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Oenanthotoxin
IUPAC name	(2E,8E,10E,14R)-heptadeca-2,8,10-triene-4,6-diyne-1,14-diol
Other names	Enanthotoxin
SMILES	CCC[C@@H](O)CC\C=C\C=C\C#CC#C\C=C\CO
Identifiers
CAS number	20311-78-8
PubChem	6436464
Properties
Molecular formula	C17H22O2
Molar mass	258.355 g/mol
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

Oenanthotoxin is a toxin extracted from hemlock water dropwort (Oenanthe crocata) and other plants of the genus Oenanthe. It is a central nervous system poison, and acts as a noncompetitive gamma-aminobutyric acid antagonist. ^[1] This toxin played some role in euthanasia in ancient Sardinia, for inducing risus (see Scientific American, August 2009). It was first isolated by a Boehm scientist in 1876 and was crystallized in 1949 by E.G.C. Clarke, D.E. Kidder and W.D. Robertson (J. Pharm. Pharmacol.).^[2]^[3] It is structurally closely related to the toxin cicutoxin of water hemlock.^[4]^[5]^[6]

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[edit] References

^ http://www.informapharmascience.com/doi/abs/10.1080/15563650902904332
^ Death by cicutoxin
^ Polyacetylenes from Sardinian Oenanthe fistulosa: A Molecular Clue to risus sardonicus
^ E. Anet, B. Lythgoe, M. H. Silk, S. Trippett (1953). "Oenanthotoxin and cicutoxin. Isolation and structures". Journal of the Chemical Society: 309–322. doi:10.1039/JR9530000309.
^ L. A. King, M. J. Lewis, D. Parry, P. J. Twitchett, E. A. Kilner (1985). "Identification of oenanthotoxin and related compounds in hemlock water dropwort poisoning.". Human Toxicology 4 (4): 355–364. doi:10.1177/096032718500400401.
^ E. Anet, B. Lythgoe, M. H. Silk, S. Trippett (1952). "The Chemistry of Oenanthotoxin and Cicutoxin". Chemistry and Industry 31: 757–758.

[0] ttp://www.informapharmascience.com/doi/abs/10.1080/15563650902904332

[1] Death by cicutoxin

[2] Polyacetylenes from Sardinian Oenanthe fistulosa: A Molecular Clue to risus sardonicus

[3] E. Anet, B. Lythgoe, M. H. Silk, S. Trippett (1953). "Oenanthotoxin and cicutoxin. Isolation and structures". Journal of the Chemical Society: 309–322. doi:10.1039/JR9530000309.

[4] L. A. King, M. J. Lewis, D. Parry, P. J. Twitchett, E. A. Kilner (1985). "Identification of oenanthotoxin and related compounds in hemlock water dropwort poisoning.". Human Toxicology 4 (4): 355–364. doi:10.1177/096032718500400401.

[5] E. Anet, B. Lythgoe, M. H. Silk, S. Trippett (1952). "The Chemistry of Oenanthotoxin and Cicutoxin". Chemistry and Industry 31: 757–758.

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