: 4279: 4274: 4269: 4264: 4259: 4254: 4249: 4244: 4239: 4234: 4229: 4224: 4219: 4214: 4209: 4204: 4199: 4194: 4189: 4184: 4179: 4174: 4169: 4164: 4159: 4154: 4149: 4144: 4139: 4133: 4131: 4125: 4124: 4122: 4121: 4116: 4111: 4106: 4101: 4096: 4091: 4081: 4076: 4071: 4066: 4064:Ethylphenidate 4061: 4056: 4051: 4046: 4041: 4036: 4031: 4026: 4021: 4016: 4011: 4005: 4003: 3997: 3996: 3994: 3993: 3988: 3983: 3978: 3973: 3968: 3963: 3958: 3953: 3948: 3943: 3938: 3933: 3928: 3923: 3917: 3915: 3909: 3908: 3906: 3905: 3900: 3895: 3890: 3885: 3880: 3875: 3870: 3865: 3860: 3855: 3850: 3845: 3840: 3834: 3832: 3826: 3825: 3823: 3822: 3817: 3812: 3807: 3802: 3797: 3792: 3787: 3782: 3777: 3772: 3769:Levosalbutamol 3762: 3757: 3752: 3747: 3742: 3737: 3732: 3727: 3722: 3717: 3712: 3707: 3702: 3697: 3692: 3687: 3682: 3677: 3672: 3667: 3662: 3657: 3652: 3647: 3642: 3637: 3632: 3624: 3619: 3614: 3609: 3607:Norepinephrine 3604: 3599: 3594: 3589: 3584: 3579: 3574: 3569: 3564: 3559: 3554: 3549: 3544: 3530: 3525: 3520: 3515: 3510: 3505: 3500: 3495: 3490: 3485: 3480: 3475: 3470: 3465: 3460: 3455: 3450: 3445: 3436: 3431: 3426: 3421: 3416: 3411: 3406: 3401: 3396: 3391: 3386: 3381: 3376: 3371: 3366: 3361: 3356: 3342: 3337: 3332: 3327: 3322: 3317: 3315:Etilamfetamine 3312: 3307: 3302: 3297: 3292: 3287: 3282: 3277: 3272: 3267: 3253: 3248: 3243: 3238: 3233: 3225: 3220: 3215: 3210: 3205: 3200: 3195: 3190: 3185: 3180: 3175: 3170: 3165: 3160: 3155: 3150: 3145: 3140: 3135: 3130: 3125: 3111: 3106: 3101: 3096: 3091: 3086: 3081: 3076: 3071: 3066: 3061: 3056: 3051: 3046: 3041: 3036: 3031: 3026: 3021: 3016: 3011: 3006: 3001: 2996: 2991: 2986: 2981: 2976: 2970: 2968: 2962: 2961: 2959: 2958: 2953: 2948: 2943: 2938: 2933: 2928: 2923: 2917: 2915: 2909: 2908: 2906: 2905: 2900: 2895: 2890: 2885: 2880: 2874: 2872: 2866: 2865: 2863: 2862: 2857: 2852: 2847: 2842: 2837: 2832: 2827: 2822: 2816: 2814: 2808: 2807: 2805: 2804: 2799: 2794: 2789: 2784: 2779: 2774: 2769: 2764: 2759: 2754: 2749: 2744: 2739: 2734: 2729: 2724: 2719: 2714: 2709: 2704: 2699: 2694: 2689: 2684: 2679: 2674: 2669: 2664: 2659: 2654: 2649: 2643: 2641: 2635: 2634: 2632: 2631: 2626: 2621: 2616: 2611: 2606: 2601: 2596: 2591: 2586: 2581: 2576: 2571: 2566: 2561: 2556: 2551: 2546: 2541: 2536: 2531: 2526: 2521: 2516: 2511: 2506: 2501: 2496: 2491: 2486: 2481: 2475: 2473: 2467: 2466: 2464: 2463: 2458: 2453: 2448: 2442: 2440: 2434: 2433: 2431: 2430: 2425: 2420: 2415: 2410: 2405: 2400: 2395: 2390: 2385: 2383:Dieticyclidine 2380: 2374: 2372: 2366: 2365: 2363: 2362: 2357: 2352: 2347: 2342: 2337: 2332: 2327: 2322: 2317: 2312: 2307: 2302: 2297: 2291: 2289: 2283: 2282: 2280: 2279: 2277:Tuaminoheptane 2274: 2269: 2264: 2259: 2254: 2249: 2244: 2239: 2234: 2232:Cyclopentamine 2228: 2226: 2220: 2219: 2217: 2216: 2211: 2206: 2201: 2196: 2194:Istradefylline 2191: 2186: 2181: 2176: 2171: 2166: 2161: 2155: 2153: 2147: 2146: 2144: 2143: 2138: 2133: 2128: 2123: 2117: 2115: 2109: 2108: 2101: 2100: 2093: 2086: 2078: 2072: 2071: 2064: 2063:External links 2061: 2059: 2058: 2009: 1966: 1939:(1–2): 34–40. 1933:Brain Research 1923: 1888: 1861: 1812: 1782: 1763: 1748: 1718: 1677: 1636: 1625:(2): 702–707. 1600: 1565: 1529: 1510:(2): 829–832. 1493: 1474:(7): 543–551. 1457: 1411: 1386: 1376:. Mongabay.com 1365: 1339: 1312: 1285: 1263: 1233: 1183: 1148: 1137:(2): 777–786. 1117: 1098:(2): 131–135. 1078: 1045: 1026:(2): 131–135. 1001: 975: 960: 949:(1): 207–217. 921: 892:(3): 331–337. 871: 869: 866: 865: 864: 859: 854: 845: 835: 830: 823: 820: 811: 808: 768: 765: 753: 750: 733: 725: 709: 706: 664:norepinephrine 615: 612: 610: 607: 586: 583: 558: 555: 517: 514: 469: 466: 413: 412: 395: 394: 392: 391: 388: 386: 383: 375: 374: 373: 370: 369: 367: 366: 363: 355: 354: 353: 350: 349: 346: 340: 339: 337: 336: 328: 326: 318: 317: 311: 305: 304: 301: 292: 286: 281: 275: 274: 270: 269: 259: 251: 250: 248: 247: 239: 237: 231: 230: 228: 227: 219: 217: 211: 210: 208: 207: 199: 197: 191: 190: 188: 187: 179: 177: 171: 170: 168: 167: 159: 157: 151: 150: 148: 147: 139: 137: 131: 130: 128: 127: 119: 117: 106: 105: 103: 102: 94: 92: 86: 85: 83: 82: 67: 59: 58: 57: 54: 53: 49: 48: 40: 39: 15: 9: 6: 4: 3: 2: 9501: 9490: 9487: 9485: 9482: 9480: 9477: 9475: 9472: 9470: 9467: 9465: 9462: 9460: 9457: 9455: 9452: 9450: 9447: 9446: 9444: 9429: 9426: 9424: 9421: 9419: 9416: 9414: 9411: 9409: 9406: 9405: 9403: 9399: 9393: 9390: 9388: 9385: 9383: 9380: 9378: 9375: 9373: 9370: 9369: 9367: 9363: 9357: 9354: 9352: 9349: 9347: 9344: 9343: 9341: 9339: 9335: 9329: 9326: 9324: 9321: 9319: 9316: 9314: 9311: 9309: 9306: 9304: 9301: 9299: 9296: 9294: 9291: 9289: 9286: 9284: 9281: 9279: 9276: 9274: 9271: 9269: 9266: 9264: 9261: 9259: 9256: 9254: 9251: 9249: 9246: 9244: 9241: 9239: 9236: 9234: 9231: 9230: 9228: 9226: 9222: 9216: 9213: 9211: 9208: 9206: 9203: 9201: 9198: 9196: 9193: 9191: 9188: 9186: 9183: 9181: 9178: 9176: 9175:Methamidophos 9173: 9171: 9168: 9166: 9163: 9161: 9158: 9156: 9155:Fenpropathrin 9153: 9152: 9150: 9148: 9144: 9138: 9135: 9133: 9130: 9128: 9127:Ibotenic acid 9125: 9124: 9122: 9120: 9116: 9110: 9107: 9105: 9102: 9100: 9097: 9095: 9094:Oenanthotoxin 9092: 9090: 9087: 9085: 9082: 9080: 9077: 9075: 9072: 9070: 9067: 9065: 9062: 9060: 9057: 9055: 9052: 9050: 9047: 9046: 9044: 9042: 9038: 9032: 9029: 9027: 9024: 9022: 9019: 9017: 9014: 9013: 9011: 9009: 9005: 8999: 8998:Tetanospasmin 8996: 8994: 8991: 8990: 8988: 8986: 8982: 8976: 8973: 8971: 8968: 8966: 8963: 8961: 8958: 8956: 8953: 8951: 8948: 8946: 8943: 8941: 8938: 8936: 8933: 8931: 8928: 8926: 8923: 8921: 8920:Charybdotoxin 8918: 8916: 8913: 8911: 8908: 8906: 8903: 8901: 8900:Batrachotoxin 8898: 8897: 8895: 8893:Animal toxins 8891: 8887: 8880: 8875: 8873: 8868: 8866: 8861: 8860: 8857: 8845: 8842: 8840: 8837: 8835: 8832: 8829: 8828: 8825: 8819: 8816: 8814: 8811: 8809: 8806: 8804: 8801: 8799: 8796: 8794: 8791: 8789: 8786: 8784: 8781: 8779: 8776: 8773: 8769: 8766: 8764: 8761: 8759: 8756: 8755: 8753: 8749: 8743: 8739: 8729: 8726: 8724: 8721: 8719: 8716: 8714: 8711: 8709: 8706: 8704: 8701: 8699: 8696: 8694: 8691: 8689: 8686: 8684: 8681: 8679: 8676: 8674: 8671: 8669: 8666: 8664: 8661: 8659: 8656: 8654: 8651: 8649: 8646: 8644: 8641: 8639: 8636: 8634: 8631: 8629: 8628:Phencyclidine 8626: 8624: 8621: 8619: 8616: 8614: 8611: 8609: 8606: 8604: 8601: 8599: 8598:Nitrous oxide 8596: 8594: 8591: 8589: 8586: 8584: 8581: 8579: 8576: 8574: 8571: 8569: 8566: 8564: 8561: 8559: 8556: 8554: 8551: 8549: 8546: 8544: 8541: 8539: 8538:Levomethadone 8536: 8534: 8531: 8529: 8526: 8524: 8521: 8519: 8516: 8514: 8511: 8509: 8506: 8504: 8501: 8499: 8496: 8494: 8491: 8489: 8486: 8484: 8483:Hexafluronium 8481: 8479: 8476: 8474: 8471: 8469: 8466: 8464: 8461: 8459: 8456: 8454: 8451: 8449: 8446: 8444: 8441: 8439: 8436: 8434: 8431: 8429: 8426: 8424: 8421: 8419: 8416: 8414: 8411: 8409: 8406: 8404: 8401: 8399: 8396: 8394: 8391: 8389: 8386: 8384: 8381: 8379: 8376: 8374: 8373:Decamethonium 8371: 8369: 8366: 8364: 8361: 8359: 8356: 8354: 8351: 8349: 8346: 8344: 8343:Cisatracurium 8341: 8339: 8336: 8334: 8331: 8329: 8326: 8324: 8321: 8319: 8316: 8313: 8309: 8305: 8304:Bungarotoxins 8302: 8300: 8297: 8294: 8290: 8289:pentobarbital 8286: 8283: 8281: 8278: 8276: 8273: 8271: 8268: 8266: 8263: 8261: 8258: 8256: 8253: 8251: 8248: 8245: 8241: 8237: 8233: 8232:α-Neurotoxins 8230: 8228: 8225: 8223: 8220: 8219: 8217: 8211: 8204: 8200: 8194: 8191: 8189: 8186: 8184: 8181: 8179: 8176: 8174: 8171: 8169: 8166: 8164: 8161: 8159: 8156: 8154: 8151: 8149: 8146: 8144: 8141: 8139: 8136: 8134: 8131: 8129: 8126: 8124: 8121: 8119: 8116: 8114: 8111: 8109: 8106: 8104: 8101: 8099: 8096: 8094: 8091: 8089: 8086: 8084: 8081: 8079: 8076: 8074: 8071: 8069: 8066: 8064: 8061: 8059: 8056: 8054: 8051: 8049: 8046: 8044: 8041: 8039: 8036: 8033: 8029: 8026: 8024: 8021: 8019: 8016: 8014: 8011: 8009: 8006: 8004: 8001: 7999: 7996: 7994: 7991: 7989: 7986: 7984: 7981: 7979: 7976: 7974: 7971: 7969: 7966: 7964: 7961: 7959: 7956: 7954: 7951: 7949: 7946: 7944: 7941: 7939: 7936: 7934: 7933:Decamethonium 7931: 7929: 7926: 7924: 7921: 7919: 7916: 7914: 7911: 7909: 7906: 7904: 7901: 7899: 7896: 7894: 7891: 7889: 7886: 7884: 7881: 7879: 7876: 7874: 7871: 7869: 7868:Acetylcholine 7866: 7864: 7861: 7859: 7856: 7854: 7851: 7849: 7846: 7844: 7841: 7839: 7836: 7834: 7831: 7829: 7826: 7824: 7821: 7819: 7816: 7815: 7813: 7807: 7800: 7796: 7793: 7788: 7782: 7778: 7775: 7768: 7763: 7761: 7756: 7754: 7749: 7748: 7745: 7733: 7725: 7724: 7721: 7715: 7712: 7711: 7708: 7698: 7695: 7693: 7690: 7688: 7685: 7683: 7680: 7676: 7673: 7671: 7668: 7667: 7666: 7663: 7662: 7660: 7656: 7651: 7646: 7640: 7637: 7635: 7632: 7630: 7629:Samandaridine 7627: 7625: 7622: 7620: 7617: 7615: 7612: 7610: 7607: 7603: 7602:Marinobufagin 7600: 7598: 7595: 7593: 7590: 7588: 7585: 7583: 7580: 7579: 7578: 7575: 7573: 7572:Batrachotoxin 7570: 7568: 7565: 7564: 7562: 7558: 7553: 7547: 7544: 7542: 7539: 7538: 7536: 7532: 7527: 7524: 7520: 7516: 7506: 7503: 7501: 7498: 7496: 7493: 7491: 7488: 7486: 7483: 7482: 7480: 7476: 7471: 7465: 7462: 7460: 7457: 7455: 7452: 7450: 7447: 7445: 7442: 7440: 7437: 7433: 7430: 7429: 7428: 7425: 7424: 7422: 7418: 7413: 7407: 7404: 7402: 7399: 7397: 7394: 7392: 7389: 7387: 7384: 7382: 7379: 7377: 7374: 7372: 7369: 7367: 7364: 7362: 7359: 7357: 7354: 7352: 7349: 7347: 7344: 7342: 7339: 7337: 7334: 7332: 7329: 7327: 7326:Charybdotoxin 7324: 7322: 7319: 7318: 7316: 7312: 7307: 7304: 7300: 7296: 7290: 7287: 7283: 7280: 7278: 7275: 7274: 7273: 7270: 7268: 7265: 7263: 7260: 7258: 7255: 7253: 7250: 7248: 7245: 7243: 7240: 7238: 7237:Solauricidine 7235: 7233: 7230: 7228: 7225: 7223: 7220: 7218: 7215: 7213: 7210: 7208: 7205: 7203: 7200: 7198: 7195: 7193: 7190: 7188: 7185: 7183: 7182:Protoanemonin 7180: 7178: 7175: 7173: 7170: 7168: 7167:Oenanthotoxin 7165: 7163: 7160: 7158: 7155: 7153: 7150: 7148: 7145: 7143: 7140: 7138: 7135: 7133: 7130: 7128: 7125: 7123: 7120: 7118: 7115: 7113: 7110: 7108: 7105: 7103: 7100: 7098: 7095: 7093: 7090: 7088: 7085: 7083: 7080: 7078: 7075: 7074: 7072: 7069: 7065: 7059: 7056: 7054: 7051: 7049: 7046: 7044: 7043:Trichothecene 7041: 7039: 7036: 7034: 7031: 7029: 7026: 7024: 7021: 7019: 7016: 7014: 7011: 7009: 7006: 7004: 7003:Ibotenic acid 7001: 6999: 6996: 6993: 6989: 6985: 6981: 6978: 6976: 6973: 6971: 6968: 6966: 6963: 6961: 6958: 6955: 6951: 6947: 6946:beta-amanitin 6943: 6939: 6936: 6934: 6931: 6930: 6928: 6926: 6922: 6912: 6909: 6907: 6904: 6903: 6901: 6899: 6893: 6885: 6882: 6880: 6877: 6876: 6874: 6870: 6866: 6863: 6861: 6858: 6857: 6856: 6854: 6850: 6846: 6843: 6842: 6841: 6838: 6837: 6835: 6833: 6829: 6817: 6813: 6810: 6809: 6808: 6807: 6803: 6799: 6796: 6795: 6794: 6793: 6789: 6785: 6782: 6781: 6780: 6779: 6775: 6774: 6772: 6770: 6766: 6760: 6757: 6755: 6752: 6750: 6747: 6745: 6741: 6740:Cholera toxin 6738: 6736: 6734: 6730: 6727: 6724: 6723: 6721: 6719: 6713: 6703: 6700: 6698: 6695: 6694: 6692: 6690: 6686: 6676: 6673: 6671: 6668: 6666: 6663: 6661: 6657: 6653: 6650: 6649: 6647: 6644: 6639: 6631: 6628: 6627: 6626: 6623: 6621: 6618: 6617: 6614: 6611: 6609: 6605: 6595: 6592: 6590: 6589:Anthrax toxin 6587: 6586: 6584: 6578: 6570: 6567: 6566: 6565: 6564: 6560: 6556: 6553: 6551: 6548: 6547: 6546: 6545: 6541: 6537: 6534: 6532: 6529: 6528: 6527: 6526: 6522: 6518: 6515: 6513: 6512:Tetanospasmin 6510: 6509: 6508: 6507: 6503: 6502: 6500: 6496: 6491: 6488: 6486: 6482: 6479: 6477: 6471: 6468: 6466: 6462: 6459: 6457: 6451: 6443: 6440: 6438: 6435: 6433: 6430: 6428: 6425: 6423: 6420: 6418: 6415: 6413: 6410: 6409: 6408: 6405: 6404: 6399: 6394: 6392: 6387: 6385: 6380: 6379: 6376: 6360: 6358: 6355: 6354: 6352: 6349: 6346: 6343: 6341: 6338: 6337: 6333: 6327: 6324: 6322: 6319: 6317: 6314: 6312: 6309: 6307: 6304: 6302: 6299: 6297: 6294: 6292: 6289: 6287: 6284: 6282: 6279: 6277: 6274: 6272: 6269: 6267: 6264: 6262: 6259: 6258: 6256: 6252: 6246: 6243: 6241: 6240:Methocarbamol 6238: 6236: 6235:Mephenoxalone 6233: 6231: 6228: 6226: 6225:Chlorzoxazone 6223: 6221: 6218: 6217: 6215: 6213: 6209: 6199: 6196: 6195: 6193: 6191: 6187: 6181: 6178: 6176: 6173: 6171: 6168: 6161: 6160: 6156: 6155:amitriptyline 6152: 6149: 6147: 6144: 6142: 6139: 6136: 6132: 6128: 6125: 6123: 6120: 6118: 6117:Carbamazepine 6115: 6114: 6112: 6110: 6106: 6100: 6097: 6095: 6092: 6090: 6087: 6085: 6082: 6080: 6077: 6075: 6072: 6070: 6067: 6066: 6064: 6062: 6058: 6055: 6053: 6047: 6041: 6038: 6036: 6033: 6031: 6028: 6026: 6023: 6021: 6018: 6017: 6015: 6013: 6009: 5999: 5996: 5994: 5991: 5989: 5986: 5984: 5981: 5979: 5976: 5974: 5971: 5970: 5968: 5964: 5957: 5950: 5947: 5945: 5942: 5940: 5937: 5935: 5932: 5930: 5927: 5925: 5922: 5921: 5919: 5917: 5913: 5906: 5899: 5896: 5894: 5891: 5889: 5886: 5884: 5881: 5879: 5876: 5874: 5871: 5869: 5866: 5864: 5861: 5859: 5856: 5854: 5851: 5849: 5846: 5844: 5841: 5839: 5836: 5834: 5831: 5829: 5826: 5824: 5821: 5819: 5816: 5813: 5809: 5806: 5805: 5803: 5801: 5797: 5791: 5788: 5786: 5783: 5781: 5778: 5776: 5773: 5772: 5770: 5768: 5764: 5758: 5755: 5753: 5750: 5748: 5745: 5743: 5740: 5738: 5735: 5732: 5725: 5722: 5721: 5719: 5717: 5713: 5707: 5704: 5702: 5699: 5697: 5694: 5692: 5689: 5686: 5679: 5676: 5674: 5671: 5669: 5666: 5664: 5661: 5659: 5656: 5655: 5653: 5649: 5643: 5640: 5638: 5635: 5633: 5630: 5628: 5625: 5623: 5620: 5619: 5617: 5613: 5607: 5604: 5602: 5599: 5597: 5594: 5592: 5589: 5587: 5584: 5582: 5579: 5576: 5575:Dexketoprofen 5569: 5566: 5563: 5555: 5548: 5545: 5543: 5540: 5538: 5535: 5533: 5530: 5529: 5527: 5523: 5520: 5518: 5514: 5508: 5505: 5503: 5500: 5498: 5495: 5491: 5488: 5486: 5483: 5481: 5478: 5476: 5473: 5471: 5468: 5466: 5463: 5461: 5458: 5456: 5453: 5452: 5451: 5448: 5446: 5443: 5441: 5438: 5436: 5433: 5432: 5430: 5427: 5423: 5413: 5410: 5407: 5403: 5396: 5393: 5391: 5388: 5386: 5383: 5381: 5378: 5376: 5373: 5371: 5368: 5366: 5363: 5361: 5358: 5356: 5353: 5351: 5350:Phenoperidine 5348: 5346: 5343: 5341: 5338: 5336: 5333: 5331: 5328: 5326: 5323: 5321: 5318: 5316: 5313: 5311: 5308: 5306: 5303: 5301: 5298: 5296: 5293: 5290: 5286: 5283: 5281: 5280:Ethoheptazine 5278: 5276: 5273: 5271: 5268: 5266: 5263: 5261: 5258: 5256: 5253: 5251: 5248: 5246: 5243: 5241: 5238: 5236: 5233: 5231: 5228: 5227: 5225: 5221: 5215: 5212: 5210: 5207: 5205: 5202: 5199: 5195: 5191: 5187: 5183: 5176: 5173: 5171: 5168: 5166: 5163: 5161: 5158: 5156: 5153: 5151: 5148: 5146: 5143: 5141: 5140:Hydromorphone 5138: 5136: 5133: 5130: 5126: 5122: 5115: 5112: 5110: 5109:Ethylmorphine 5107: 5105: 5102: 5100: 5097: 5094: 5087: 5084: 5082: 5079: 5077: 5074: 5072: 5069: 5066: 5059: 5058:Buprenorphine 5056: 5054: 5051: 5049: 5046: 5045: 5043: 5041:Semisynthetic 5039: 5033: 5030: 5028: 5025: 5023: 5020: 5017: 5013: 5010: 5006: 5003: 5001: 4998: 4997: 4996: 4993: 4992: 4990: 4988: 4984: 4980: 4977: 4975: 4971: 4966: 4962: 4958: 4951: 4946: 4944: 4939: 4937: 4932: 4931: 4928: 4918: 4914: 4909: 4903: 4900: 4898: 4895: 4893: 4890: 4888: 4885: 4883: 4882:Thiopropamine 4880: 4878: 4875: 4873: 4870: 4868: 4865: 4863: 4860: 4858: 4855: 4853: 4850: 4848: 4845: 4843: 4840: 4838: 4835: 4833: 4830: 4828: 4825: 4823: 4820: 4818: 4815: 4813: 4810: 4808: 4805: 4803: 4800: 4798: 4795: 4793: 4790: 4788: 4785: 4783: 4782:Meclofenoxate 4780: 4778: 4775: 4773: 4770: 4768: 4765: 4763: 4760: 4758: 4755: 4753: 4750: 4748: 4745: 4743: 4740: 4738: 4735: 4733: 4732:Hexacyclonate 4730: 4728: 4725: 4723: 4720: 4718: 4715: 4713: 4710: 4708: 4705: 4703: 4700: 4698: 4695: 4693: 4690: 4688: 4685: 4683: 4680: 4678: 4675: 4673: 4670: 4668: 4665: 4663: 4660: 4658: 4655: 4653: 4650: 4648: 4647:Centanafadine 4645: 4643: 4640: 4638: 4635: 4633: 4630: 4628: 4625: 4623: 4620: 4618: 4615: 4613: 4610: 4608: 4605: 4603: 4600: 4598: 4595: 4593: 4590: 4589: 4587: 4583: 4577: 4574: 4572: 4569: 4567: 4564: 4562: 4559: 4557: 4554: 4552: 4549: 4547: 4544: 4542: 4539: 4537: 4534: 4532: 4529: 4527: 4524: 4522: 4519: 4518: 4516: 4514: 4510: 4504: 4501: 4499: 4496: 4494: 4491: 4489: 4486: 4484: 4481: 4479: 4476: 4474: 4471: 4469: 4466: 4464: 4461: 4459: 4456: 4454: 4451: 4449: 4446: 4444: 4441: 4439: 4436: 4434: 4431: 4429: 4426: 4424: 4421: 4419: 4416: 4414: 4411: 4409: 4406: 4404: 4401: 4399: 4396: 4394: 4391: 4389: 4386: 4384: 4383:Ioflupane (I) 4381: 4379: 4376: 4374: 4371: 4369: 4366: 4364: 4361: 4359: 4356: 4354: 4351: 4349: 4346: 4344: 4341: 4339: 4336: 4334: 4331: 4329: 4326: 4324: 4321: 4320: 4318: 4316: 4312: 4306: 4303: 4301: 4298: 4296: 4293: 4292: 4290: 4288: 4284: 4278: 4275: 4273: 4270: 4268: 4265: 4263: 4260: 4258: 4255: 4253: 4250: 4248: 4245: 4243: 4240: 4238: 4235: 4233: 4230: 4228: 4225: 4223: 4220: 4218: 4215: 4213: 4210: 4208: 4205: 4203: 4200: 4198: 4195: 4193: 4190: 4188: 4185: 4183: 4180: 4178: 4175: 4173: 4170: 4168: 4165: 4163: 4160: 4158: 4155: 4153: 4150: 4148: 4145: 4143: 4140: 4138: 4135: 4134: 4132: 4130: 4126: 4120: 4117: 4115: 4112: 4110: 4107: 4105: 4102: 4100: 4099:Phacetoperane 4097: 4095: 4092: 4089: 4085: 4082: 4080: 4077: 4075: 4072: 4070: 4067: 4065: 4062: 4060: 4057: 4055: 4052: 4050: 4047: 4045: 4042: 4040: 4037: 4035: 4032: 4030: 4027: 4025: 4022: 4020: 4017: 4015: 4012: 4010: 4007: 4006: 4004: 4002: 3998: 3992: 3989: 3987: 3984: 3982: 3979: 3977: 3974: 3972: 3969: 3967: 3964: 3962: 3959: 3957: 3954: 3952: 3949: 3947: 3944: 3942: 3939: 3937: 3934: 3932: 3929: 3927: 3924: 3922: 3919: 3918: 3916: 3914: 3910: 3904: 3901: 3899: 3896: 3894: 3891: 3889: 3888:Phenmetrazine 3886: 3884: 3881: 3879: 3876: 3874: 3871: 3869: 3866: 3864: 3861: 3859: 3856: 3854: 3851: 3849: 3846: 3844: 3841: 3839: 3836: 3835: 3833: 3831: 3827: 3821: 3818: 3816: 3815:Xylopropamine 3813: 3811: 3808: 3806: 3803: 3801: 3798: 3796: 3793: 3791: 3790:Theodrenaline 3788: 3786: 3783: 3781: 3778: 3776: 3773: 3770: 3766: 3763: 3761: 3758: 3756: 3753: 3751: 3748: 3746: 3743: 3741: 3738: 3736: 3733: 3731: 3728: 3726: 3723: 3721: 3718: 3716: 3713: 3711: 3708: 3706: 3705:Phenylephrine 3703: 3701: 3700:Phenylalanine 3698: 3696: 3693: 3691: 3688: 3686: 3683: 3681: 3678: 3676: 3673: 3671: 3668: 3666: 3663: 3661: 3658: 3656: 3653: 3651: 3648: 3646: 3643: 3641: 3640:Orciprenaline 3638: 3636: 3633: 3631: 3625: 3623: 3620: 3618: 3615: 3613: 3610: 3608: 3605: 3603: 3600: 3598: 3595: 3593: 3590: 3588: 3585: 3583: 3580: 3578: 3575: 3573: 3570: 3568: 3565: 3563: 3560: 3558: 3555: 3553: 3550: 3548: 3545: 3542: 3538: 3534: 3531: 3529: 3526: 3524: 3521: 3519: 3516: 3514: 3513:Mephentermine 3511: 3509: 3506: 3504: 3501: 3499: 3496: 3494: 3491: 3489: 3486: 3484: 3481: 3479: 3476: 3474: 3471: 3469: 3466: 3464: 3461: 3459: 3456: 3454: 3451: 3449: 3446: 3443: 3437: 3435: 3432: 3430: 3427: 3425: 3422: 3420: 3417: 3415: 3412: 3410: 3407: 3405: 3402: 3400: 3397: 3395: 3392: 3390: 3387: 3385: 3382: 3380: 3377: 3375: 3372: 3370: 3367: 3365: 3362: 3360: 3357: 3354: 3350: 3346: 3343: 3341: 3338: 3336: 3333: 3331: 3328: 3326: 3323: 3321: 3318: 3316: 3313: 3311: 3308: 3306: 3303: 3301: 3298: 3296: 3293: 3291: 3288: 3286: 3283: 3281: 3278: 3276: 3273: 3271: 3268: 3265: 3261: 3257: 3254: 3252: 3249: 3247: 3244: 3242: 3239: 3237: 3234: 3232: 3226: 3224: 3221: 3219: 3216: 3214: 3211: 3209: 3206: 3204: 3201: 3199: 3196: 3194: 3191: 3189: 3186: 3184: 3181: 3179: 3176: 3174: 3171: 3169: 3166: 3164: 3161: 3159: 3156: 3154: 3153:Benzphetamine 3151: 3149: 3146: 3144: 3141: 3139: 3136: 3134: 3131: 3129: 3126: 3123: 3119: 3115: 3112: 3110: 3107: 3105: 3102: 3100: 3097: 3095: 3094:2-Aminoindane 3092: 3090: 3087: 3085: 3082: 3080: 3077: 3075: 3072: 3070: 3067: 3065: 3062: 3060: 3057: 3055: 3052: 3050: 3047: 3045: 3042: 3040: 3037: 3035: 3032: 3030: 3027: 3025: 3022: 3020: 3017: 3015: 3012: 3010: 3007: 3005: 3002: 3000: 2997: 2995: 2992: 2990: 2987: 2985: 2982: 2980: 2977: 2975: 2972: 2971: 2969: 2967: 2963: 2957: 2954: 2952: 2949: 2947: 2944: 2942: 2939: 2937: 2934: 2932: 2929: 2927: 2924: 2922: 2919: 2918: 2916: 2914: 2910: 2904: 2901: 2899: 2896: 2894: 2891: 2889: 2886: 2884: 2881: 2879: 2876: 2875: 2873: 2871: 2867: 2861: 2858: 2856: 2853: 2851: 2848: 2846: 2843: 2841: 2838: 2836: 2833: 2831: 2828: 2826: 2823: 2821: 2818: 2817: 2815: 2813: 2809: 2803: 2800: 2798: 2795: 2793: 2790: 2788: 2785: 2783: 2780: 2778: 2775: 2773: 2770: 2768: 2765: 2763: 2760: 2758: 2755: 2753: 2750: 2748: 2745: 2743: 2740: 2738: 2735: 2733: 2730: 2728: 2725: 2723: 2720: 2718: 2715: 2713: 2710: 2708: 2705: 2703: 2700: 2698: 2695: 2693: 2690: 2688: 2685: 2683: 2680: 2678: 2675: 2673: 2670: 2668: 2665: 2663: 2660: 2658: 2655: 2653: 2650: 2648: 2645: 2644: 2642: 2640: 2636: 2630: 2627: 2625: 2622: 2620: 2617: 2615: 2612: 2610: 2607: 2605: 2602: 2600: 2597: 2595: 2592: 2590: 2587: 2585: 2584:Methcathinone 2582: 2580: 2577: 2575: 2572: 2570: 2567: 2565: 2562: 2560: 2557: 2555: 2552: 2550: 2547: 2545: 2542: 2540: 2537: 2535: 2532: 2530: 2527: 2525: 2522: 2520: 2517: 2515: 2512: 2510: 2507: 2505: 2502: 2500: 2497: 2495: 2492: 2490: 2487: 2485: 2482: 2480: 2477: 2476: 2474: 2472: 2468: 2462: 2459: 2457: 2454: 2452: 2449: 2447: 2444: 2443: 2441: 2439: 2435: 2429: 2426: 2424: 2423:Tenocyclidine 2421: 2419: 2418:Rolicyclidine 2416: 2414: 2413:Phencyclidine 2411: 2409: 2408:Phencyclamine 2406: 2404: 2401: 2399: 2396: 2394: 2391: 2389: 2386: 2384: 2381: 2379: 2378:Benocyclidine 2376: 2375: 2373: 2371: 2367: 2361: 2358: 2356: 2353: 2351: 2348: 2346: 2343: 2341: 2338: 2336: 2333: 2331: 2328: 2326: 2323: 2321: 2318: 2316: 2313: 2311: 2308: 2306: 2303: 2301: 2298: 2296: 2293: 2292: 2290: 2288: 2284: 2278: 2275: 2273: 2270: 2268: 2265: 2263: 2260: 2258: 2255: 2253: 2252:Isometheptene 2250: 2248: 2245: 2243: 2240: 2238: 2235: 2233: 2230: 2229: 2227: 2225: 2221: 2215: 2212: 2210: 2207: 2205: 2202: 2200: 2197: 2195: 2192: 2190: 2187: 2185: 2182: 2180: 2177: 2175: 2174:Aminophylline 2172: 2170: 2167: 2165: 2162: 2160: 2157: 2156: 2154: 2152: 2148: 2142: 2139: 2137: 2134: 2132: 2129: 2127: 2124: 2122: 2119: 2118: 2116: 2114: 2110: 2106: 2099: 2094: 2092: 2087: 2085: 2080: 2079: 2076: 2070: 2067: 2066: 2054: 2050: 2045: 2040: 2036: 2032: 2028: 2024: 2020: 2013: 2005: 2001: 1997: 1993: 1989: 1985: 1981: 1977: 1970: 1962: 1958: 1954: 1950: 1946: 1942: 1938: 1934: 1927: 1919: 1915: 1911: 1907: 1903: 1899: 1892: 1884: 1880: 1876: 1872: 1865: 1857: 1853: 1849: 1845: 1840: 1835: 1831: 1827: 1823: 1816: 1808: 1804: 1800: 1796: 1789: 1787: 1778: 1777:The Scientist 1774: 1767: 1759: 1755: 1751: 1745: 1741: 1737: 1733: 1729: 1722: 1714: 1710: 1705: 1700: 1696: 1692: 1688: 1681: 1673: 1669: 1664: 1659: 1655: 1651: 1647: 1640: 1632: 1628: 1624: 1620: 1616: 1609: 1607: 1605: 1596: 1592: 1588: 1584: 1580: 1576: 1569: 1561: 1557: 1553: 1549: 1545: 1541: 1533: 1525: 1521: 1517: 1513: 1509: 1505: 1497: 1489: 1485: 1481: 1477: 1473: 1469: 1461: 1453: 1449: 1444: 1439: 1435: 1431: 1427: 1423: 1415: 1400: 1396: 1395:"Epibatidine" 1390: 1375: 1369: 1361: 1357: 1353: 1352:"Epibatidine" 1346: 1344: 1335: 1331: 1327: 1323: 1316: 1308: 1304: 1300: 1296: 1289: 1282:(7): 449–460. 1281: 1277: 1270: 1268: 1259: 1255: 1251: 1247: 1240: 1238: 1229: 1225: 1220: 1215: 1211: 1207: 1203: 1196: 1194: 1192: 1190: 1188: 1179: 1175: 1171: 1167: 1163: 1159: 1152: 1144: 1140: 1136: 1132: 1128: 1121: 1113: 1109: 1105: 1101: 1097: 1093: 1089: 1082: 1073: 1068: 1064: 1060: 1056: 1049: 1041: 1037: 1033: 1029: 1025: 1021: 1017: 1010: 1008: 1006: 990: 988: 979: 971: 964: 956: 952: 948: 944: 937: 930: 928: 926: 917: 913: 908: 903: 899: 895: 891: 887: 883: 876: 872: 863: 860: 858: 857:Phantasmidine 855: 853: 849: 846: 843: 839: 838:Batrachotoxin 836: 834: 831: 829: 826: 825: 819: 817: 807: 805: 801: 796: 794: 791:and muscular 790: 786: 782: 778: 774: 764: 761: 759: 749: 746: 742: 737: 731: 723: 718: 715: 705: 702: 697: 694: 692: 688: 683: 681: 677: 673: 669: 665: 661: 657: 653: 647: 645: 641: 637: 633: 629: 625: 621: 606: 604: 600: 596: 592: 582: 580: 576: 572: 568: 564: 554: 549: 544: 540: 538: 534: 529: 527: 521: 513: 509: 506: 502: 494: 490: 486: 484: 479: 475: 465: 463: 459: 455: 450: 447: 443: 442: 437: 433: 432: 427: 423: 419: 409: 402: 396: 387: 382: 381: 378: 371: 362: 361: 358: 351: 347: 345: 341: 334: 330: 329: 327: 324: 319: 312: 310: 306: 282: 280: 276: 271: 267: 263: 260: 258: 256:ECHA InfoCard 252: 245: 241: 240: 238: 236: 232: 225: 221: 220: 218: 216: 212: 205: 201: 200: 198: 196: 192: 185: 181: 180: 178: 176: 172: 165: 161: 160: 158: 156: 152: 145: 141: 140: 138: 136: 132: 125: 121: 120: 118: 111: 107: 100: 96: 95: 93: 91: 87: 79: 75: 71: 66: 65: 62: 55: 50: 46: 41: 37: 32: 22: 9225:Nerve agents 9041:Plant toxins 8964: 8955:Vanillotoxin 8950:Tetrodotoxin 8915:Bungarotoxin 8713:Tubocurarine 8643:Promegestone 8638:Progesterone 8553:Mecamylamine 8363:Cyclopropane 8353:Coronaridine 8285:Barbiturates 8270:Anatruxonium 8240:α-cobratoxin 8083:Sazetidine A 8003:JNJ-39393406 7993:Ispronicline 7952: 7713: 7692:Calcicludine 7682:Calciseptine 7665:Bungarotoxin 7634:Tarichatoxin 7608: 7582:Arenobufagin 7546:Tetrodotoxin 7505:Tetrodotoxin 7459:Vanillotoxin 7396:Phaiodotoxin 7299:Invertebrate 7222:Solasodamine 7157:Lotaustralin 6992:Fumonisin B4 6988:Fumonisin B2 6984:Fumonisin B1 6970:Cytochalasin 6872: 6852: 6804: 6790: 6784:Superantigen 6776: 6732: 6620:Streptolysin 6561: 6542: 6523: 6504: 6245:Orphenadrine 6220:Carisoprodol 6212:Myorelaxants 6162: 6012:Cannabinoids 5978:Floctafenine 5883:Salicylamide 5562:+paracetamol 5554:Dexibuprofen 5542:Flurbiprofen 5532:Benoxaprofen 5507:Propacetamol 5497:Parapropamol 5465:+hydrocodone 5406:+paracetamol 5375:Remifentanil 5365:Proheptazine 5295:Ketobemidone 5235:Alphaprodine 5182:+paracetamol 5170:Nicomorphine 5165:Nicodicodine 5121:+paracetamol 5093:+paracetamol 5076:Desomorphine 5005:+paracetamol 4837:Oxaprotiline 4787:Medifoxamine 4707:Fenpentadiol 4687:Dimethocaine 4682:Diclofensine 4662:Cropropamide 4657:Clofenciclan 4612:Amiphenazole 4566:7-Methyl-αET 4561:6-Fluoro-αMT 4541:5-Fluoro-αMT 4536:5-Chloro-αMT 4531:4-Methyl-αMT 4526:4-Methyl-αET 4368:Difluoropine 4353:Cocaethylene 4338:Brasofensine 4277:Pyrovalerone 4129:Pyrrolidines 3848:Fenmetramide 3843:Fenbutrazate 3820:Zylofuramine 3780:Solriamfetol 3612:Norfenefrine 3518:Metanephrine 3444:(Selegiline) 3434:Isoprenaline 3364:Feprosidnine 3345:Fenfluramine 3340:Fenethylline 3325:Famprofazone 3198:Cinnamedrine 3128:Amphetaminil 3079:Amfepentorex 2757:Sazetidine A 2722:Ispronicline 2706: 2687:Bradanicline 2639:Cholinergics 2554:Ethcathinone 2438:Benzazepines 2393:Eticyclidine 2214:Theophylline 2199:Paraxanthine 2026: 2022: 2012: 1979: 1975: 1969: 1936: 1932: 1926: 1901: 1897: 1891: 1877:(1): 21–39. 1874: 1870: 1864: 1829: 1825: 1815: 1801:(4): 563–9. 1798: 1794: 1776: 1766: 1731: 1727: 1721: 1694: 1690: 1680: 1656:(1): 69–76. 1653: 1649: 1639: 1622: 1618: 1578: 1574: 1568: 1543: 1539: 1532: 1507: 1503: 1496: 1471: 1467: 1460: 1425: 1421: 1414: 1403:. Retrieved 1398: 1389: 1378:. Retrieved 1368: 1360:the original 1355: 1325: 1321: 1315: 1298: 1294: 1288: 1279: 1275: 1249: 1245: 1212:(1): 69–76. 1209: 1205: 1161: 1157: 1151: 1134: 1130: 1120: 1095: 1091: 1081: 1062: 1058: 1048: 1023: 1019: 993:. Retrieved 986: 978: 969: 963: 946: 943:Heterocycles 942: 889: 885: 875: 862:Tetrodotoxin 848:Nemertelline 833:Arrow poison 816:mecamylamine 813: 797: 785:hypertension 770: 762: 755: 752:Pharmacology 741:hypertension 738: 711: 698: 695: 684: 648: 640:α7 receptors 622:(nAChR) or 617: 588: 560: 552: 530: 522: 519: 510: 500: 498: 492: 477: 474:John W. Daly 471: 451: 446:John W. Daly 439: 429: 417: 416: 405:   399:   244:ChEMBL298826 77: 73: 69: 21:Eptifibatide 9479:Neurotoxins 9377:Catecholine 9318:Fluorotabun 9165:Bromethalin 9109:Veratridine 9084:Ginkgotoxin 9054:Bicuculline 9008:Cyanotoxins 8975:Dendrotoxin 8965:Epibatidine 8940:Poneratoxin 8886:Neurotoxins 8818:Pirisudanol 8783:Cyprodenate 8763:Adafenoxate 8678:Surugatoxin 8668:Sevoflurane 8623:Pentolinium 8603:Norketamine 8523:Laudanosine 8453:Erythravine 8443:Encenicline 8428:Dipyrandium 8398:Dextrorphan 8244:α-conotoxin 8203:Antagonists 8188:WAY-317,538 8183:Varenicline 8173:Tropisetron 8163:Tebanicline 8108:SSR-180,711 8073:Rivanicline 8063:Pozanicline 8058:PNU-282,987 8053:PNU-120,596 8048:PHA-709,829 8043:PHA-543,613 7983:Galantamine 7958:Epiboxidine 7953:Epibatidine 7873:Altinicline 7655:Snake venom 7609:Epibatidine 7597:Cinobufagin 7454:Stromatoxin 7401:Imperatoxin 7351:Scyllatoxin 7257:Tagetitoxin 7252:Swainsonine 7242:Solauricine 7207:Solamargine 7202:Scopolamine 7192:Retronecine 7058:Zearalenone 6726:Shiga toxin 6697:Cord factor 6536:Enterotoxin 6531:Alpha toxin 6525:perfringens 6517:Tetanolysin 6495:Clostridium 6432:hepatotoxin 6422:enterotoxin 6412:cardiotoxin 6347:from market 6291:Frunevetmab 6271:Bedinvetmab 6180:PF-05089771 6089:Mirogabalin 6050:Ion channel 6020:Cannabidiol 5973:Benzydamine 5916:Pyrazolones 5898:Wintergreen 5848:Ethenzamide 5843:Dipyrocetyl 5800:Salicylates 5742:Lumiracoxib 5678:Indometacin 5606:Zaltoprofen 5525:Propionates 5435:Acetanilide 5426:Paracetamol 5360:Piritramide 5345:Phenazocine 5340:Phenadoxone 5330:Pentazocine 5325:Oliceridine 5320:Norpipanone 5289:+fluanisone 5270:Dimenoxadol 5250:Carfentanil 5245:Bezitramide 5240:Anileridine 5209:Papaveretum 5204:Oxymorphone 5198:+naltrexone 5160:Nicocodeine 5145:Levorphanol 5114:Hydrocodone 5071:Butorphanol 5016:+naltrexone 4887:Thiothinone 4872:Tametraline 4857:Rauwolscine 4827:Nomifensine 4822:Nikethamide 4767:Lomevactone 4752:JNJ-7925476 4747:Indatraline 4722:GSK1360707F 4677:Desipramine 4667:Crotetamide 4652:Ciclazindol 4632:Benzydamine 4622:Atomoxetine 4617:Atipamezole 4513:Tryptamines 4483:Tesofensine 4049:Difemetorex 4001:Piperidines 3913:Piperazines 3775:Sibutramine 3745:Prenylamine 3695:Phentermine 3650:Oxifentorex 3547:Methoxamine 3523:Metaraminol 3359:Fenproporex 3330:Fencamfamin 3295:Epinephrine 3218:Clortermine 3208:Clobenzorex 3203:Clenbuterol 3178:Camfetamine 3114:Amphetamine 3084:Amidephrine 2956:Thozalinone 2936:Cyclazodone 2883:Armodafinil 2845:Pentetrazol 2825:Bicuculline 2812:Convulsants 2802:WAY-317,538 2797:Varenicline 2787:Tebanicline 2767:SSR-180,711 2752:Rivanicline 2747:Pozanicline 2742:PNU-282,987 2737:PNU-120,596 2732:PHA-543,613 2712:Epiboxidine 2707:Epibatidine 2672:Altinicline 2564:Flephedrone 2519:Amfepramone 2398:Gacyclidine 2242:Cyprodenate 2224:Alkylamines 2209:Theobromine 2141:Rimantadine 2113:Adamantanes 1164:(1): 1–26. 852:nicotelline 789:bradycardia 777:habituation 745:respiratory 717:sympathetic 701:enantiomers 674:as well as 599:hygroscopic 579:epiboxidine 501:E. anthonyi 418:Epibatidine 316: g·mol 262:100.162.281 99:140111-52-0 52:Identifiers 28:Epibatidine 9449:Analgesics 9443:Categories 9323:Chinese VX 9233:Cyclosarin 9180:Endosulfan 9147:Pesticides 9119:Mycotoxins 9069:Strychnine 9064:Picrotoxin 9059:Penitrem A 9021:Guanitoxin 9016:Anatoxin-a 8935:Huwentoxin 8930:Fasciculin 8778:Citicoline 8758:Acetyl-coA 8742:Precursors 8718:Vanoxerine 8708:Tropeinium 8693:Toxiferine 8658:Reboxetine 8648:Radafaxine 8593:Neramexane 8583:Mivacurium 8578:Metocurine 8543:Malouetine 8508:Isoflurane 8463:Fazadinium 8458:Esketamine 8438:Doxacurium 8423:Dioscorine 8383:Desflurane 8348:Coclaurine 8280:Atracurium 8265:Amantadine 8255:Alcuronium 8008:Levamisole 7998:Ivermectin 7943:Dianicline 7903:Butinoline 7888:Anatoxin-a 7777:modulators 7687:Taicatoxin 7624:Samandarin 7577:Bufotoxins 7541:Ciguatoxin 7519:Vertebrate 7464:Huwentoxin 7444:Cupiennins 7427:Latrotoxin 7371:Kaliotoxin 7341:Margatoxin 7331:Maurotoxin 7272:Toxalbumin 7262:Tinyatoxin 7247:Strychnine 7232:Solasonine 7227:Solasodine 7212:Solanidine 7132:Falcarinol 7117:Delphinine 7033:Phalloidin 7023:Ochratoxin 7018:Orellanine 7008:Lolitrem B 6975:Ergotamine 6925:Mycotoxins 6769:Mechanisms 6728:/Verotoxin 6665:Exfoliatin 6625:Leukocidin 6442:phototoxin 6437:neurotoxin 6321:Rimazolium 6316:Proglumide 6261:Analgecine 6198:Flupirtine 6141:Mexiletine 6122:Lacosamide 6099:Ziconotide 6094:Pregabalin 6084:Leconotide 6074:Gabapentin 6052:modulators 6035:Nabiximols 5998:Proquazone 5993:Nimesulide 5988:Nabumetone 5939:Nifenazone 5853:Guacetisal 5838:Diflunisal 5823:Benorylate 5757:Valdecoxib 5737:Etoricoxib 5668:Diclofenac 5658:Acemetacin 5627:Lornoxicam 5581:Loxoprofen 5568:Ketoprofen 5537:Fenoprofen 5502:Phenacetin 5480:+oxycodone 5470:+ibuprofen 5402:+celecoxib 5385:Tapentadol 5380:Sufentanil 5355:Piminodine 5305:Meptazinol 5300:Lofentanil 5275:Dipipanone 5230:Alfentanil 5190:+ibuprofen 5155:Nalbuphine 5125:+ibuprofen 4957:Analgesics 4867:Setazindol 4852:Rasagiline 4842:PNU-99,194 4792:Mefexamide 4762:Leptacline 4757:Lazabemide 4727:GYKI-52895 4717:Gilutensin 4642:BTS 74,398 4607:Amineptine 4556:5-MeO-DIPT 4388:Norcocaine 4378:FP-β-CPPIT 4373:FE-β-CPPIT 4295:Oxiracetam 4272:Prolintane 3991:Vanoxerine 3903:Radafaxine 3878:PD-128,907 3873:Oxaflozane 3858:Manifaxine 3785:Synephrine 3765:Salbutamol 3760:Ropinirole 3715:Pholedrine 3655:Oxilofrine 3645:Ortetamine 3635:Octopamine 3602:Nisoxetine 3458:Lophophine 3448:Lefetamine 3429:Isoetarine 3424:Iofetamine 3389:Hexapradol 3379:Furfenorex 3374:Formetorex 3320:Etilefrine 3305:Etafedrine 3275:Dopexamine 3260:Dextrodopa 3251:Dobutamine 3236:Denopamine 3223:Cypenamine 3193:Cilobamine 3148:Benfluorex 3133:Arbutamine 3074:Amfecloral 3064:Alfetamine 2946:Fluminorex 2941:Fenozolone 2931:Clominorex 2913:Oxazolines 2893:CRL-40,941 2888:CRL-40,940 2855:Strychnine 2850:Picrotoxin 2820:Anatoxin-a 2702:Dianicline 2619:Pentedrone 2589:Methedrone 2579:Mephedrone 2529:Buphedrone 2524:Benzedrone 2471:Cathinones 2428:Tiletamine 2388:Esketamine 2330:LY-503,430 2325:LY-404,187 2247:Heptaminol 2237:Cypenamine 2189:Dimethazan 2131:Bromantane 2126:Amantadine 2121:Adapromine 2105:Stimulants 1443:2434/59291 1405:2021-11-12 1380:2014-03-12 1059:BioScience 995:2015-05-06 868:References 714:splanchnic 597:. It is a 321:3D model ( 309:Molar mass 224:CHEBI:4803 184:M6K314F1XX 155:ChemSpider 90:CAS Number 61:IUPAC name 9170:Crimidine 9132:Muscarine 9104:Volkensin 9089:Cicutoxin 9049:Aconitine 9031:Saxitoxin 8985:Bacterial 8945:Saxitoxin 8925:Conotoxin 8618:Pentamine 8613:Pempidine 8563:Methadone 8558:Memantine 8478:Halothane 8468:Gallamine 8448:Enflurane 8403:Diadonium 8318:Bupropion 8103:SIB-1553A 8098:SIB-1508Y 8088:SB-206553 7913:Carbachol 7893:AR-R17779 7883:Anatabine 7878:Anabasine 7843:A-867,744 7838:A-582,941 7833:A-366,833 7592:Bufotenin 7587:Bufotalin 7557:Amphibian 7500:Saxitoxin 7490:Eledoisin 7485:Conotoxin 7356:Hefutoxin 7172:Oleandrin 7152:Linamarin 7142:Helenalin 7102:Cicutoxin 7097:Chaconine 7077:Amygdalin 7048:Vomitoxin 6998:Gliotoxin 6980:Fumonisin 6933:Aflatoxin 6896:Virulence 6832:Endotoxin 6563:botulinum 6544:difficile 6454:Bacterial 6427:hemotoxin 6417:cytotoxin 6357:Phase III 6345:Withdrawn 6326:Tanezumab 6286:Clonidine 6281:Capsaicin 6135:lidocaine 5983:Glafenine 5944:Phenazone 5888:Salsalate 5818:Aloxiprin 5767:Fenamates 5752:Rofecoxib 5747:Parecoxib 5731:+tramadol 5724:Celecoxib 5706:Zomepirac 5691:Ketorolac 5663:Bromfenac 5642:Tenoxicam 5637:Piroxicam 5632:Meloxicam 5591:Oxaprozin 5547:Ibuprofen 5490:+tramadol 5445:Butacetin 5310:Methadone 5223:Synthetic 5194:+naloxone 5175:Oxycodone 5104:Etorphine 5065:+naloxone 5032:Paregoric 4902:Yohimbine 4877:Tandamine 4847:PRC200-SS 4742:Indanorex 4712:Gamfexine 4702:Fenisorex 4627:Bemegride 4551:5-MeO-αMT 4546:5-MeO-αET 4493:Tropoxane 4267:Picilorex 4257:Naphyrone 4104:Pipradrol 3966:GBR-13119 3961:GBR-13098 3956:GBR-13069 3951:GBR-12935 3946:GBR-12783 3685:Phenatine 3508:Mefenorex 3442:-Deprenyl 3414:Ibopamine 3399:Hordenine 3384:Gepefrine 3335:Fencamine 3290:Ephedrine 3280:Droxidopa 3231:-Deprenyl 3109:Acridorex 2903:Modafinil 2898:Fluorenol 2878:Adrafinil 2870:Eugeroics 2835:Flurothyl 2762:SIB-1553A 2682:Arecoline 2677:Anabasine 2667:AR-R17779 2652:A-366,833 2624:Pentylone 2604:Mexedrone 2599:Methylone 2569:Hexedrone 2544:Cathinone 2534:Bupropion 2461:SKF-82958 2456:SKF-81297 2451:SKF-77434 2355:Sunifiram 2340:Org 26576 2335:Nooglutyl 2287:Ampakines 2267:Octodrine 2204:SCH-58261 2184:CGS-15943 2136:Memantine 2029:: 28–43. 1832:: 27–33. 1468:Chirality 1350:Dowd MJ. 704:rodents. 687:paralytic 628:analgesic 537:E J Corey 516:Synthesis 495:on a leaf 454:nicotinic 438:from the 426:Ecuadoran 9210:Schradan 9185:Fipronil 9137:Muscimol 9079:Rotenone 8910:Birtoxin 8905:Bestoxin 8830:See also 8772:lecithin 8748:prodrugs 8698:Tramadol 8548:ME-18-MC 8513:Ketamine 8503:Ibogaine 8323:BW284C51 8078:RJR-2429 8068:Pyrantel 8028:Nicotine 8023:Morantel 8013:Lobeline 7978:EVP-6124 7973:EVP-4473 7928:Cytisine 7923:Cotinine 7828:A-84,543 7799:Agonists 7732:Category 7495:Onchidal 7475:Mollusca 7386:Bestoxin 7381:Birtoxin 7346:Slotoxin 7336:Agitoxin 7311:Scorpion 7267:Tomatine 7217:Solanine 7162:Mimosine 7137:Gossypol 7122:Divicine 7087:Antiarin 7082:Anisatin 7013:Muscimol 6965:Citrinin 6938:Amatoxin 6884:Cry34Ab1 6812:AB toxin 6806:type III 6718:negative 6476:positive 6465:Exotoxin 6296:Ketamine 6175:Funapide 6170:DSP-2230 6030:Nabilone 6025:Cannabis 5929:Ampyrone 5701:Tolmetin 5696:Sulindac 5673:Etodolac 5651:Acetates 5622:Isoxicam 5596:Suprofen 5586:Naproxen 5460:+codeine 5395:Tramadol 5390:Tilidine 5370:Propiram 5285:Fentanyl 5265:Dezocine 5214:Thebacon 5186:+aspirin 5129:+aspirin 5027:Laudanum 5012:Morphine 5000:+aspirin 4913:ATC code 4777:Mazindol 4737:Idazoxan 4697:Etamivan 4692:Efaroxan 4521:4-HO-αMT 4315:Tropanes 4287:Racetams 4142:4-Cl-PVP 4119:SCH-5472 4079:JZ-IV-10 3971:JJC8-088 3921:2C-B-BZP 3868:Morforex 3863:Morazone 3810:Tyrosine 3805:Tyramine 3795:Tiflorex 3680:Pentorex 3582:Morforex 3528:Mesocarb 3369:Fludorex 3270:Dopamine 3264:Levodopa 3213:Cloforex 2994:2-OH-PEA 2951:Pemoline 2926:Aminorex 2840:Gabazine 2727:Nicotine 2697:Cytisine 2692:Cotinine 2647:A-84,543 2559:Ethylone 2539:Butylone 2484:3,4-DMMC 2446:6-Br-APB 2403:Ketamine 2360:Unifiram 2179:Caffeine 2053:23603417 2004:25690407 1996:19874251 1961:46489298 1918:11093658 1856:23541883 1848:11261802 1758:12783266 1734:: 1–46. 1595:11674810 1560:20932609 1524:22222032 1488:22566097 1452:18644719 1178:98696766 1112:10821107 1040:10821107 916:20337496 822:See also 810:Antidote 800:morphine 773:morphine 758:In vitro 708:Symptoms 676:efficacy 672:Affinity 668:nicotine 660:dopamine 595:nicotine 591:pyridine 526:racemate 503:gaining 441:Ameerega 422:alkaloid 408:(verify) 164:10399316 135:DrugBank 9328:EA-2192 9303:EA-4056 9298:EA-3990 9238:EA-3148 9215:Dimefox 9205:Mipafox 9099:Thujone 8768:Choline 8328:BW-A444 8306:(e.g., 8299:BNC-210 8287:(e.g., 8250:ABT-126 8234:(e.g., 8193:XY-4083 8158:TC-6683 8153:TC-5619 8148:TC-5214 8143:TC-2216 8138:TC-1827 8133:TC-1734 8128:TC-1698 8038:NS-1738 8032:tobacco 7918:Choline 7863:ABT-894 7858:ABT-560 7853:ABT-418 7848:ABT-202 7650:Reptile 7112:Daphnin 7107:Coniine 7092:Brucine 7053:Zeranol 7028:Patulin 6875:toxins 6865:Cry3Bb1 6845:Lipid A 6792:type II 6733:E. coli 6485:Bacilli 6301:Menthol 6276:Camphor 6153:(e.g., 6146:Nefopam 6131:cocaine 6129:(e.g., 5878:Salicin 5615:Oxicams 5440:Bucetin 5412:Viminol 5150:Metopon 4995:Codeine 4983:Opiates 4974:Opioids 4892:Trazium 4817:Nefopam 4772:LR-5182 4473:RTI-386 4468:RTI-371 4463:RTI-354 4458:RTI-336 4453:RTI-229 4448:RTI-177 4443:RTI-150 4438:RTI-126 4428:RTI-120 4423:RTI-113 4418:RTI-112 4358:Cocaine 4147:5-DBFPV 4094:Nocaine 3941:DBL-583 3300:Epinine 3183:Cathine 3059:AL-1095 3004:2,3-MDA 2860:Thujone 2782:TC-2216 2777:TC-1827 2772:TC-1698 2662:ABT-418 2657:ABT-202 2350:S-18986 2320:IDRA-21 2044:3690754 1953:7895043 1807:8183234 1713:9525877 1672:9771274 1631:8071862 1228:9771274 1143:9580626 907:2866194 804:rodents 793:paresis 680:potency 652:central 575:ABT-418 571:ABT-594 468:History 344:Density 279:Formula 144:DB07720 110:PubChem 9308:T-1123 8358:Curare 8275:AQW051 8222:18-MAC 8178:UB-165 7988:GTS-21 7818:5-HIAA 7786:nAChRs 7522:toxins 7417:Spider 7391:BmKAEP 7361:HgeTx1 7302:toxins 7177:Persin 7070:toxins 6898:factor 6879:Cry6Aa 6871:Other 6860:Cry1Ac 6778:type I 6581:Other: 6506:tetani 6456:toxins 6407:Toxins 6340:WHO-EM 6254:Others 5966:Others 5952:  5901:  5727:  5681:  5571:  5558:  5550:  5517:NSAIDs 5398:  5178:  5117:  5089:  5061:  4897:UH-232 4832:O-2172 4585:Others 4413:RTI-51 4408:RTI-32 4403:RTI-31 4177:α-PHPP 4167:α-PHiP 4162:α-PCYP 3926:3C-PEP 3488:MDMPEA 2792:UB-165 2717:GTS-21 2509:4-MEAP 2315:CX-717 2310:CX-691 2305:CX-614 2300:CX-546 2295:CX-516 2051:  2041:  2002:  1994:  1959:  1951:  1916:  1854:  1846:  1805:  1756:  1746:  1711:  1670:  1629:  1593:  1558:  1522:  1486:  1450:  1226:  1176:  1141:  1110:  1038:  914:  904:  730:dioxin 483:opioid 481:of an 357:SMILES 314:208.69 235:ChEMBL 204:C11690 9401:Other 9356:IPTBO 9258:Tabun 9253:Soman 9248:Sarin 9074:Tutin 8746:(and 8728:Xenon 8227:18-MC 8206:(and 7802:(and 7449:PhTx3 7366:HsTx1 7289:Tutin 7282:Ricin 7277:Abrin 7147:Ledol 7068:Plant 6660:delta 6608:Cocci 6569:Botox 5428:-type 5315:NFEPP 5022:Opium 4987:opium 4672:D-161 4592:2-MDP 4503:WF-33 4498:WF-23 4242:MOPPP 4237:MOPVP 4217:MDPBP 4212:MDPPP 4197:DMPVP 4187:α-PVT 4182:α-PVP 4172:α-PHP 4157:α-PBP 4152:α-PPP 3976:MeOPP 3936:CM156 3853:G-130 3572:MMDMA 3503:MDPEA 3054:6-FNE 3049:4-MTA 3044:4-MMA 2494:4-CMC 2489:4-BMC 2000:S2CID 1957:S2CID 1852:S2CID 1174:S2CID 939:(PDF) 644:α4/β2 636:α3/β4 632:α4/β2 548:Corey 428:frog 377:InChI 323:JSmol 215:ChEBI 9423:IDPN 9351:TBPO 9346:TBPS 9026:BMAA 8408:DHβE 8209:NAMs 7805:PAMs 7531:Fish 7439:CSTX 6716:Gram 6656:beta 6474:Gram 4965:N02B 4961:N02A 4917:N06B 4252:MDPV 4232:MPPP 4227:MPHP 4222:MPBP 4207:FPVP 4202:FPOP 3986:oMPP 3981:MBZP 3740:PPAP 3735:PMMA 3730:PMEA 3670:PCMA 3577:MMMA 3567:MMDA 3498:MDPR 3493:MDOH 3478:MDEA 3473:MDBU 3463:MBDB 3394:HMMA 3285:EBDB 3256:DOPA 3173:BPAP 3039:4-MA 2830:DMCM 2345:PEPA 2049:PMID 1992:PMID 1949:PMID 1914:PMID 1844:PMID 1803:PMID 1754:PMID 1744:ISBN 1709:PMID 1668:PMID 1627:PMID 1591:PMID 1556:PMID 1520:PMID 1484:PMID 1448:PMID 1224:PMID 1139:PMID 1108:PMID 1036:PMID 912:PMID 685:The 662:and 654:and 603:base 505:IUCN 456:and 434:and 195:KEGG 175:UNII 124:1204 7406:Pi3 7376:Lq2 6816:AB5 4637:BTQ 4576:αMT 4571:αET 4398:PTT 4393:PIT 4262:PEP 3931:BZP 3725:PMA 3720:PIA 3675:PHA 3665:PCA 3660:PBA 3557:MMA 3163:BOH 3158:BDB 2039:PMC 2031:doi 2027:108 1984:doi 1941:doi 1937:664 1906:doi 1902:896 1879:doi 1834:doi 1830:176 1736:doi 1732:147 1699:doi 1695:273 1658:doi 1623:270 1583:doi 1548:doi 1512:doi 1476:doi 1438:hdl 1430:doi 1330:doi 1303:doi 1254:doi 1214:doi 1166:doi 1135:285 1100:doi 1067:doi 1028:doi 951:doi 902:PMC 894:doi 724:(LD 531:An 114:CID 9445:: 9293:GV 9288:VX 9283:VR 9278:VP 9273:VM 9268:VG 9263:VE 8310:, 8291:, 8242:, 8238:, 6986:, 6952:, 6948:, 6944:, 6353:: 6163:Na 6133:, 5404:, 5196:, 5192:, 5188:, 5184:, 5127:, 5123:, 4963:, 4915:: 3539:, 3351:, 3262:, 3120:, 2047:. 2037:. 2025:. 2021:. 1998:. 1990:. 1980:10 1978:. 1955:. 1947:. 1935:. 1912:. 1900:. 1873:. 1850:. 1842:. 1828:. 1824:. 1799:45 1797:. 1785:^ 1775:. 1752:. 1742:. 1730:. 1707:. 1693:. 1689:. 1666:. 1654:81 1652:. 1648:. 1621:. 1617:. 1603:^ 1589:. 1579:64 1577:. 1554:. 1544:45 1542:. 1518:. 1508:22 1506:. 1482:. 1472:24 1470:. 1446:. 1436:. 1426:18 1424:. 1397:. 1354:. 1342:^ 1326:34 1324:. 1299:34 1297:. 1278:. 1266:^ 1250:34 1248:. 1236:^ 1222:. 1210:81 1208:. 1204:. 1186:^ 1172:. 1162:34 1160:. 1133:. 1129:. 1106:. 1096:17 1094:. 1090:. 1063:45 1061:. 1057:. 1034:. 1024:17 1022:. 1018:. 1004:^ 947:79 945:. 941:. 924:^ 910:. 900:. 890:73 888:. 884:. 795:. 787:, 734:50 726:50 693:. 605:. 577:, 296:Cl 293:13 287:11 76:,4 72:,2 68:(1 8878:e 8871:t 8864:v 8774:) 8770:( 8750:) 8314:) 8295:) 8215:) 8034:) 8030:( 7811:) 7766:e 7759:t 7752:v 7657:: 7652:/ 7559:: 7533:: 7477:: 7419:: 7313:: 6994:) 6982:( 6956:) 6940:( 6814:/ 6742:/ 6658:/ 6654:/ 6555:B 6550:A 6497:: 6397:e 6390:t 6383:v 6165:v 6157:) 6137:) 5958:) 5954:( 5907:) 5903:( 5814:) 5810:( 5733:) 5729:( 5687:) 5683:( 5577:) 5573:( 5564:) 5560:( 5556:) 5552:( 5408:) 5400:( 5291:) 5287:( 5200:) 5180:( 5131:) 5119:( 5095:) 5091:( 5067:) 5063:( 5018:) 5014:( 4985:/ 4967:) 4959:( 4949:e 4942:t 4935:v 4090:) 4086:( 3771:) 3767:( 3628:L 3543:) 3535:( 3440:L 3355:) 3347:( 3266:) 3258:( 3229:D 3124:) 3116:( 2097:e 2090:t 2083:v 2055:. 2033:: 2006:. 1986:: 1963:. 1943:: 1920:. 1908:: 1885:. 1881:: 1875:2 1858:. 1836:: 1809:. 1779:. 1760:. 1738:: 1715:. 1701:: 1674:. 1660:: 1633:. 1597:. 1585:: 1562:. 1550:: 1526:. 1514:: 1490:. 1478:: 1454:. 1440:: 1432:: 1408:. 1383:. 1336:. 1332:: 1309:. 1305:: 1280:4 1260:. 1256:: 1230:. 1216:: 1180:. 1168:: 1145:. 1114:. 1102:: 1075:. 1069:: 1042:. 1030:: 998:. 989:" 985:" 957:. 953:: 918:. 896:: 844:) 325:) 302:2 299:N 290:H 284:C 78:S 74:R 70:R 23:.

Index

Eptifibatide


IUPAC name
CAS Number
140111-52-0
PubChem
1204
DrugBank
DB07720
ChemSpider
10399316
UNII
M6K314F1XX
KEGG
C11690
ChEBI
CHEBI:4803
ChEMBL
ChEMBL298826
ECHA InfoCard
100.162.281
Edit this at Wikidata
Formula
Molar mass
JSmol
Interactive image
Density
SMILES
InChI

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