Oenanthotoxin

Oenanthotoxin
Names
Preferred IUPAC name
(2E,8E,10E,14R)-Heptadeca-2,8,10-triene-4,6-diyne-1,14-diol
Other names
Enanthotoxin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C17H22O2/c1-2-14-17(19)15-12-10-8-6-4-3-5-7-9-11-13-16-18/h4,6,8,10-11,13,17-19H,2,12,14-16H2,1H3/b6-4+,10-8+,13-11+/t17-/m1/s1 checkY
    Key: UPXPHJXYZGEBCW-SRFVWEJJSA-N checkY
  • InChI=1/C17H22O2/c1-2-14-17(19)15-12-10-8-6-4-3-5-7-9-11-13-16-18/h4,6,8,10-11,13,17-19H,2,12,14-16H2,1H3/b6-4+,10-8+,13-11+/t17-/m1/s1
    Key: UPXPHJXYZGEBCW-SRFVWEJJBP
  • CCC[C@@H](O)CC\C=C\C=C\C#CC#C\C=C\CO
Properties
C17H22O2
Molar mass 258.361 g·mol−1
Melting point 86 °C (187 °F; 359 K)
Hazards
Lethal dose or concentration (LD, LC):
0.58 mg/kg for mice
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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 antagonist of the neurotransmitter gamma-aminobutyric acid.[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] Oenanthotoxin is a C17 polyacetylene isomer of cicutoxin.

  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. S2CID 21855822.
  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.
  3. ^ Choi, C. Q.; Harmon, K.; Matson, J. (August 2009). "News Scan Briefs: Killer Smile". Scientific American. doi:10.1038/scientificamerican0809-26b.
  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. S2CID 19201342.
  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.