Oenanthotoxin

Oenanthotoxin
Oenanthotoxin
IUPAC name
(2E,8E,10E,14R)-heptadeca-2,8,10-triene-4,6-diyne-1,14-diol
Other names
Enanthotoxin
Identifiers
CAS number 20311-78-8
PubChem 6436464
Jmol-3D images Image 1
Properties
Molecular formula C17H22O2
Molar mass 258.355 g/mol
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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[2]. 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.).[3] It is structurally closely related to the toxins cicutoxin and carotatoxin.[4][5][6]


References

  1. ^ http://www.informapharmascience.com/doi/abs/10.1080/15563650902904332
  2. ^ 'Killer Smile', News Scan Briefs,Scientific American, August 2009 "News Scan Briefs". http://www.scientificamerican.com/article.cfm?id=in-brief-aug-09. 
  3. ^ Polyacetylenes from Sardinian Oenanthe fistulosa: A Molecular Clue to risus sardonicus
  4. ^ 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. 
  5. ^ 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. PMID 4018815. 
  6. ^ 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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