CBH17NO4

BERBERINE  , an alkaloid occurring together with the alkaloids oxyacanthine C16H19NO3, berbamine C13H19NO3, hydrastine C21H21N06, and canadine C20H21NO4, in Berberis vulgaris; it also occurs in other plants, Berberis aristata, B. aquifolium, Hydrastis canadensis, &c . It is a yellow, crystalline solid, insoluble in ether and chloroform, soluble in 41 parts of water at 2 1°, and moderately soluble in alcohol . It is a monacid base; the hydrochloride, C2BH17NO4•HCI, is insoluble in cold alcohol, ether and chloroform, and soluble in 500 parts of water; the acid sulphate, C20H17N04•112SO4, dissolves in about loo parts of water . Canadine is a tetrahydroberberine . Its constitution was worked out by W . H . Perkin (J.C.S., 1889, 55, p . 63; 189o, 57, p . 991) . This followed from a study of the decomposition products, there being obtained hemipinic acid (CH3O)2C6H2(000H)2, and a substance which proved to be to- amino -ethyl- piperonyl carboxylic acid, CH2O2:C6H2•COOH•CH2•CH2NH2 . His formula was modified by Gadamer (Abs . J.C.S., 1902, I, p .

555), who made the

free base an aldehyde, but the salts of an iso-quinolinium type . This formula, which necessitates the presence of two asymmetric carbon atoms in an alkyl tetrahydroberberine, has been accepted by M . Freund and F . Mayer (Abs . J.C.S., 1907, I, p . 632), who showed that two racemic propyl tetrahydroberberines are produced when propyl dihydroberberine is reduced .