Veralkamine
Title: Veralkamine
CAS Registry Number: 17155-31-6
CAS Name: (3b,16b,17a,22a)-17-Methyl-18-nor-16,28-secosolanida-5,12-diene-3,16-diol
Additional Names: 17-methyl-20a-((2S,5S)-5-methyl-2-piperidyl)-18-nor-17a-pregna-5,12-diene-3b,16b-diol; (22S:25S)-12,26-epimino-17b-methyl-18-norcholesta-5,12-diene-3b,16b-diol; (17S:12S:25S)-22,26-epimino-18(13®17)-abeo-cholesta-5,12-diene-3b,16b-diol; veralcamine
Molecular Formula: C27H43NO2
Molecular Weight: 413.64
Percent Composition: C 78.40%, H 10.48%, N 3.39%, O 7.74%
Literature 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.
Properties: Crystals from ethanol, mp 119-123° and 165-169°; [a]D24 -84.1 ±3° (c = 0.533 in CHCl3).
Melting point: mp 119-123° and 165-169°
Optical Rotation: [a]D24 -84.1 ±3° (c = 0.533 in CHCl3)
 
Derivative Type: N,O,O-Triacetate
Properties: mp 152-154°. [a]D27 -8.0° (CHCl3).
Melting point: mp 152-154°
Optical Rotation: [a]D27 -8.0° (CHCl3)
 
Derivative Type: N-Monoacetate
Properties: mp 191-193°. [a]D23 -79.1° (CHCl3).
Melting point: mp 191-193°
Optical Rotation: [a]D23 -79.1° (CHCl3)

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