8. The alkaloids of Ormosia dasycarpa jacks

Journal of the Chemical Society (Resumed)
1960.0

Abstract

The alkaloids of Ormosia dasycarpa Jacks were re-examined. Exhaustive extraction of powdered seeds with boiling methanol gave an alkaloid fraction from which (-)-sparteine was isolated; Hess and Merck may have failed to isolate sparteine due to their use of ethanol. Two new alkaloids were isolated and characterised: dasycarpine, the major alkaloid, which is homogeneous by paper chromatography, has a likely molecular formula of C₂₀H₃₃N₃, contains no N-methyl group but at least one secondary amino-group (evidenced by infrared absorption), and forms a tripicrate, trihydrobromide, and triperchlorate (differing from panamine which forms derivatives with two mols of picric and perchloric acid); and Alkaloid I, which crystallises from ethanol-ether in needles, has [α]ᴅ²⁰ +25.3° (c 1.0 in chloroform), melts at 205-207℃, has the composition C₂₀H₃₅O₃N₃, and is not identical with ormosinine.

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