Two new alkaloids, brunsvigine and brunsvinine, are isolated from Brunsvigia cooperi Baker bulbs collected in summer, lycorine replacing brunsvinine in bulbs collected in late autumn. Crinamine is also isolated throughout. Brunsvigine is shown to be isomeric with lycorine, possessing the same groups as the latter, but differing from lycorine in ease of dehydration and in the behaviour of the dihydro-derivative.No member of the Brunsvigz'a genus of the family Amaryllidaceae has so far been examined chemically. Brunsvigia Yosea (Lam.), investigated by Wildman and his co-workers? has been referred back to AmaryZZis rosea ( A . belladonna Linn.2). The bulbs of B. cooperi Baker are now found to contain two new alkaloids: brunsvigine, C,,H,,O,N, as the main alkaloid, and brunsvinine, C,,H1,O,N, in very small quantities in bulbs collected during early summer, becoming replaced, seemingly completely so, by lycorine towards autumn. A fourth alkaloid, identified as crinamine,l,3 was found in more or less constant yield throughout.Ready formation of a methiodide showed the nitrogen to be tertiary. The presence of two hydroxy-groups was shown by formation of diacetylbrunsvigine, and a broad band at 3475 cm.-l in the infrared spectrum of the alkaloid indicated that the hydroxy-groups were associated. That the hydroxy-groups are neighbours was indicated by reaction with one mol. of periodic acid in acid solution although no reaction was observed in neutral medium; according to Price and Knell's findings4 this could mean that the hydroxygroups are trans-oriented. The resulting Oxidation product reduced Fehling's solution but failed to crystallise or to yield a tractable picrate or methiodide. Dihydrobrunsvigine similarly reacted with one mol. of periodic acid but also failed to yield a tractable dialdehyde. I t is of interest that lycorine consumes -1 mol. of periodic acid in acid medium in 6 days, and dihydrolycorine reacts more slowly.Berzoa's test showed the presence of a methylenedioxy-group. Permanganate oxidation of brunsvigine gave a small amount of hydrastic acid.6Catalytic reduction of brunsvigine gave a dihydro-derivative, whose ultraviolet spectrum [ A, , .

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Cassipourine, CI4H2,N2S4, a ditertiary base, gives pyrrolo [1,2-a] pyrrolidine by zinc-dust distillation, and pyrrolizidine by desulphurisation with Raney nickel. Oxidation of cassipourine with hydrogen peroxide gives the di-N-oxide and with concentrated nitric acid pyrrolizidine disulphonic acid N-oxide. The reactions are discussed on the basis of the structure as 1 a,l 'P:2@.2'a-(bisdithiodi-8a-pyrrolizidine) determined by X-ray analysis.

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