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Publication Title | THE ACTIVE PRINCIPLES OF CANNABIS INDICA RESIN

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XIV. THE ACTIVE PRINCIPLES OF CANNABIS INDICA RESIN. I

BY THOMAS SPENCE WORK, FRANZ BERGEL AND ALEXANDER ROBERTUS TODD

From the Biochemical Department, Lister Institute, London

(Received24November1938)

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 pre- paration. ExtractsoftheflowershavebeenusedinEuropeanmedicinetosome 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 throughitsuseasadruginorientalcountriesandrecently,pnderthename of "marihuana",itsusehasassumeddangerousproportionsinAmerica. 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 cannabinolwaslaterfoundbythesameworkers[1899]tobeamixture,andthe name cannabinolwastransferredtothatportionoftheactiveresinyieldinga

crystallineacetate,M.P.75°. A gooddealofconfusionwasintroducedbylater 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 con- stitution 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.

Me

(CH2)4Me

M

I

In his last communication Cahn states that " cannabinol is not the pharma- cologically active principle of Cannabis indica" [1933]. It seemed desirable that further investigations on the resin should be made and we have taken up thestudyofcannabisresinwithaviewtoisolatingthesubstanceorsubstances responsibleforitspharmacologicalaction.

The starting point in these investigations was material which corresponded to the high-boiling resin (B.P. 265°/20 mm.) first described by Wood Spivey & Easterfield[1896]. Itwasfoundthatcannabinolcanberemovedalmostquanti- tativelyasitscrystallinep-nitrobenzoate(amountingto25% ofthewhole)on

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