7415. Picrotoxin

Nomenclature

CAS number: 124-87-8
Cocculin.
C30H34O13; mol wt 602.58.
C 59.80%, H 5.69%, O 34.52%.

Description and references

Bitter principle isolated from the seed of Anamirta cocculus L. Wight & Arn., Menispermaceae, also found in Tinomiscium philippinense Diels. Molecular compd of one mole picrotoxinin and one mole picrotin, q.q.v., into which it is readily separated. Extraction procedure: Clark, J. Am. Chem. Soc. 57, 1111 (1935). Chemical bibliography: Helv. Chim. Acta 32, 1859 (1949). Crystal and molecular structure: L. Dupont et al., Acta Crystallogr. B32, 2987 (1976). Toxicity study: I. Setnikar et al., J. Pharmacol. Exp. Ther. 128, 176 (1960).

Properties

Intensely bitter shiny rhomboid leaflets, mp 203°. Poisonous. [α]D16 -29.3° (c = 4 in abs ethanol). One gram dissolves in ≈350 ml water, in ≈5 ml boiling water, in 13.5 ml 95% ethanol, in ≈3 ml boiling alcohol. Sparingly sol in ether, chloroform. Readily sol in strong ammonia water, in aq solns of NaOH. Highly toxic to fish. LD50 i.p. in mice: 7.2 mg/kg (Setnikar).

Therapeutic Category

CNS and respiratory stimulant.

Therapeutic Category (Veterinary)

CNS stimulant, antidote to barbiturates.

Keywords

CNS Stimulant; Respiratory Stimulant