206:
3540:
279:
31:
321:
InChI=1S/C40H46N4O2/c1-43-15-13-39-31-7-3-5-9-33(31)41-22-30-28-20-36-40(14-16-44(36,2)24-26(28)12-18-46)32-8-4-6-10-34(32)42(38(30)40)21-29(37(39)41)27(19-35(39)43)25(23-43)11-17-45/h3-12,21-22,27-28,35-38,45-46H,13-20,23-24H2,1-2H3/q+2/b25-11-,26-12-,29-21-,30-22-/t27-,28-,35-,36-,37-,38-,39+,40+,43-,44-/m0/s1
461:
After the replacement of curares by these synthetic alternatives, research on toxiferine declined as it was hard to isolate from calabash curare and better alternatives to curares had been found thus decreasing the interest in researching this specific compound. However, curares as a whole have been
833:
and with this a variability in the toxic properties of these analogues. From this it can be concluded that the side groups of toxiferine, mainly those attached to the quaternary ammonium have large effect over its reactivity and affinity, but to this day no research exists that can reliably explain
1021:
is very poor relative to its analogue alcuronium. Toxiferine has a strong receptor affinity, which together with the poor excretion makes it accumulate in the body rapidly after repeated administration. This is another reason why toxiferine has an especially long duration of action in the body.
714:
is thought to be the reason for the binding affinity to the AChRs. The exact reason for the especially high binding affinity of toxiferine to for example muscle-type nAChRs is unknown. There have been attempts at understanding the exact binding of toxiferine in nAChRs, but the models are dated.
807:
A dozen different types of toxiferine were found to exist (designated as toxiferine I to XII), but the different structures of toxiferine II till XII have not been studied in great detail. Toxiferine does have multiple analogues which are researched extensively. Some of these include:
1128:
It has to be said that the duration of paralysis varies a lot between different individual monkeys and doses. It could be as short as 6 minutes but also as long as 85 minutes. In mice the LD100 was determined to be 23 μg/kg with a duration of paralysis around 12 minutes.
799:. Alkaloids are naturally occurring compounds that are basic and contain at least one nitrogen atom. Toxiferine is classified as a dimeric bisindole alkaloid because it is symmetrically constructed from two identical monomeric units, each containing an indole ring.
392:. The paralysis caused by toxiferine is very similar to that caused by tubocurarine, however toxiferine is ~170 times as potent. The preparation of curare poisons involves complex rituals wherein the tribes extract toxins from various plants.
1780:
Zlotos DP, Gündisch D, Ferraro S, Tilotta MC, Stiefl N, Baumann K (December 2004). "Bisquaternary caracurine V and iso-caracurine V salts as ligands for the muscle type of nicotinic acetylcholine receptors: SAR and QSAR studies".
808:
bisnortoxiferine, caracurine V and alcuronium. Caracurine V is, like toxiferine, another naturally occurring curare toxin from the strychnos toxifera. Caracurine V, unlike the other analogues, has a closed ring formed between the
981:. The liver, which is the main site of metabolic activity, can thus not or hardly be reached. When comparing the metabolic activity of toxiferine to that of maybe its most important analogue alcuronium, it is observed that the
558:. By binding to these receptors, toxiferine I prevents acetylcholine from attaching to them. This inhibition blocks the ion channels associated with these receptors from opening, thereby preventing the influx of
411:. They managed to produce only a couple micrograms of this compound as it is quite hard to isolate in large enough quantities to study. This is due to the complexity of curare as it is composed of many different
824:
that gives them their specific affinity for these receptors. The difference in hydroxyl side groups together with most importantly the quaternary ammonium side groups is believed to cause the variability in
730:, increasing the acetylcholine concentrations so it can compete more with the non-depolarizing neuromuscular-blocking drug. By this toxiferine can be freed into the circulation for excretion.
3576:
518:. Which is why it is safe to eat the animal after it has been shot with an arrow covered in toxiferine. It is also believed that because of its activity as muscle paralyzer, it can retain
1939:
Stöckigt J, Panjikar S (December 2007). "Structural biology in plant natural product biosynthesis--architecture of enzymes from monoterpenoid indole and tropane alkaloid biosynthesis".
977:. This may be due to its low lipophilicity. Bis-quaternary nitrogen compounds like toxiferine have shown to be dependent on their lipophilicity to be transported to sites in the
494:. It is hard to extract in large quantities. It is very toxic however, so small quantities will suffice in paralyzing or killing animals while hunting. It could be used as an
1457:"Semisynthetic analogues of toxiferine I and their pharmacological properties at α7 nAChRs, muscle-type nAChRs, and the allosteric binding site of muscarinic M2 receptors"
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which doesn't make it suitable for such procedures. It is also unstable in solution, which further prevents its use in medical settings. Synthetic alternatives like
3779:
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of in this case mainly muscle-type nAChRs. Toxiferine though binds 17 times stronger to muscle-type nAChRs than its pharmacological analogue alcuronium. The
3562:
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3904:
921:
and is not known to be dangerous even though it has a very high potency. Intravenous absorption is thus the only way of effective administration.
812:
and the middle ring. Though the main difference between the analogues are the side groups attached to the positive nitrogen atom, also called the
415:. In 1949 King was able to isolate 12 different types of toxiferines (I to XII). In 1951 some of these toxiferine types were analyzed for their
4081:
1606:
Stovner J, Theodorsen L, Bjelke E (April 1972). "Sensitivity to dimethyltubocurarine and toxiferine with special reference to serum proteins".
2014:"The anticancer agent ellipticine binds to glycosaminoglycans at mildly acidic pH characteristic of the extracellular matrix of tumor tissues"
3859:
4519:
3829:
2051:
Meijer DK, Weitering JG (May 1970). "Curare-like agents: relation between lipid solubility and transport into bile in perfused rat liver".
293:
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3784:
933:. Toxiferine distributes through the body in a way that is similar to other non-depolarizing curare alkaloids. Toxiferine is a highly
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3674:
3669:
3132:
4086:
4359:
1382:
Philippe G, Angenot L, Tits M, Frédérich M (September 2004). "About the toxicity of some
Strychnos species and their alkaloids".
388:. Curare poisons contain many different toxins with similar properties of toxiferine. The most well known component of curare is
1843:"Risks for human health related to the presence of pyrrolizidine alkaloids in honey, tea, herbal infusions and food supplements"
4686:
2215:
2146:
Rosato RR, Stephen EL, Pannier WL (January 1976). "Dose-response data for toxiferine dichloride in monkeys and guinea pigs".
2095:
1434:
842:
Toxiferine is an indole alkaloid. Indole alkaloids are the largest among the alkaloids. They are primarily synthesized using
1703:"Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)"
627:
1571:
Smythies JR (September 1980). "An hypothesis concerning the molecular structure of the nicotinic acetylcholine receptor".
1050:(IM) injections of different doses of toxiferine. The data on rhesus monkeys likely resembles human effects more closely.
2342:
479:
917:
while applied to a sharp tip for killing purposes. When orally ingested, toxiferine is only absorbed minimally into the
726:
is known to be effective at reversing the competitive inhibition of toxiferine and its analogues. Neostigmine works by
3596:
2471:
2463:
2111:
Frey R, Seeger R (March 1961). "Experimental and clinical experience with toxiferine (alkaloid of calabash curare)".
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where it binds to specific receptors. It was also found that toxiferine is distributed to tissues with a high acidic
313:
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can and are still used in anesthetics due to their relatively shorter duration of action and fewer side effects.
63:
1148:"The Science of Useful Plants in the Central Andes Area in South America IX: The Herbs in the Alkaloid Region 1"
4681:
4019:
3615:
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Saxton JE, Gorman AA, Hesse M, Schmid H, Waser PG, Hopff WH (1971). "Bisindole alkaloids". In Saxton JE (ed.).
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properties, allowing them to paralyze animals during hunting, but also possibly kill due to paralysis of the
1147:
301:
123(CC2(C)C/C4=C/CO)5()N(C6=C3C=CC=C6)/C=C7(8(CC9(C)C/%10)9()C\7()C%10=C/CO)()N(C%11=C8C=CC=C%11)/C=C5/4()C1
4645:
145:
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is very similar to the dimeric subunits of toxiferine, though this lacks the quaternary ammonium ion. The
3709:
359:
185:
174:
1841:
Knutsen HK, Alexander J, Barregård L, Bignami M, Brüschweiler B, Ceccatelli S, et al. (July 2017).
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of the ribs. Alkaloids are known to have affinity for such polysaccharides at acidic extracellular pH.
859:
813:
707:
614:
1702:
1536:
Smythies JR (May 1971). "The molecular nature of the acetylcholine receptor: a stereochemical study".
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350:
2013:
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Toxiferine is especially useful as an arrow poison because of its very minimal absorption through
3749:
2555:
2543:
2347:
2336:
1047:
942:
1977:
Waser PG, Reller J (June 1972). "Distribution and pharmacokinetics of 14 C-toxiferine in rats".
403:
was discovered in 1595, however toxiferine was only first isolated and characterized in 1941 by
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946:
886:
817:
703:
582:
555:
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367:
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862:. The exact biosynthetic and possible artificial ways to synthesise toxiferine are not known.
4701:
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404:
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in medical procedures, but were replaced in the 1960s by synthetic curare-like drugs like
8:
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1181:. Specialist Periodical Reports. Cambridge, England: Royal Society of Chemistry. p.
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Hong B, Grzech D, Caputi L, Sonawane P, López CE, Kamileen MO, et al. (July 2022).
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820:. It is this quaternary ammonium ion that both toxiferine and its analogues share with
567:
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3526:
note: some toxins are produced by lower species and pass through intermediate species
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Wieland H, Bähr I, Witkop B (1941). "About the alkaloides from calebash-curare IV".
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Affinities of toxiferine and related compounds for acetylcholine receptor subtypes
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1292:"684. Curare alkaloids. Part X. Some alkaloids of Strychnos toxifera Rob. Schomb"
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into the muscle cell. The prevention of sodium influx leads to an inhibition of
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and may be a related product of its biosynthesis. Especially the intermediate
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Pollard BJ (June 2005). "Neuromuscular blocking agents and reversal agents".
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properties. These types were found to differ slightly in structure and their
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1960:
1925:
1802:
1740:
Plemenkov VV (2001). "Introduction to the
Chemistry of Natural Compounds".
1619:
1517:
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Zlotos DP, Tränkle C, Holzgrabe U, Gündisch D, Jensen AA (September 2014).
1411:
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2508:
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1303:
982:
882:
763:. The parent structure, without counter ions, has the molecular formula C
723:
375:
4589:
4569:
4529:
4469:
4459:
4404:
4394:
4389:
4379:
4354:
4319:
4274:
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4234:
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4159:
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3714:
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3435:
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3330:
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3142:
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3043:
3038:
3023:
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2834:
2829:
2819:
2786:
2476:
2436:
2253:
2248:
2124:
2029:
1990:
1035:
1030:
The effects of toxiferine have been studied in multiple organisms like
878:
847:
843:
830:
748:
666:
530:. This makes the meat more tender for longer and maintains its flavor.
495:
435:
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255:
125:
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2744:
2736:
2643:
2627:
2238:
1952:
962:
100:
909:
Toxiferine is known to enter the body in two different ways: either
374:. The paralysis caused by toxiferine can in turn be antagonized by
4583:
4509:
4324:
4314:
4134:
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3834:
3824:
3789:
3739:
3734:
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3028:
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2623:
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519:
412:
382:
339:
278:
71:(2E)-2-octatriaconta-2,4,6,9,18,20,22,25-octaen-28-ylidene]ethanol
4579:
4559:
4139:
4110:
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3843:
3729:
3664:
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3461:
2923:
2918:
2903:
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2656:
2296:
756:
1840:
1001:
of toxiferine significantly longer when compared to alcuronium.
4169:
3989:
3799:
3584:
3228:
3202:
3172:
2988:
2690:
2671:
2419:
1018:
475:
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165:
1454:
570:. Without depolarization, the muscle fiber cannot generate an
4539:
3177:
3093:
3088:
2958:
2879:
2218:
1061:
1010:
978:
846:. The dimeric subunits of toxiferine bear high similarity to
566:
of the post-synaptic membrane, which is a necessary step for
269:
30:
1779:
1381:
190:
3342:
3250:
1067:
898:
342:
known. It is derived from several plant species, including
3597:
3187:
1881:
1605:
1176:
779:, while the dichloride salt has the molecular formula C
4020:
3616:
929:
The distribution of toxiferine has been researched in
877:. Strictosidine in turn is derived from the alkaloid
816:. The main target of toxiferine and its analogues are
454:. These drugs were safer to use as they had a shorter
694:
Similar to alcuronium, toxiferine is classified as a
2145:
1427:
1179:
The
Alkaloids: v. 1: A Review of Chemical Literature
470:
Toxiferine is most commonly known for its use as an
1700:
498:in medical procedures, however it has a very long
2090:. Medicinal chemistry. New York: Academic press.
1259:
937:substance and because of this also generally not
4668:
1938:
1217:British Journal of Pharmacology and Chemotherapy
113:
2050:
1512:, Treasure Island (FL): StatPearls Publishing,
1377:
1375:
1054:The toxicity of toxiferine I in rhesus monkeys
358:by indigenous peoples in South America for its
88:
4515:Trimetaphan camsilate (trimethaphan camsylate)
1701:Moss GP, Smith P, Tavernier D (January 1995).
1429:. London: Palgrave Macmillan. pp. 65–96.
381:Toxiferine is the most important component in
4656:Acetylcholine metabolism/transport modulators
3570:
2201:
1972:
1970:
1932:
1450:
1448:
1446:
1325:
1323:
1321:
1152:Foods & Food Ingredients Journal of Japan
865:It is believed though that toxiferine may be
710:that toxiferine and its analogues share with
526:from releasing after death and by this delay
4651:Muscarinic acetylcholine receptor modulators
2284:
1372:
1206:
1204:
1202:
696:non-depolarizing neuromuscular-blocking drug
1976:
1285:
1283:
858:was solved in 2022. It is also possible to
3577:
3563:
2208:
2194:
2110:
1967:
1443:
1318:
1210:
718:
204:
133:
3602:Tooltip Nicotinic acetylcholine receptors
3133:Androctonus australis hector insect toxin
1915:
1866:
1739:
1643:Anaesthesia & Intensive Care Medicine
1480:
1355:
1296:Journal of the Chemical Society (Resumed)
1236:
1199:
1145:
834:the structural reactivity of toxiferine.
153:
4145:Candocuronium iodide (chandonium iodide)
1570:
1535:
1506:"Nondepolarizing Neuromuscular Blockers"
1280:
462:(and still are) extensively researched.
2113:Canadian Anaesthetists' Society Journal
1640:
1503:
354:. Historically, it has been used as an
200:
4669:
4025:Tooltip negative allosteric modulators
3621:Tooltip positive allosteric modulators
2085:
1757:Alkaloids. Nature's Curse or Blessing?
1424:
1329:
941:. Toxiferine does not easily pass the
533:
16:One of the most toxic plant alkaloids.
3558:
2189:
2011:
1754:
1213:"The pharmacology of the toxiferines"
1025:
1009:Toxiferine is mainly excreted in the
173:
1783:Bioorganic & Medicinal Chemistry
1289:
482:. It is extracted from plants, like
2148:Toxicology and Applied Pharmacology
1683:. U.S. National Library of Medicine
973:Toxiferine does not have any known
104:
13:
2487:Staphylococcal Enterotoxin B (SEB)
1859:10.1016/B978-0-12-816455-6.00015-9
1229:10.1111/j.1476-5381.1951.tb00643.x
860:artificially synthesise strychnine
14:
4713:
4230:Dimethyltubocurarine (metocurine)
1262:Justus Liebigs Annalen der Chemie
574:, resulting in muscle paralysis.
548:nicotinic acetylcholine receptors
338:, is one of the most toxic plant
3586:Nicotinic acetylcholine receptor
3539:
3538:
2053:European Journal of Pharmacology
1538:European Journal of Pharmacology
1211:Paton WD, Perry WL (June 1951).
602:nicotinic acetylcholine receptor
239:
233:
29:
4610:Meclofenoxate (centrophenoxine)
3935:Suxethonium (succinyldicholine)
3930:Suxamethonium (succinylcholine)
2571:Extracellular adenylate cyclase
2139:
2104:
2079:
2044:
2005:
1875:
1834:
1809:
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1748:
1733:
1694:
1669:
1634:
1599:
1564:
1529:
1497:
1336:British Journal of Pharmacology
924:
837:
728:inhibiting acetylcholinesterase
698:. These are drugs that inhibit
1608:British Journal of Anaesthesia
1418:
1253:
1170:
1139:
465:
245:
227:
1:
4687:Quaternary ammonium compounds
4646:Receptor/signaling modulators
4300:Hexamethonium (benzohexonium)
2723:Fibronectin binding protein A
1404:10.1016/j.toxicon.2004.05.006
1132:
968:
904:
366:. Toxiferine functions as an
2168:10.1016/0041-008x(76)90115-0
2065:10.1016/0014-2999(70)90284-0
2012:Zsila F (21 December 2015).
1884:"Biosynthesis of strychnine"
1585:10.1016/0306-9877(80)90046-8
1550:10.1016/0014-2999(71)90136-1
1079:Margin of safety (LD1/ED99)
1004:
997:side chains. This makes the
802:
738:
733:
585:, but especially potent for
7:
4380:Methorphan (racemethorphan)
3710:Bephenium hydroxynaphthoate
2464:Staphylococcus aureus alpha
2442:Panton–Valentine leukocidin
1759:. Zürich: VHCA, Wiley-VCH.
1461:Journal of Natural Products
945:. It is mostly retained in
538:Toxiferine I competes with
509:
10:
4718:
3760:Dimethylphenylpiperazinium
2482:Toxic shock syndrome toxin
1908:10.1038/s41586-022-04950-4
1707:Pure and Applied Chemistry
1655:10.1383/anes.6.6.189.65784
1330:Bowman WC (January 2006).
856:biosynthesis of strychnine
689:
615:alpha-7 nicotinic receptor
395:
217:Chemical and physical data
4638:
4552:
4013:
3609:
3595:
3534:
3521:
3459:
3379:(+)-Allopumiliotoxin 267A
3366:
3340:
3329:
3284:
3226:
3120:
3109:
2878:
2735:
2706:
2642:
2579:
2526:
2499:
2452:
2427:
2418:
2391:
2304:
2295:
2275:
2264:
1795:10.1016/j.bmc.2004.08.053
993:than toxiferine with its
626:
613:
600:
577:Toxiferine I is a potent
491:chondrodendron tomentosum
351:Chondrodendron tomentosum
309:
289:
267:
254:
221:
216:
184:
164:
144:
124:
99:
79:
59:
54:
42:
37:
28:
4620:Phosphatidylethanolamine
2772:beta-Nitropropionic acid
1274:10.1002/jlac.19415470111
989:make it more potent for
852:Wieland-Gumlich aldehyde
761:quaternary ammonium salt
708:quaternary ammonium salt
628:muscarinic acetylcholine
4400:Morphanol (racemorphan)
4340:Laudexium (laudolissin)
3750:Desformylflustrabromine
2556:Heat-labile enterotoxin
2547:heat-stable enterotoxin
1941:Natural Product Reports
1719:10.1351/pac199567081307
1504:Clar DT, Liu M (2024),
1164:10.34457/ffij.228.4_336
892:
818:acetylcholine receptors
814:quaternary ammonium ion
719:Reversing the mechanism
583:acetylcholine receptors
458:and less side effects.
4692:Neuromuscular blockers
2665:Bacillus thuringiensis
1348:10.1038/sj.bjp.0706404
1342:(Suppl 1): S277–S286.
1082:Time till onset (min)
887:strictosidine synthase
885:through the action of
704:competitive inhibition
556:neuromuscular junction
368:acetylcholine receptor
360:neuromuscular blocking
4682:Nicotinic antagonists
4605:Glycerophosphocholine
1332:"Neuromuscular block"
1017:of toxiferine by the
546:, for binding to the
480:south american tribes
4600:Dimethylethanolamine
4465:Rapacuronium bromide
4445:Pipecuronium bromide
4285:Gantacurium chloride
4245:Dizocilpine (MK-801)
3830:MEM-63,908 (RG-3487)
3780:Ethoxysebacylcholine
2566:Pseudomonas exotoxin
1620:10.1093/bja/44.4.374
1304:10.1039/jr9490003263
1146:Mitsunaga T (2023).
959:intervertebral discs
755:structure with each
4615:Phosphatidylcholine
4500:Threohydrobupropion
4485:Stercuronium iodide
4420:Pancuronium bromide
2160:1976ToxAP..35..107R
1900:2022Natur.607..617H
1396:2004Txcn...44..405P
1055:
943:blood-brain barrier
897:This describes the
743:Toxiferine I is an
700:signal transduction
605:(muscle-type nAChR)
594:
534:Mechanism of action
434:were later used as
364:respiratory muscles
25:
4535:Vecuronium bromide
4475:Rocuronium bromide
4385:Methyllycaconitine
4310:Hydroxynorketamine
4205:Dextropropoxyphene
4190:Dehydronorketamine
4180:Dacuronium bromide
3482:Alpha-Bungarotoxin
2652:Lipopolysaccharide
2610:Pore-forming toxin
2125:10.1007/BF03021339
2086:Ariëns EJ (1971).
2030:10.1039/C5RA23437A
1991:10.1007/BF01965855
1979:Agents and Actions
1713:(8–9): 1307–1375.
1573:Medical Hypotheses
1425:Bowman WC (1986).
1053:
1026:Toxicological data
999:duration of action
975:metabolic pathways
955:mucopolysaccharide
831:metabolic activity
592:
568:muscle contraction
500:duration of action
485:strychnos toxifera
456:duration of action
345:Strychnos toxifera
90:6888-23-9;302-30-7
21:
4664:
4663:
4625:Phosphorylcholine
4563:
4548:
4547:
4345:Levacetylmethadol
4225:Dihydrochandonium
4105:sodium thiopental
3775:Ethanol (alcohol)
3552:
3551:
3517:
3516:
3487:Beta-Bungarotoxin
3431:Pumiliotoxin 251D
3325:
3324:
2731:
2730:
2718:Clumping factor A
2638:
2637:
2522:
2521:
2495:
2494:
2414:
2413:
2097:978-0-12-060301-5
1894:(7919): 617–622.
1789:(23): 6277–6285.
1473:10.1021/np500259j
1436:978-1-349-08028-1
1126:
1125:
1074:Therapeutic index
991:biotransformation
869:derived from the
827:receptor affinity
687:
686:
635:(allosteric site)
587:muscle-type nAChR
329:
328:
280:Interactive image
186:CompTox Dashboard
4709:
4677:Indole alkaloids
4557:
4495:Thiocolchicoside
4305:Hydroxybupropion
4200:Dextromethorphan
4072:Allopregnanolone
4026:
4022:
3925:Suberyldicholine
3635:6-Chloronicotine
3622:
3618:
3607:
3606:
3603:
3599:
3579:
3572:
3565:
3556:
3555:
3542:
3541:
3470:
3426:Histrionicotoxin
3372:
3346:
3338:
3337:
3290:
3244:Alpha-latrotoxin
3232:
3126:
3118:
3117:
2850:Sterigmatocystin
2802:, Fumonisin B3,
2766:epsilon-amanitin
2685:B. thuringiensis
2514:Diphtheria toxin
2457:
2425:
2424:
2394:
2310:
2302:
2301:
2293:
2292:
2282:
2281:
2273:
2272:
2210:
2203:
2196:
2187:
2186:
2180:
2179:
2143:
2137:
2136:
2108:
2102:
2101:
2083:
2077:
2076:
2048:
2042:
2041:
2009:
2003:
2002:
1974:
1965:
1964:
1953:10.1039/b711935f
1936:
1930:
1929:
1919:
1879:
1873:
1872:
1870:
1838:
1832:
1831:
1829:
1828:
1821:roempp.thieme.de
1813:
1807:
1806:
1777:
1771:
1770:
1755:Hesse M (2002).
1752:
1746:
1745:
1737:
1731:
1730:
1698:
1692:
1691:
1689:
1688:
1673:
1667:
1666:
1638:
1632:
1631:
1603:
1597:
1596:
1568:
1562:
1561:
1533:
1527:
1526:
1525:
1524:
1501:
1495:
1494:
1484:
1467:(9): 2006–2013.
1452:
1441:
1440:
1422:
1416:
1415:
1379:
1370:
1369:
1359:
1327:
1316:
1315:
1287:
1278:
1277:
1257:
1251:
1250:
1240:
1208:
1197:
1196:
1174:
1168:
1167:
1143:
1056:
1052:
913:by ingestion or
881:and the terpene
873:indole alkaloid
867:biosynthetically
595:
591:
572:action potential
554:membrane of the
544:neurotransmitter
474:alongside other
334:, also known as
282:
262:
247:
241:
235:
229:
209:
208:
194:
192:
177:
157:
137:
117:
107:
106:
92:
33:
26:
24:
20:
4717:
4716:
4712:
4711:
4710:
4708:
4707:
4706:
4667:
4666:
4665:
4660:
4634:
4556:
4544:
4150:Chlorisondamine
4024:
4017:
4009:
3620:
3613:
3601:
3591:
3583:
3553:
3548:
3530:
3513:
3509:Cardiotoxin III
3465:
3460:
3455:
3367:
3362:
3341:
3333:
3321:
3285:
3280:
3227:
3222:
3121:
3113:
3105:
3009:Resiniferatoxin
2874:
2727:
2709:
2702:
2667:delta endotoxin
2634:
2575:
2561:Pertussis toxin
2529:
2518:
2491:
2453:
2448:
2410:
2406:Listeriolysin O
2392:
2387:
2305:
2287:
2267:
2260:
2214:
2184:
2183:
2144:
2140:
2109:
2105:
2098:
2084:
2080:
2049:
2045:
2010:
2006:
1975:
1968:
1947:(6): 1382–400.
1937:
1933:
1880:
1876:
1839:
1835:
1826:
1824:
1817:"C-Toxiferin I"
1815:
1814:
1810:
1778:
1774:
1767:
1753:
1749:
1738:
1734:
1699:
1695:
1686:
1684:
1675:
1674:
1670:
1639:
1635:
1604:
1600:
1569:
1565:
1534:
1530:
1522:
1520:
1502:
1498:
1453:
1444:
1437:
1423:
1419:
1380:
1373:
1328:
1319:
1290:King H (1949).
1288:
1281:
1258:
1254:
1209:
1200:
1193:
1175:
1171:
1144:
1140:
1135:
1028:
1007:
985:side chains of
971:
947:motor endplates
927:
907:
901:of toxiferine.
895:
840:
810:hydroxyl groups
805:
798:
794:
790:
786:
782:
778:
774:
770:
766:
745:indole alkaloid
741:
736:
721:
692:
640:
636:
633:
629:
623:
619:
617:
610:
606:
604:
536:
512:
468:
421:pharmacological
398:
325:
322:
317:
316:
305:
302:
297:
296:
285:
260:
250:
244:
238:
232:
212:
188:
180:
160:
140:
120:
103:
95:
75:
72:
67:
66:
46:C-Toxiferine I
17:
12:
11:
5:
4715:
4705:
4704:
4699:
4694:
4689:
4684:
4679:
4662:
4661:
4659:
4658:
4653:
4648:
4643:
4639:
4636:
4635:
4633:
4632:
4627:
4622:
4617:
4612:
4607:
4602:
4597:
4592:
4587:
4577:
4572:
4566:
4564:
4550:
4549:
4546:
4545:
4543:
4542:
4537:
4532:
4527:
4522:
4517:
4512:
4507:
4502:
4497:
4492:
4487:
4482:
4477:
4472:
4467:
4462:
4457:
4452:
4447:
4442:
4437:
4432:
4427:
4422:
4417:
4412:
4407:
4402:
4397:
4392:
4387:
4382:
4377:
4372:
4367:
4362:
4357:
4352:
4347:
4342:
4337:
4332:
4330:Kynurenic acid
4327:
4322:
4317:
4312:
4307:
4302:
4297:
4292:
4287:
4282:
4277:
4272:
4267:
4262:
4257:
4252:
4247:
4242:
4237:
4232:
4227:
4222:
4217:
4212:
4207:
4202:
4197:
4192:
4187:
4182:
4177:
4172:
4167:
4162:
4157:
4152:
4147:
4142:
4137:
4132:
4127:
4124:κ-bungarotoxin
4120:α-bungarotoxin
4113:
4108:
4094:
4089:
4084:
4079:
4074:
4069:
4064:
4059:
4058:, many others)
4048:α-bungarotoxin
4041:
4036:
4030:
4028:
4011:
4010:
4008:
4007:
4002:
3997:
3992:
3987:
3982:
3980:Tribendimidine
3977:
3972:
3967:
3962:
3957:
3952:
3947:
3942:
3937:
3932:
3927:
3922:
3917:
3912:
3907:
3905:Sebacylcholine
3902:
3897:
3892:
3887:
3882:
3877:
3872:
3867:
3862:
3857:
3852:
3847:
3837:
3832:
3827:
3822:
3817:
3812:
3807:
3802:
3797:
3792:
3787:
3782:
3777:
3772:
3767:
3762:
3757:
3752:
3747:
3742:
3737:
3732:
3727:
3722:
3720:Butyrylcholine
3717:
3712:
3707:
3702:
3697:
3692:
3687:
3682:
3677:
3672:
3667:
3662:
3657:
3652:
3647:
3642:
3637:
3632:
3626:
3624:
3604:
3593:
3592:
3582:
3581:
3574:
3567:
3559:
3550:
3549:
3547:
3546:
3535:
3532:
3531:
3529:
3528:
3522:
3519:
3518:
3515:
3514:
3512:
3511:
3506:
3501:
3496:
3491:
3490:
3489:
3484:
3473:
3471:
3457:
3456:
3454:
3453:
3451:Zetekitoxin AB
3448:
3443:
3438:
3433:
3428:
3423:
3418:
3417:
3416:
3411:
3406:
3401:
3396:
3386:
3381:
3375:
3373:
3364:
3363:
3361:
3360:
3355:
3349:
3347:
3335:
3327:
3326:
3323:
3322:
3320:
3319:
3314:
3309:
3304:
3299:
3293:
3291:
3282:
3281:
3279:
3278:
3273:
3268:
3263:
3258:
3253:
3248:
3247:
3246:
3235:
3233:
3224:
3223:
3221:
3220:
3215:
3210:
3205:
3200:
3195:
3190:
3185:
3180:
3175:
3170:
3165:
3160:
3155:
3150:
3145:
3140:
3135:
3129:
3127:
3115:
3107:
3106:
3104:
3103:
3098:
3097:
3096:
3091:
3081:
3076:
3071:
3066:
3061:
3056:
3051:
3046:
3041:
3036:
3031:
3026:
3021:
3016:
3011:
3006:
3001:
2999:Pseudaconitine
2996:
2991:
2986:
2981:
2976:
2971:
2966:
2961:
2956:
2951:
2946:
2941:
2939:Djenkolic acid
2936:
2931:
2926:
2921:
2916:
2911:
2906:
2901:
2896:
2891:
2885:
2883:
2876:
2875:
2873:
2872:
2867:
2862:
2857:
2852:
2847:
2842:
2837:
2832:
2827:
2822:
2817:
2812:
2807:
2789:
2784:
2779:
2774:
2769:
2762:gamma-amanitin
2754:alpha-amanitin
2747:
2741:
2739:
2733:
2732:
2729:
2728:
2726:
2725:
2720:
2714:
2712:
2704:
2703:
2701:
2700:
2699:
2698:
2693:
2681:
2680:
2679:
2674:
2661:
2660:
2659:
2648:
2646:
2640:
2639:
2636:
2635:
2633:
2632:
2631:
2630:
2614:
2613:
2612:
2600:
2599:
2598:
2585:
2583:
2577:
2576:
2574:
2573:
2568:
2563:
2558:
2549:
2541:
2534:
2532:
2524:
2523:
2520:
2519:
2517:
2516:
2511:
2505:
2503:
2501:Actinomycetota
2497:
2496:
2493:
2492:
2490:
2489:
2484:
2479:
2474:
2460:
2458:
2455:Staphylococcus
2450:
2449:
2447:
2446:
2445:
2444:
2434:
2428:
2422:
2416:
2415:
2412:
2411:
2409:
2408:
2403:
2397:
2395:
2389:
2388:
2386:
2385:
2384:
2383:
2371:
2370:
2369:
2364:
2352:
2351:
2350:
2345:
2333:
2332:
2331:
2326:
2313:
2311:
2299:
2290:
2279:
2270:
2262:
2261:
2259:
2258:
2257:
2256:
2251:
2246:
2241:
2236:
2231:
2226:
2213:
2212:
2205:
2198:
2190:
2182:
2181:
2154:(1): 107–111.
2138:
2103:
2096:
2078:
2059:(2): 283–289.
2043:
2024:(1): 810–814.
2004:
1985:(4): 170–175.
1966:
1931:
1874:
1853:(7): 505–567.
1833:
1808:
1772:
1765:
1747:
1732:
1693:
1668:
1649:(6): 189–192.
1633:
1614:(4): 374–380.
1598:
1579:(9): 943–950.
1563:
1544:(3): 268–279.
1528:
1496:
1442:
1435:
1417:
1390:(4): 405–416.
1371:
1317:
1279:
1252:
1223:(2): 299–310.
1198:
1191:
1169:
1158:(4): 336–350.
1137:
1136:
1134:
1131:
1124:
1123:
1120:
1117:
1114:
1111:
1108:
1104:
1103:
1100:
1097:
1094:
1091:
1088:
1084:
1083:
1080:
1077:
1071:
1065:
1059:
1032:rhesus monkeys
1027:
1024:
1006:
1003:
970:
967:
926:
923:
906:
903:
894:
891:
839:
836:
804:
801:
796:
792:
788:
784:
780:
776:
772:
768:
764:
740:
737:
735:
732:
720:
717:
691:
688:
685:
684:
682:
679:
677:
674:
672:
669:
663:
662:
660:
657:
655:
652:
650:
647:
643:
642:
638:
631:
625:
621:
612:
608:
599:
564:depolarization
535:
532:
516:oral ingestion
511:
508:
467:
464:
397:
394:
336:c-toxiferine I
327:
326:
324:
323:
320:
312:
311:
310:
307:
306:
304:
303:
300:
292:
291:
290:
287:
286:
284:
283:
275:
273:
265:
264:
258:
252:
251:
248:
242:
236:
230:
225:
219:
218:
214:
213:
211:
210:
202:DTXSID30897243
197:
195:
182:
181:
179:
178:
170:
168:
162:
161:
159:
158:
150:
148:
142:
141:
139:
138:
130:
128:
122:
121:
119:
118:
110:
108:
97:
96:
94:
93:
85:
83:
77:
76:
74:
73:
70:
62:
61:
60:
57:
56:
52:
51:
48:C-Toxiferin I
44:
40:
39:
35:
34:
15:
9:
6:
4:
3:
2:
4714:
4703:
4700:
4698:
4695:
4693:
4690:
4688:
4685:
4683:
4680:
4678:
4675:
4674:
4672:
4657:
4654:
4652:
4649:
4647:
4644:
4641:
4640:
4637:
4631:
4628:
4626:
4623:
4621:
4618:
4616:
4613:
4611:
4608:
4606:
4603:
4601:
4598:
4596:
4593:
4591:
4588:
4585:
4581:
4578:
4576:
4573:
4571:
4568:
4567:
4565:
4561:
4555:
4551:
4541:
4538:
4536:
4533:
4531:
4528:
4526:
4523:
4521:
4518:
4516:
4513:
4511:
4508:
4506:
4503:
4501:
4498:
4496:
4493:
4491:
4488:
4486:
4483:
4481:
4478:
4476:
4473:
4471:
4468:
4466:
4463:
4461:
4458:
4456:
4453:
4451:
4448:
4446:
4443:
4441:
4440:Phencyclidine
4438:
4436:
4433:
4431:
4428:
4426:
4423:
4421:
4418:
4416:
4413:
4411:
4410:Nitrous oxide
4408:
4406:
4403:
4401:
4398:
4396:
4393:
4391:
4388:
4386:
4383:
4381:
4378:
4376:
4373:
4371:
4368:
4366:
4363:
4361:
4358:
4356:
4353:
4351:
4350:Levomethadone
4348:
4346:
4343:
4341:
4338:
4336:
4333:
4331:
4328:
4326:
4323:
4321:
4318:
4316:
4313:
4311:
4308:
4306:
4303:
4301:
4298:
4296:
4295:Hexafluronium
4293:
4291:
4288:
4286:
4283:
4281:
4278:
4276:
4273:
4271:
4268:
4266:
4263:
4261:
4258:
4256:
4253:
4251:
4248:
4246:
4243:
4241:
4238:
4236:
4233:
4231:
4228:
4226:
4223:
4221:
4218:
4216:
4213:
4211:
4208:
4206:
4203:
4201:
4198:
4196:
4193:
4191:
4188:
4186:
4185:Decamethonium
4183:
4181:
4178:
4176:
4173:
4171:
4168:
4166:
4163:
4161:
4158:
4156:
4155:Cisatracurium
4153:
4151:
4148:
4146:
4143:
4141:
4138:
4136:
4133:
4131:
4128:
4125:
4121:
4117:
4116:Bungarotoxins
4114:
4112:
4109:
4106:
4102:
4101:pentobarbital
4098:
4095:
4093:
4090:
4088:
4085:
4083:
4080:
4078:
4075:
4073:
4070:
4068:
4065:
4063:
4060:
4057:
4053:
4049:
4045:
4044:α-Neurotoxins
4042:
4040:
4037:
4035:
4032:
4031:
4029:
4023:
4016:
4012:
4006:
4003:
4001:
3998:
3996:
3993:
3991:
3988:
3986:
3983:
3981:
3978:
3976:
3973:
3971:
3968:
3966:
3963:
3961:
3958:
3956:
3953:
3951:
3948:
3946:
3943:
3941:
3938:
3936:
3933:
3931:
3928:
3926:
3923:
3921:
3918:
3916:
3913:
3911:
3908:
3906:
3903:
3901:
3898:
3896:
3893:
3891:
3888:
3886:
3883:
3881:
3878:
3876:
3873:
3871:
3868:
3866:
3863:
3861:
3858:
3856:
3853:
3851:
3848:
3845:
3841:
3838:
3836:
3833:
3831:
3828:
3826:
3823:
3821:
3818:
3816:
3813:
3811:
3808:
3806:
3803:
3801:
3798:
3796:
3793:
3791:
3788:
3786:
3783:
3781:
3778:
3776:
3773:
3771:
3768:
3766:
3763:
3761:
3758:
3756:
3753:
3751:
3748:
3746:
3745:Decamethonium
3743:
3741:
3738:
3736:
3733:
3731:
3728:
3726:
3723:
3721:
3718:
3716:
3713:
3711:
3708:
3706:
3703:
3701:
3698:
3696:
3693:
3691:
3688:
3686:
3683:
3681:
3680:Acetylcholine
3678:
3676:
3673:
3671:
3668:
3666:
3663:
3661:
3658:
3656:
3653:
3651:
3648:
3646:
3643:
3641:
3638:
3636:
3633:
3631:
3628:
3627:
3625:
3619:
3612:
3608:
3605:
3600:
3594:
3590:
3587:
3580:
3575:
3573:
3568:
3566:
3561:
3560:
3557:
3545:
3537:
3536:
3533:
3527:
3524:
3523:
3520:
3510:
3507:
3505:
3502:
3500:
3497:
3495:
3492:
3488:
3485:
3483:
3480:
3479:
3478:
3475:
3474:
3472:
3468:
3463:
3458:
3452:
3449:
3447:
3444:
3442:
3441:Samandaridine
3439:
3437:
3434:
3432:
3429:
3427:
3424:
3422:
3419:
3415:
3414:Marinobufagin
3412:
3410:
3407:
3405:
3402:
3400:
3397:
3395:
3392:
3391:
3390:
3387:
3385:
3384:Batrachotoxin
3382:
3380:
3377:
3376:
3374:
3370:
3365:
3359:
3356:
3354:
3351:
3350:
3348:
3344:
3339:
3336:
3332:
3328:
3318:
3315:
3313:
3310:
3308:
3305:
3303:
3300:
3298:
3295:
3294:
3292:
3288:
3283:
3277:
3274:
3272:
3269:
3267:
3264:
3262:
3259:
3257:
3254:
3252:
3249:
3245:
3242:
3241:
3240:
3237:
3236:
3234:
3230:
3225:
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:
3151:
3149:
3146:
3144:
3141:
3139:
3138:Charybdotoxin
3136:
3134:
3131:
3130:
3128:
3124:
3119:
3116:
3112:
3108:
3102:
3099:
3095:
3092:
3090:
3087:
3086:
3085:
3082:
3080:
3077:
3075:
3072:
3070:
3067:
3065:
3062:
3060:
3057:
3055:
3052:
3050:
3049:Solauricidine
3047:
3045:
3042:
3040:
3037:
3035:
3032:
3030:
3027:
3025:
3022:
3020:
3017:
3015:
3012:
3010:
3007:
3005:
3002:
3000:
2997:
2995:
2994:Protoanemonin
2992:
2990:
2987:
2985:
2982:
2980:
2979:Oenanthotoxin
2977:
2975:
2972:
2970:
2967:
2965:
2962:
2960:
2957:
2955:
2952:
2950:
2947:
2945:
2942:
2940:
2937:
2935:
2932:
2930:
2927:
2925:
2922:
2920:
2917:
2915:
2912:
2910:
2907:
2905:
2902:
2900:
2897:
2895:
2892:
2890:
2887:
2886:
2884:
2881:
2877:
2871:
2868:
2866:
2863:
2861:
2858:
2856:
2855:Trichothecene
2853:
2851:
2848:
2846:
2843:
2841:
2838:
2836:
2833:
2831:
2828:
2826:
2823:
2821:
2818:
2816:
2815:Ibotenic acid
2813:
2811:
2808:
2805:
2801:
2797:
2793:
2790:
2788:
2785:
2783:
2780:
2778:
2775:
2773:
2770:
2767:
2763:
2759:
2758:beta-amanitin
2755:
2751:
2748:
2746:
2743:
2742:
2740:
2738:
2734:
2724:
2721:
2719:
2716:
2715:
2713:
2711:
2705:
2697:
2694:
2692:
2689:
2688:
2686:
2682:
2678:
2675:
2673:
2670:
2669:
2668:
2666:
2662:
2658:
2655:
2654:
2653:
2650:
2649:
2647:
2645:
2641:
2629:
2625:
2622:
2621:
2620:
2619:
2615:
2611:
2608:
2607:
2606:
2605:
2601:
2597:
2594:
2593:
2592:
2591:
2587:
2586:
2584:
2582:
2578:
2572:
2569:
2567:
2564:
2562:
2559:
2557:
2553:
2552:Cholera toxin
2550:
2548:
2546:
2542:
2539:
2536:
2535:
2533:
2531:
2525:
2515:
2512:
2510:
2507:
2506:
2504:
2502:
2498:
2488:
2485:
2483:
2480:
2478:
2475:
2473:
2469:
2465:
2462:
2461:
2459:
2456:
2451:
2443:
2440:
2439:
2438:
2435:
2433:
2430:
2429:
2426:
2423:
2421:
2417:
2407:
2404:
2402:
2401:Anthrax toxin
2399:
2398:
2396:
2390:
2382:
2379:
2378:
2377:
2376:
2372:
2368:
2365:
2363:
2360:
2359:
2358:
2357:
2353:
2349:
2346:
2344:
2341:
2340:
2339:
2338:
2334:
2330:
2327:
2325:
2324:Tetanospasmin
2322:
2321:
2320:
2319:
2315:
2314:
2312:
2308:
2303:
2300:
2298:
2294:
2291:
2289:
2283:
2280:
2278:
2274:
2271:
2269:
2263:
2255:
2252:
2250:
2247:
2245:
2242:
2240:
2237:
2235:
2232:
2230:
2227:
2225:
2222:
2221:
2220:
2217:
2216:
2211:
2206:
2204:
2199:
2197:
2192:
2191:
2188:
2177:
2173:
2169:
2165:
2161:
2157:
2153:
2149:
2142:
2134:
2130:
2126:
2122:
2119:(2): 99–117.
2118:
2114:
2107:
2099:
2093:
2089:
2082:
2074:
2070:
2066:
2062:
2058:
2054:
2047:
2039:
2035:
2031:
2027:
2023:
2019:
2015:
2008:
2000:
1996:
1992:
1988:
1984:
1980:
1973:
1971:
1962:
1958:
1954:
1950:
1946:
1942:
1935:
1927:
1923:
1918:
1913:
1909:
1905:
1901:
1897:
1893:
1889:
1885:
1878:
1869:
1864:
1860:
1856:
1852:
1848:
1844:
1837:
1822:
1818:
1812:
1804:
1800:
1796:
1792:
1788:
1784:
1776:
1768:
1766:3-906390-24-1
1762:
1758:
1751:
1743:
1736:
1728:
1724:
1720:
1716:
1712:
1709:(in German).
1708:
1704:
1697:
1682:
1678:
1672:
1664:
1660:
1656:
1652:
1648:
1644:
1637:
1629:
1625:
1621:
1617:
1613:
1609:
1602:
1594:
1590:
1586:
1582:
1578:
1574:
1567:
1559:
1555:
1551:
1547:
1543:
1539:
1532:
1519:
1515:
1511:
1507:
1500:
1492:
1488:
1483:
1478:
1474:
1470:
1466:
1462:
1458:
1451:
1449:
1447:
1438:
1432:
1428:
1421:
1413:
1409:
1405:
1401:
1397:
1393:
1389:
1385:
1378:
1376:
1367:
1363:
1358:
1353:
1349:
1345:
1341:
1337:
1333:
1326:
1324:
1322:
1313:
1309:
1305:
1301:
1298:: 3263–3271.
1297:
1293:
1286:
1284:
1275:
1271:
1267:
1263:
1256:
1248:
1244:
1239:
1234:
1230:
1226:
1222:
1218:
1214:
1207:
1205:
1203:
1194:
1192:0-85186-257-8
1188:
1184:
1180:
1173:
1165:
1161:
1157:
1153:
1149:
1142:
1138:
1130:
1121:
1118:
1115:
1112:
1109:
1106:
1105:
1101:
1098:
1095:
1092:
1089:
1086:
1085:
1081:
1078:
1075:
1072:
1069:
1066:
1063:
1060:
1058:
1057:
1051:
1049:
1048:intramuscular
1045:
1041:
1037:
1033:
1023:
1020:
1016:
1012:
1002:
1000:
996:
992:
988:
984:
980:
976:
966:
964:
960:
957:content like
956:
952:
951:sciatic nerve
948:
944:
940:
936:
935:water soluble
932:
922:
920:
916:
915:intravenously
912:
902:
900:
890:
888:
884:
880:
876:
875:strictosidine
872:
871:monoterpenoid
868:
863:
861:
857:
853:
849:
845:
835:
832:
828:
823:
822:acetylcholine
819:
815:
811:
800:
762:
759:containing a
758:
754:
750:
747:derived from
746:
731:
729:
725:
716:
713:
712:acetylcholine
709:
705:
701:
697:
683:
680:
678:
675:
673:
670:
668:
665:
664:
661:
658:
656:
653:
651:
648:
645:
644:
634:
616:
603:
597:
596:
590:
588:
584:
580:
575:
573:
569:
565:
561:
557:
553:
552:post-synaptic
549:
545:
541:
540:acetylcholine
531:
529:
525:
521:
517:
507:
505:
501:
497:
493:
492:
487:
486:
481:
477:
473:
463:
459:
457:
453:
449:
445:
441:
437:
433:
430:Curares like
428:
426:
422:
418:
417:toxicological
414:
410:
406:
402:
393:
391:
387:
384:
379:
377:
373:
369:
365:
361:
357:
353:
352:
347:
346:
341:
337:
333:
319:
318:
315:
308:
299:
298:
295:
288:
281:
277:
276:
274:
271:
266:
259:
257:
253:
226:
224:
220:
215:
207:
203:
199:
198:
196:
187:
183:
176:
172:
171:
169:
167:
163:
156:
152:
151:
149:
147:
143:
136:
132:
131:
129:
127:
123:
116:
112:
111:
109:
102:
98:
91:
87:
86:
84:
82:
78:
69:
68:
65:
58:
53:
49:
45:
41:
38:Clinical data
36:
32:
27:
19:
4702:Plant toxins
4525:Tubocurarine
4504:
4455:Promegestone
4450:Progesterone
4365:Mecamylamine
4175:Cyclopropane
4165:Coronaridine
4097:Barbiturates
4082:Anatruxonium
4052:α-cobratoxin
3895:Sazetidine A
3815:JNJ-39393406
3805:Ispronicline
3525:
3504:Calcicludine
3494:Calciseptine
3477:Bungarotoxin
3446:Tarichatoxin
3394:Arenobufagin
3358:Tetrodotoxin
3317:Tetrodotoxin
3271:Vanillotoxin
3208:Phaiodotoxin
3111:Invertebrate
3034:Solasodamine
2969:Lotaustralin
2804:Fumonisin B4
2800:Fumonisin B2
2796:Fumonisin B1
2782:Cytochalasin
2684:
2664:
2616:
2602:
2596:Superantigen
2588:
2544:
2432:Streptolysin
2373:
2354:
2335:
2316:
2151:
2147:
2141:
2116:
2112:
2106:
2087:
2081:
2056:
2052:
2046:
2021:
2018:RSC Advances
2017:
2007:
1982:
1978:
1944:
1940:
1934:
1891:
1887:
1877:
1850:
1847:EFSA Journal
1846:
1836:
1825:. Retrieved
1820:
1811:
1786:
1782:
1775:
1756:
1750:
1741:
1735:
1710:
1706:
1696:
1685:. Retrieved
1680:
1677:"Toxiferine"
1671:
1646:
1642:
1636:
1611:
1607:
1601:
1576:
1572:
1566:
1541:
1537:
1531:
1521:, retrieved
1509:
1499:
1464:
1460:
1426:
1420:
1387:
1383:
1339:
1335:
1295:
1265:
1261:
1255:
1220:
1216:
1178:
1172:
1155:
1151:
1141:
1127:
1076:(LD50/ED50)
1029:
1013:even though
1008:
972:
928:
925:Distribution
908:
896:
864:
841:
838:Biosynthesis
806:
742:
722:
693:
646:toxiferine I
581:for several
576:
537:
528:rigor mortis
513:
489:
483:
472:arrow poison
469:
460:
432:tubocurarine
429:
399:
390:tubocurarine
380:
356:arrow poison
349:
343:
335:
331:
330:
175:ChEMBL231047
50:Toxiferine I
47:
18:
4697:Neurotoxins
4630:Pirisudanol
4595:Cyprodenate
4575:Adafenoxate
4490:Surugatoxin
4480:Sevoflurane
4435:Pentolinium
4415:Norketamine
4335:Laudanosine
4265:Erythravine
4255:Encenicline
4240:Dipyrandium
4210:Dextrorphan
4056:α-conotoxin
4015:Antagonists
4000:WAY-317,538
3995:Varenicline
3985:Tropisetron
3975:Tebanicline
3920:SSR-180,711
3885:Rivanicline
3875:Pozanicline
3870:PNU-282,987
3865:PNU-120,596
3860:PHA-709,829
3855:PHA-543,613
3795:Galantamine
3770:Epiboxidine
3765:Epibatidine
3685:Altinicline
3467:Snake venom
3421:Epibatidine
3409:Cinobufagin
3266:Stromatoxin
3213:Imperatoxin
3163:Scyllatoxin
3069:Tagetitoxin
3064:Swainsonine
3054:Solauricine
3019:Solamargine
3014:Scopolamine
3004:Retronecine
2870:Zearalenone
2538:Shiga toxin
2509:Cord factor
2348:Enterotoxin
2343:Alpha toxin
2337:perfringens
2329:Tetanolysin
2307:Clostridium
2244:hepatotoxin
2234:enterotoxin
2224:cardiotoxin
2088:Drug design
1823:(in German)
1268:: 156–179.
1044:intravenous
1036:guinea pigs
1015:elimination
883:secologanin
751:. It has a
724:Neostigmine
560:sodium ions
466:Use/purpose
444:pancuronium
436:anesthetics
407:, Bähr and
376:neostigmine
263: g·mol
55:Identifiers
43:Other names
4671:Categories
4590:Citicoline
4570:Acetyl-coA
4554:Precursors
4530:Vanoxerine
4520:Tropeinium
4505:Toxiferine
4470:Reboxetine
4460:Radafaxine
4405:Neramexane
4395:Mivacurium
4390:Metocurine
4355:Malouetine
4320:Isoflurane
4275:Fazadinium
4270:Esketamine
4250:Doxacurium
4235:Dioscorine
4195:Desflurane
4160:Coclaurine
4092:Atracurium
4077:Amantadine
4067:Alcuronium
3820:Levamisole
3810:Ivermectin
3755:Dianicline
3715:Butinoline
3700:Anatoxin-a
3589:modulators
3499:Taicatoxin
3436:Samandarin
3389:Bufotoxins
3353:Ciguatoxin
3331:Vertebrate
3276:Huwentoxin
3256:Cupiennins
3239:Latrotoxin
3183:Kaliotoxin
3153:Margatoxin
3143:Maurotoxin
3084:Toxalbumin
3074:Tinyatoxin
3059:Strychnine
3044:Solasonine
3039:Solasodine
3024:Solanidine
2944:Falcarinol
2929:Delphinine
2845:Phalloidin
2835:Ochratoxin
2830:Orellanine
2820:Lolitrem B
2787:Ergotamine
2737:Mycotoxins
2581:Mechanisms
2540:/Verotoxin
2477:Exfoliatin
2437:Leukocidin
2254:phototoxin
2249:neurotoxin
1827:2024-06-28
1687:2024-06-27
1523:2024-06-30
1510:StatPearls
1133:References
987:alcuronium
969:Metabolism
939:lipophilic
905:Absorption
879:tryptamine
848:strychnine
844:tryptophan
749:tryptamine
667:alcuronium
630:receptor M
618:(α7 nAChR)
579:antagonist
504:alcuronium
496:anesthetic
452:vecuronium
448:atracurium
440:alcuronium
372:antagonist
332:Toxiferine
268:3D model (
256:Molar mass
155:9M7D9K3OJI
126:ChemSpider
81:CAS Number
64:IUPAC name
23:Toxiferine
4430:Pentamine
4425:Pempidine
4375:Methadone
4370:Memantine
4290:Halothane
4280:Gallamine
4260:Enflurane
4215:Diadonium
4130:Bupropion
3915:SIB-1553A
3910:SIB-1508Y
3900:SB-206553
3725:Carbachol
3705:AR-R17779
3695:Anatabine
3690:Anabasine
3655:A-867,744
3650:A-582,941
3645:A-366,833
3404:Bufotenin
3399:Bufotalin
3369:Amphibian
3312:Saxitoxin
3302:Eledoisin
3297:Conotoxin
3168:Hefutoxin
2984:Oleandrin
2964:Linamarin
2954:Helenalin
2914:Cicutoxin
2909:Chaconine
2889:Amygdalin
2860:Vomitoxin
2810:Gliotoxin
2792:Fumonisin
2745:Aflatoxin
2708:Virulence
2644:Endotoxin
2375:botulinum
2356:difficile
2266:Bacterial
2239:hemotoxin
2229:cytotoxin
2038:2046-2069
1727:1365-3075
1663:1472-0299
1312:0368-1769
1046:(IV) and
1005:Excretion
963:cartilage
803:Analogues
739:Structure
734:Chemistry
413:alkaloids
340:alkaloids
4642:See also
4584:lecithin
4560:prodrugs
4510:Tramadol
4360:ME-18-MC
4325:Ketamine
4315:Ibogaine
4135:BW284C51
3890:RJR-2429
3880:Pyrantel
3840:Nicotine
3835:Morantel
3825:Lobeline
3790:EVP-6124
3785:EVP-4473
3740:Cytisine
3735:Cotinine
3640:A-84,543
3611:Agonists
3544:Category
3307:Onchidal
3287:Mollusca
3198:Bestoxin
3193:Birtoxin
3158:Slotoxin
3148:Agitoxin
3123:Scorpion
3079:Tomatine
3029:Solanine
2974:Mimosine
2949:Gossypol
2934:Divicine
2899:Antiarin
2894:Anisatin
2825:Muscimol
2777:Citrinin
2750:Amatoxin
2696:Cry34Ab1
2624:AB toxin
2618:type III
2530:negative
2288:positive
2277:Exotoxin
2133:13701839
1961:18033585
1926:35794473
1803:15519170
1518:30521249
1491:25192059
1412:15302523
1366:16402115
1247:14848460
1070:(μg/kg)
1064:(μg/kg)
949:and the
639:0.5,diss
598:Compound
520:glycogen
510:Efficacy
383:calabash
4580:Choline
4140:BW-A444
4118:(e.g.,
4111:BNC-210
4099:(e.g.,
4062:ABT-126
4046:(e.g.,
4005:XY-4083
3970:TC-6683
3965:TC-5619
3960:TC-5214
3955:TC-2216
3950:TC-1827
3945:TC-1734
3940:TC-1698
3850:NS-1738
3844:tobacco
3730:Choline
3675:ABT-894
3670:ABT-560
3665:ABT-418
3660:ABT-202
3462:Reptile
2924:Daphnin
2919:Coniine
2904:Brucine
2865:Zeranol
2840:Patulin
2687:toxins
2677:Cry3Bb1
2657:Lipid A
2604:type II
2545:E. coli
2297:Bacilli
2156:Bibcode
2073:4245935
1999:5041048
1917:9300463
1896:Bibcode
1868:7153348
1681:PubChem
1628:5032074
1593:7432253
1558:5156145
1482:4176391
1392:Bibcode
1384:Toxicon
1357:1760749
1238:1509221
1122:<15
983:allylic
757:monomer
753:dimeric
690:Binding
550:on the
476:curares
425:potency
405:Wieland
396:History
370:(AChR)
261:614.834
223:Formula
135:4444760
115:5281411
101:PubChem
4170:Curare
4087:AQW051
4034:18-MAC
3990:UB-165
3800:GTS-21
3630:5-HIAA
3598:nAChRs
3334:toxins
3229:Spider
3203:BmKAEP
3173:HgeTx1
3114:toxins
2989:Persin
2882:toxins
2710:factor
2691:Cry6Aa
2683:Other
2672:Cry1Ac
2590:type I
2393:Other:
2318:tetani
2268:toxins
2219:Toxins
2176:816038
2174:
2131:
2094:
2071:
2036:
1997:
1959:
1924:
1914:
1888:Nature
1865:
1801:
1763:
1744:: 242.
1725:
1661:
1626:
1591:
1556:
1516:
1489:
1479:
1433:
1410:
1364:
1354:
1310:
1245:
1235:
1189:
1102:<5
1019:kidney
995:methyl
919:plasma
911:orally
409:Witkop
401:Curare
386:curare
294:SMILES
166:ChEMBL
4558:(and
4540:Xenon
4039:18-MC
4018:(and
3614:(and
3261:PhTx3
3178:HsTx1
3101:Tutin
3094:Ricin
3089:Abrin
2959:Ledol
2880:Plant
2472:delta
2420:Cocci
2381:Botox
1742:Kazan
1119:1.89
1116:2.74
1113:17.8
1099:1.33
1096:1.61
1011:urine
979:liver
676:4100
654:9500
641:(nM)
314:InChI
270:JSmol
4220:DHβE
4021:NAMs
3617:PAMs
3343:Fish
3251:CSTX
2528:Gram
2468:beta
2286:Gram
2172:PMID
2129:PMID
2092:ISBN
2069:PMID
2034:ISSN
1995:PMID
1957:PMID
1922:PMID
1799:PMID
1761:ISBN
1723:ISSN
1659:ISSN
1624:PMID
1589:PMID
1554:PMID
1514:PMID
1487:PMID
1431:ISBN
1408:PMID
1362:PMID
1308:ISSN
1243:PMID
1187:ISBN
1110:6.5
1093:8.9
1090:5.5
1068:LD50
1062:ED50
1040:mice
1038:and
961:and
931:rats
899:ADME
893:ADME
829:and
671:234
624:(nM)
611:(nM)
542:, a
522:and
488:and
450:and
419:and
348:and
146:UNII
3218:Pi3
3188:Lq2
2628:AB5
2164:doi
2121:doi
2061:doi
2026:doi
1987:doi
1949:doi
1912:PMC
1904:doi
1892:607
1863:PMC
1855:doi
1791:doi
1715:doi
1651:doi
1616:doi
1581:doi
1546:doi
1477:PMC
1469:doi
1400:doi
1352:PMC
1344:doi
1340:147
1300:doi
1270:doi
1266:547
1233:PMC
1225:doi
1183:330
1160:doi
1156:228
1107:IM
1087:IV
1042:by
702:by
659:96
649:14
524:ATP
478:by
191:EPA
105:CID
4673::
4122:,
4103:,
4054:,
4050:,
2798:,
2764:,
2760:,
2756:,
2170:.
2162:.
2152:35
2150:.
2127:.
2115:.
2067:.
2057:10
2055:.
2032:.
2020:.
2016:.
1993:.
1981:.
1969:^
1955:.
1945:24
1943:.
1920:.
1910:.
1902:.
1890:.
1886:.
1861:.
1851:15
1849:.
1845:.
1819:.
1797:.
1787:12
1785:.
1721:.
1711:67
1705:.
1679:.
1657:.
1645:.
1622:.
1612:44
1610:.
1587:.
1575:.
1552:.
1542:14
1540:.
1508:,
1485:.
1475:.
1465:77
1463:.
1459:.
1445:^
1406:.
1398:.
1388:44
1386:.
1374:^
1360:.
1350:.
1338:.
1334:.
1320:^
1306:.
1294:.
1282:^
1264:.
1241:.
1231:.
1219:.
1215:.
1201:^
1185:.
1154:.
1150:.
1034:,
889:.
795:Cl
785:46
781:40
769:46
765:40
681:2
637:EC
622:50
620:IC
589::
446:,
442:,
427:.
378:.
237:46
231:40
4586:)
4582:(
4562:)
4126:)
4107:)
4027:)
3846:)
3842:(
3623:)
3578:e
3571:t
3564:v
3469::
3464:/
3371::
3345::
3289::
3231::
3125::
2806:)
2794:(
2768:)
2752:(
2626:/
2554:/
2470:/
2466:/
2367:B
2362:A
2309::
2209:e
2202:t
2195:v
2178:.
2166::
2158::
2135:.
2123::
2117:8
2100:.
2075:.
2063::
2040:.
2028::
2022:6
2001:.
1989::
1983:2
1963:.
1951::
1928:.
1906::
1898::
1871:.
1857::
1830:.
1805:.
1793::
1769:.
1729:.
1717::
1690:.
1665:.
1653::
1647:6
1630:.
1618::
1595:.
1583::
1577:6
1560:.
1548::
1493:.
1471::
1439:.
1414:.
1402::
1394::
1368:.
1346::
1314:.
1302::
1276:.
1272::
1249:.
1227::
1221:6
1195:.
1166:.
1162::
797:2
793:2
791:O
789:4
787:N
783:H
777:2
775:O
773:4
771:N
767:H
632:2
609:i
607:K
272:)
249:2
246:O
243:4
240:N
234:H
228:C
193:)
189:(
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