4358. Gamabufotalin

Nomenclature

CAS number: 465-11-2
(3β,5β,11α)-3,11,14-Trihydroxybufa-20,22-dienolide; gamabufogenin; gamabufagin.
C24H34O5; mol wt 402.52.
C 71.61%, H 8.51%, O 19.87%.

Description and references

One of the genins found in the venom of a Japanese toad (gama; Bufo vulgaris formosus). Isoln and structure: Kotake, Ann. 465, 11 (1928); Wieland, Vocke, Ann. 481, 215 (1930); Chen et al., J. Pharmacol. Exp. Ther. 49, 26 (1933); Kondo, Ohno, J. Pharm. Soc. Jpn. 59, 186 (1939); Jensen, J. Am. Chem. Soc. 59, 767 (1937); Kuno Meyer, Helv. Chim. Acta 32, 1599 (1949). Also found in Ch'an-Su, A Chinese drug prepared from Chinese toads (Bufo asiaticus = Bufo gargarizans Cantor): Ruckstuhl, Meyer, Helv. Chim. Acta 40, 1270 (1957).

Chemical structure

Properties

Bitter, solvated prisms from alcohol + ether, mp 254°; when dry dec 262-263°. [α]D18 +1.26° (c = 0.793 in methanol). Produces numbness of the tongue. uv max about 300 nm. Very sparingly sol in chloroform, acetone, water. Somewhat more sol in methanol.