- Histrionicotoxin
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ImageFile=Histrionicotoxin.png
IUPACName=(2S,6R,7S,8S)-7- [(Z)-but-1-en-3-ynyl] -2- [(Z)-pent-2-en-4-ynyl] -1-azaspiro [5.5] undecan-8-ol
OtherNames=Histrionicotoxin
Section1=Chembox Identifiers
CASNo= 34272-51-0
PubChem= 6437364
SMILES= C#CC=C/C [C@@H] 1CCC [C@@] 2(N1)CCC [C@@H] ( [C@H] 2C=C/C#C)O
Section2=Chembox Properties
C=19 | H=25 | N=1 | O=1
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Section3=Chembox Hazards
MainHazards=Toxic
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Autoignition=Histrionicotoxin is one of a number of related toxins found in the skin of
poison frog s from the "Dendrobatidae " family, notably "Dendrobates histrionicus ". [Daly JW. Alkaloids of neotropical poison frogs (Dendrobatidae). "Fortschritte der Chemie Organischer Naturstoffe". 1982;41:205-340. PMID 7049875] It is likely that as with other poison frog alkaloids, histrionicotoxin is not manufactured by the amphibians, but absorbed from insects in their diet and stored in glands in their skin. [Daly JW. The chemistry of poisons in amphibian skin. "Proceedings of the National Academy of Sciences USA". 1995 Jan 3;92(1):9-13. PMID 7816854]Histrionicotoxin is a less powerful toxin compared to many of the other alkaloids found in poison frogs, however it has an unusual chemical structure and a distinct mechanism of action, acting as a potent non-competitive antagonist of
nicotinic acetylcholine receptor s, binding to a regulatory site on the delta subunit of the ion channel complex. [Oberthür W, Muhn P, Baumann H, Lottspeich F, Wittmann-Liebold B, Hucho F. The reaction site of a non-competitive antagonist in the delta-subunit of the nicotinic acetylcholine receptor. "EMBO Journal". 1986 Aug;5(8):1815-9. PMID 3758027] [Johnson DA, Nuss JM. The histrionicotoxin-sensitive ethidium binding site is located outside of the transmembrane domain of the nicotinic acetylcholine receptor: a fluorescence study. "Biochemistry". 1994 Aug 9;33(31):9070-7. PMID 8049208] It also has some affinity for sodium and potassium channels, although it is much less potent for these targets. [Lovenberg T, Daly JW. Histrionicotoxins: effects on binding of radioligands for sodium, potassium, and calcium channels in brain membranes. "Neurochemical Research". 1986 Nov;11(11):1609-21. PMID 2446155] The synthesis of histrionicotoxin and its various homologues is synthetically challenging and has been the subject of many different attempts. [Sinclair A, Stockman RA. Thirty-five years of synthetic studies directed towards the histrionicotoxin family of alkaloids. "Natural Product Reports". 2007 Apr;24(2):298-326. PMID 17389999]References
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