4292. Funtumine

Nomenclature

CAS number: 474-45-3
(3α,5α)-3-Aminopregnan-20-one; 3α-amino-20-oxo-5α-pregnane.
C21H35NO; mol wt 317.51.
C 79.44%, H 11.11%, N 4.41%, O 5.04%.

Description and references

Steroidal alkaloid isolated from Funtumia latifolia Stapf., Apocynaceae: Janot et al., C. R. Hebd. Seances Acad. Sci. 246, 3076 (1958); from leaves of Holorrhena febrifuga Stapf., Apocynaceae: H. Dodoun et al., Phytochemistry 12, 923 (1973). Structure: Janot et al., Bull. Soc. Chim. Fr. 1960, 1640, 1669. Prepn: H. Kapnang et al., Tetrahedron Lett. 1977, 3469. Review: R. Goutarel, Bull. Soc. Chim. Fr. 1960, 769. Effect on liver carcinogenesis in rats: A. Lacassagne et al., C. R. Seances Acad. Sci. Ser. D 274, 2830 (1972).

Chemical structure

Properties

Prisms from ethyl acetate, mp 126°. [α]D +95° (c = 1.7 in chloroform). pK 9.18. Sol in the usual organic solvents. LD50 i.v. in mice: 30 mg/kg (Lacassagne).