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A New Strychnos Alkaloid

1950; Nature Portfolio; Volume: 166; Issue: 4220 Linguagem: Inglês

10.1038/166476a0

1476-4687

F. A. L. Anet, GK Hughes, E Ritchie,

Chemical synthesis and alkaloids

As part of a survey of the chemical constituents of the Australian flora, we have examined the alkaloids of Strychnos psilosperma F. Muell. Leaves collected at Dalmar, near Rockhampton, contained approximately 1 per cent total alkaloid from which a new alkaloid, now named ‘strychnospermine’, was readily isolated. It formed colourless needles of melting point 209°, had [α]D + 58° (c = 2.07 per cent in chloroform), and analyses of it, its bromo-derivative (m.p. 245°), its hydrochloride (m.p. 330–332° with decomp.) and its picrate (m.p. 254° with decomp.) indicated the formula C21H28O3N2. Tests for a methylene-dioxy group were negative, but one methoxyl and one methylimino group were present. When a small crystal of potassium dichromate was added to its solution in cold concentrated sulphuric acid, an intense permanganate colour was immediately produced. Treatment of the alkaloid with methyl iodide at room temperature readily gave a methiodide (m.p. 335° with decomp.), showing the presence of a tertiary nitrogen atom. Strychnospermine could not be hydrogenated in acetic acid solution in the presence of palladium charcoal. Hydrolysis with acid or alkali yielded deacetyl-strychnospermine (m.p. 222°), which was smoothly reconverted to the parent alkaloid by acetic anhydride. The deacetyl derivative gave with nitrous acid a pale yellow crystalline nitroso compound (m.p. c. 195° with decomp.). The remaining oxygen atom is inert and is presumably in an ether linkage.