9949. Veralkamine

Nomenclature

CAS number: 17155-31-6
(3β,16β,17α,22α)-17-Methyl-18-nor-16,28-secosolanida-5,12-diene-3,16-diol; 17-methyl-20α-((2S,5S)-5-methyl-2-piperidyl)-18-nor-17α-pregna-5,12-diene-3β,16β-diol; (22S:25S)-12,26-epimino-17β-methyl-18-norcholesta-5,12-diene-3β,16β-diol; (17S:12S:25S)-22,26-epimino-18(13→17)-abeo-cholesta-5,12-diene-3β,16β-diol; veralcamine.
C27H43NO2; mol wt 413.64.
C 78.40%, H 10.48%, N 3.39%, O 7.74%.

Description and references

Steroidal alkaloid isolated from Veratrum album sp. lobelianium (Bernh.) Suessenguth, Liliaceae: Tomko et al., Pharm. Zentralhalle 99, 373 (1960), C.A. 55, 2013e. Structure studies: Tomko et al., Collect. Czech. Chem. Commun. 27, 1404 (1962). Complete structure: Tomko et al., Tetrahedron Lett. 1967, 3907; eidem, Tetrahedron 24, 4865 (1968); Hoehne et al., ibid. 4875.

Chemical structure

Properties

Crystals from ethanol, mp 119-123° and 165-169°; [α]D24 84.1 ±3° (c = 0.533 in CHCl3).

Derivative

N,O,O-Triacetate.

Properties

mp 152-154°. [α]D27 8.0° (CHCl3).

Derivative

N-Monoacetate.

Properties

mp 191-193°. [α]D23 79.1° (CHCl3).