The alkaloids of Picralima klaineana, Pierre. Pt. 2 / by T.A. Henry.

  • Henry, Thomas Anderson, 1873-1958.
Date:
[1932]
Catalogue details

Licence: Public Domain Mark

Credit: The alkaloids of Picralima klaineana, Pierre. Pt. 2 / by T.A. Henry. Source: Wellcome Collection.

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    boiling alcohol, in which akuammidine is easily soluble and akuam- mine almost insoluble. The alkaloids remaining in solution in the ether are recovered, dissolved as far as possible in benzene, and isolated by fractional extraction with A7-hydrochloric acid, when the hydrochlorides are removed in the following order : amorphous alkaloid B (ferric chloride test), akuammiline, C22H2404N2, pseud- akuammigine, C22H2603N2, and akuammenine, C20H22O4N2, the last two being isolated as picrates partly from the ultimate acid extracts and partly from the residual benzene solution. Throughout this fractionation of both groups of alkaloids tar separates, and from this by treatment with acetone, akuammigine, C22H2603N2, is obtained as the hydrochloride. The names, extended linear formulae, yields, and typical colour reactions of the nine crystalline alkaloids so far obtained from the seeds are given in the following table. Colour reactions. Yield on A Name. Extended linear formula. seeds, %. Cone. HNOs. Piperonal -f-HCl. Akuammicine* C18H170N2(0Me) 0-0064 | Bright green, be- 1 coming blue on Magenta, chang¬ ing to ultra- Pseudakuammicine C18Hl7ON2(OMe) 0-0037 | 1 dilution with marine blue on Akuammenine Akuammidine* C„H1,OlN,(OMe) CaoH21OjNj(OMe) J 0-0006 0-0340 ' water Yellow ■> standing Akuammigine* C21H„OtN2(OMe) 0-0100 Bright yellow Pseu dakuammigine* C20n20OaN(OMeXNMe) 0-0170 Brown, changing Pink, changing Akuammiline* C2iH2J08N2(0Me) 0-0107 to yellow None 1 >- to amethyst or standing Akuammine* C20H2,O2N(OHXOMe)(NMe) 0-5G00 Blood-red 1 Akuammine hydrate* C20II23O3N(OHXOMeXNMe) — Blood-red / The samples of akuamma seed worked up were usually small and the yields recorded in the table were those obtained from the only large sample, 21 kilog., received from the Gold Coast. With the exception of akuammine, of which about 120 grams have nowT been accumulated for further wTork, only small quantities of these alkaloids, ranging from 0-2 gram of akuammenine to 7*5 grams of akuam¬ midine, w^ere available and consequently nothing but their charac¬ terisation and a few exploratory experiments could be attempted with them. The alkaloids wrhose names are marked with an asterisk in the table all yield crystalline monomethiodides except akuammigine, in which case it is still amorphous. All these metbiodides behave as quaternary iodides, indicating the presence of at least one tertiary nitrogen atom in the parent alkaloid. No evidence that the second nitrogen atom in akuammine is present as an imino-group has been obtained. This base gives a benzoyl derivative, which behaves as a normal O-benzoyl ester, and with nitrous acid it yields nitro- akuammine. Akuammidine also yields a mono benzoyl derivative, but this is neutral in reaction and insoluble in acids and the entering acyl group is apparently attached to a nitrogen atom ; this, however,