Vomicine

Vomicine, This alkaloid, obtained from residues of... 

Analogues of vomicidine are produced by the electrolytic reduction of proximate derivatives of vomicine, still containing the lactam group, e.g., isoVomicine, C22H24O4N2 isovomicidine, C22H2SO3N2, m.p. 290° (dec.) (Part XXVII). 

Exhaustive Methylation. (Parts I, XXII, XXVIII>) This process applied to vomicine has developed difficulties like those met with in the case of strychnine (p. 575). The Emde process used with vomicine metlio-sulphate, C22H24O4N2. MeHS04, m.p. 272° (dec.), produced two methyl-vomicihes, I and II, C23H28O4N2. 

Oxidation of Vpmicine. On oxidation with chromic acid, vomicine yields three acids (Parts I, IX, XII and XXIII) —... 

The chemistry of vomicine is dealt with in a series of papers by Wieland and collaborators published in LiMg s Annalen. These parts are referred to in the text of the article where necessary. Part I (with Oertei.), 1929, 469, 198 VI, VII, VIII (with CA1.TET and Moyer), 1981, 491, 107, 117, 129 EX, X (with HfimcBEB and... 

Of the other Strychnos alkaloids vomicine has been investigated by Ruickoldt, who finds that in mice and rabbits it causes clonic convulsions, due to stimulation above the level of the anterior corpore quad-ragemina. Convulsions can be elicited after intravenous, but not after subcutaneous, injections. The toxicity is low twelve times the convulsive dose does not cause death. No special action is exerted on blood... 

Vomicidine and derivatives, 591, 592 oxidation, 594 Vomicine, 553, 586, 589, 592 constitution, 586 exhaustive methylation, 592 oxidation, 594 pharmacological action, 596 reduction products, 589 and derivatives, formhlae, 587, 593, 595... 

Strychnos pierriana L. Ma Qian Zi (seed) Strychnine, brucine, vomicine, pseudostrychnine, pseudobrucine, novacine.33 Increase central nervous system reflex stimulation. 

New extractions of the leaves of S. icaja, also from Zaire, have resulted in the isolation of seven known alkaloids, together with novacine (184), also known, but not hitherto reported to occur in this species.106 A ninth alkaloid is new, and appears to be 19,20-a-epoxy-12,15-dihydro-l 1-methoxy-Nb-methyl sec.-pseudostrychnine (185). The leaves of a specimen of this same plant from Cameroun contained four known alkaloids, plus a new one, 19,20-a -epoxy-11,12-dimethoxy-iVb-methyl see.-pseudostrychnine (186). The fruits of a Gabonese sample, which had reputedly been exhibited at the Paris Colonial Exhibition of 1889, contained eight alkaloids, namely icajine, vomicine, 19,20-a-epoxynovacine, 19,20-a-epoxy-12,1 5-dihydroxy-Nb-methyl sec.-pseudostrychnine (187), and the related bases (185) and (188)—(190), of which (190) was the major constituent.106... 

Two nine-stage procedures have been developed840 for the conversion of strychnine into vomicine (165) these serve to confirm the structure, on which little work appears to have been done since the structure determination by Bailey and Robinson.84 ... 

Depending on the reaction medium some cyclic alkaloids behave as ring enlarged or as ring contracted compounds. In Scheme VIII/19 indole alkaloids vomicine and perivine, the isoquinoline alkaloid protopine, and pyrrolizidines are given with their ring contracted forms. 

That vomicine contains a phenolic hydroxyl group is not immediately obvious, for the alkaloid is insoluble in alcoholic alkali, does not give a ferric chloride color, and is not easily methylated or acetylated on the phenolic oxygen (187). Later work led to the isolation of what may be O-methylvomicine in small yield (191) and to O-acetylvomicine by the action of acetic anhydride sodium acetate (192). The presence of a phenolic grouping is evident, however, in vomicinic acid (CCXXXVIII ... 

Vomicine is easily monobrominated, probably in position 3, ortho to the phenolic group (187). Mononitration may be achieved with dilute aqueous nitric acid, but is difficult and gives varying yields dihydro-vomicine on the other hand gives a dinitro derivative in very good yield (194). Nitric-concentrated sulfuric acid mixture at —18° oxidizes the aromatic ring (see Section IV, E, 2). 

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