Oenanthotoxin
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| Oenanthotoxin | |
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(2E,8E,10E,14R)-heptadeca-2,8,10-triene-4,6-diyne-1,14-diol |
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Other names
Enanthotoxin |
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| Identifiers | |
| CAS number | 20311-78-8  |
| PubChem | 6436464 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C17H22O2 |
| Molar mass | 258.355 g/mol |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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] This toxin supposedly played some role in killings in ancient Sardinia.[2] It 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[4] and carotatoxin.[5][6]
[edit] References
- ^ 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.
- ^ Choi, C. Q.; Harmon, K.; Matson, J. (August 2009). "News Scan Briefs: Killer Smile". Scientific American. http://www.scientificamerican.com/article.cfm?id=in-brief-aug-09.
- ^ Appendino, G.; Pollastro, F.; Verotta, L.; Ballero, M.; Romano, A.; Wyrembek, P.; Szczuraszek, K.; Mozrzymas, J. W. et al (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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2685611.
- ^ Anet, E. F. L. J.; Lythgoe, B.; Silk, M. H.; Trippett, S. (1953). "Oenanthotoxin and Cicutoxin. Isolation and Structures". Journal of the Chemical Society: 309–322. doi:10.1039/JR9530000309.
- ^ 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.
- ^ 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.
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