3569. Enanthotoxin

Nomenclature

CAS number: 20311-78-8
(2E,8E,10E)-2,8,10-Heptadecatriene-4,6-diyne-1,14-diol; oenanthotoxin.
C17H22O2; mol wt 258.36.
C 79.03%, H 8.58%, O 12.39%.

Description and references

The poisonous principle of Oenanthe crocata L., Umbelliferae, the hemlock water dropwort, a toxic plant known since 1746 and believed to be the most poisonous plant in England. Isoln: Clarke et al., J. Pharm. Pharmacol. 1, 377 (1949). Structure studies: Anet et al., Chem. Ind. (London) 1952, 757; J. Chem. Soc. 1953, 309. Synthesis of dl-form: Bohlmann, Viehe, Ber. 88, 1245 (1955). Fluorimetric determn: B. Del Castillo et al., Ital. J. Biochem. 29, 233 (1980). Blocking of sodium current and intramembrane charge movement: J. M. Dubois, M. F. Schneider, Nature 289, 685 (1981); eidem, Toxicon 20, 49 (1982). Toxicity study: M. P. Martinez-Honduvilla et al., Arch. Farmacol. Toxicol. 7, 197 (1981).

Chemical structure

Properties

Large prisms (natural) or star-shaped crystals (synthetic). Unstable, dec by light and air to brown insol resin. mp 87° (natural), 68° (synthetic). [α]D15 +30.5° (c = 2.0 in methanol). uv max: 213, 252, 267, 281, 296, 315.5, 337.5 (ε × 10-3 17.5, 33, 29, 17.5, 30.5, 40, 29). Practically insol in water, petr ether, alkalies, dil mineral acids. Readily sol in chloroform, ethanol, methanol, ether, benzene. Average LD i.p. in mice: 0.83 mg/kg (Clarke). LD50 i.p. in rats: 2.94 mg/kg (Martinez-Honduvilla).

Caution

Very toxic. May cause convulsions, death.