Geissospermine

Title: Geissospermine
CAS Registry Number: 427-01-0
CAS Name: (16R,19E)-19,20-Didehydro-16-[(10b,13b,21b)-23-deoxy-21,22-dihydro-11-oxa-12,14-secostrychnidin-10-yl]corynan-17-oic acid methyl ester
Additional Names: 19,20-didehydro-16-(15-ethyl-3a,5,5a,7,8,13a-hexahydro-4H-4,6-ethano-1H,3H-[1,3]oxazino[3,4,5-lm]pyrrolo[2,3-d]carbazol-1-yl)-corynan-17-oic acid methyl ester; b,17-epoxy-a-(3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindole[2,3-a]quinolizin-2-yl)-curan-1-propanoic acid methyl ester
Molecular Formula: C40H48N4O3
Molecular Weight: 632.83
Percent Composition: C 75.92%, H 7.65%, N 8.85%, O 7.58%
Literature References: From bark of Geissospermum vellosii Allem., Apocynaceae: Hesse, Ann. 202, 141 (1880). Structure: Puisieux, LeHir, Compt. Rend. 252, 902 (1961); Janot, Tetrahedron 14, 113 (1961). Crystal structure: A. Chiaroni, C. Riche, Acta Crystallogr. 35B, 1820 (1979). Pharmacology: M. M. Aurousseau, Ann. Pharm. Fr. 19, 175 (1961). On hydrolysis with HCl splits into geissoschizine and geissoschizoline, q.v.
Properties: Anhydr form, crystals from abs acetone, mp 213-214° (dec). [a]D20 -101° (ethanol). uv max (methanol): 251, 285, 293 nm (log e 4.10, 3.91, 3.90). Slightly sol in water, ether; sol in alcohol.
Melting point: mp 213-214° (dec)
Optical Rotation: [a]D20 -101° (ethanol)
Absorption maximum: uv max (methanol): 251, 285, 293 nm (log e 4.10, 3.91, 3.90)
Derivative Type: Dihydrate
Properties: mp 207° (sinters at 145°).
Melting point: mp 207° (sinters at 145°)
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