12-05336. Kurchessine [Archived]

Nomenclature

CAS number: 6869-45-0
(3β,20S)-N,N,N′,N′-Tetramethylpregn-5-ene-3,20-diamine; 3β,20α-bis(dimethylamino)-5-pregnene.
C25H44N2; mol wt 372.63.
C 80.58%, H 11.90%, N 7.52%.

Description and references

A steroidal alkaloid from Kurchi bark. Isoln from Holarrhena antidysenterica Wall., Apocynaceae: Tschesche, Otto, Ber. 95, 1144 (1962); Labler, Sorm, Collect. Czech. Chem. Commun. 28, 2345 (1963). Synthesis by methylation of kurchamine: Tschesche, Wiensz, Ber. 91, 1504 (1958). Structure: Labler, Sorm, loc. cit. Possible identity with sarcodinine from Saracococa pruniformis Lindl., Euphorbiaceae: Chatterjee et al., Tetrahedron Lett. 1965, 67. Related alkaloids, kurchiline, kurchiphylline, kurchiphyllamine, from Kurchi leaves: Janot et al., Bull. Soc. Chim. Fr. 1964, 2158.

Chemical structure

Properties

Needles. mp 140-141° (from acetone). [α]D20 37° (c = 1.9); [α]D22 36° (c = 1.112 in CHCl3); [α]D22 17° (c = 1.050 in methanol).

Status

This monograph has been retired and is no longer subject to revision or update.