LXXXVI.—Cannabis Indica resin. Part II

Abstract
The active principle of C. indica resin (hashish, etc.) is contained in a high-boiling resin, from which cannabinol (I), trinitrocannabinol (II), a hydrocarbon (III), and nitrocannabinolactone (IV) (c. f. Part I), have been prepared. The statements of Wood, Spivey and Easterfield (1899) on the isolation of I are confirmed. "Crude cannabinol" is ether-soluble, and, when treated with acetyl chloride in pyridine, yields a crystalline acetylcannabinol, C21H25O2AC, which on hydrolysis affords pure cannabinol (uncrystallisable). The cannabinol, unless prepared from the acetyl derivative, is a mixture. Nitration of cannabinol with cold fuming nitric acid yields II, oxidized by hot nitric acid to IV. II forms a methyl ether, most conveniently prepared with dry methyl iodide and silver oxide in absence of a solvent, and hydrolyzed by warm pyridine and a little water or by piperidine, showing that methylation occurs at the hydroxyl group. II contains 2 benzene nuclei, one in the residue giving IV, the other carrying 2 nitro-groups and a phenolic hydroxyl group. The objection of Bergel to the structure previously proposed for IV is refuted. The main constituent of III is probably n-nonacosane.