Oenanthotoxin

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Oenanthotoxin
Oenanthotoxin-structure.png
Identifiers
CAS number 20311-78-8 YesY
PubChem 6436464
ChemSpider 24616929
KEGG C20044
ChEMBL CHEMBL550225
Jmol-3D images Image 1
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 (77 °F), 100 kPa)
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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] A case has been made for the presence of this toxin in local Oenanthe species playing a causative role in euthanasia in ancient Sardinia.[2][3] It was crystallized in 1949 by Clarke and co-workers.[4] It is structurally closely related to the toxins cicutoxin[5] and carotatoxin.[6][7]

References[edit]

  1. ^ Schep, L. J.; Slaughter, R. J.; Becket, G.; Beasley, D. M. G. (2009). "Poisoning due to Water Hemlock". Clinical Toxicology 47 (4): 270–278. doi:10.1080/15563650902904332. PMID 19514873.  edit
  2. ^ Appendino, G.; Pollastro, F.; Verotta, L.; Ballero, M.; Romano, A.; Wyrembek, P.; Szczuraszek, K.; Mozrzymas, J. W.; Taglialatela-Scafati, O. (2009). "Polyacetylenes From Sardinian Oenanthe fistulosa: A Molecular Clue to risus sardonicus". Journal of Natural Products 72 (5): 962–965. doi:10.1021/np8007717. PMC 2685611. PMID 19245244.  edit
  3. ^ Choi, C. Q.; Harmon, K.; Matson, J. (August 2009). "News Scan Briefs: Killer Smile". Scientific American. 
  4. ^ E. G. C. Clarke, D. E. Kidder and W. D. Robertson (1949) J. Pharm. Pharmacol. 1 377-381.
  5. ^ Anet, E. F. L. J.; Lythgoe, B.; Silk, M. H.; Trippett, S. (1953). "Oenanthotoxin and Cicutoxin. Isolation and Structures". Journal of the Chemical Society 1953: 309–322. doi:10.1039/JR9530000309. 
  6. ^ King, L. A.; Lewis, M. J.; Parry, D.; Twitchett, P. J.; Kilner, E. A. (1985). "Identification of Oenanthotoxin and Related Compounds in Hemlock Water Dropwort Poisoning". Human Toxicology 4 (4): 355–364. doi:10.1177/096032718500400401. PMID 4018815. 
  7. ^ Anet, E. F. L. J.; Lythgoe, B.; Silk, M. H.; Trippett, S. (1952). "The Chemistry of Oenanthotoxin and Cicutoxin". Chemistry and Industry 31: 757–758.