Funtumine

Title: Funtumine
CAS Registry Number: 474-45-3
CAS Name: (3a,5a)-3-Aminopregnan-20-one
Additional Names: 3a-amino-20-oxo-5a-pregnane
Molecular Formula: C21H35NO
Molecular Weight: 317.51
Percent Composition: C 79.44%, H 11.11%, N 4.41%, O 5.04%
Literature 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).
Properties: Prisms from ethyl acetate, mp 126°. [a]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).
Melting point: mp 126°
pKa: pK 9.18
Optical Rotation: [a]D +95° (c = 1.7 in chloroform)
Toxicity data: LD50 i.v. in mice: 30 mg/kg (Lacassagne)
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