The active principles of Cannabis indica resin. I.
THE resinous exudate of the female flowers of Cannabis indica (C. sativa) forms the essential constituent of the drug variously known as hashish, bhang, charas, ganja and marihuana according to the country of origin and mode of preparation. Extracts of the flowers have been used in European medicine to some extent but were found to be so variable in activity that C. indica has been removed from the British Pharmacopoeia. The plant is, however, well known through its use as a drug in oriental countries and recently, pnder the name of "marihuana ", its use has assumed dangerous proportions in America. Cannabis resin has been the subject of many investigations in the past but much of the earlier work is contradictory. The active principle is contained in a high-boiling resin and is not an alkaloid [Smith, 1857]. The active fraction isolated from the crude resin by Wood Spivey & Easterfield [1896] and given by them the name cannabinol was later found by the same workers [1899] to be a mixture, and the name cannabinol was transferred to that portion of the active resin yielding a crystalline acetate, M.P. 75°. A good deal of confusion was introduced by later workers, who, although failing to obtain a crystalline acetate, nevertheless applied the name cannabinol to their products. The situation was largely clarified by Cahn [1931], who confirmed the observations of Wood Spivey & Easterfield and established for cannabinol the formula C21H2,O2. The constitution of cannabinol has been investigated by Cahn [1930-33] and by Bergel [1932], and for it the former proposed structure (I) in which only the positions of the hydroxyl and n-amyl groups are to be regarded as uncertain.