Preparation of Compounds with Marijuana Activity

Chapter 7 Isomerisation Preparation of Compounds with Marijuana Activity from Cannabidiol 

It has now been found that cannabidiol isomerizes upon treatment, for example, with a variety of reagents such as p-toluenesulfonic acid, sulfuric acid, hydrochloric acid and ethanol, hydrogen chloride in ether, pyridine hydrochloride, sulfamic acid, zinc chloride, ethanolic phosphoric acid, etc. and is converted to tetrahydro cannabinol which has marihuana activity and which may be represented by the following formula, with doubt merely in regard to the position of the double bond in the left-hand cycle. 

The present invention is directed broadly to all materials obtained by isomerization of cannabidiol, the exact position of the double bond in the product being of relatively minor importance. The tetrahydro canabinols obtained are colorless, highly viscous oils, though it is not impossible that eventually when one or more are obtained in absolutely pure state they will be found to be solids. 

The tetrahydro cannabinols form acyl derivatives, such as the monoacetates, and ether-derivatives such as the monomethyl ether, with specific rotations corresponding to the rotation of the tetrahydro cannabinol from which each may be formed. 

When the tetrahydro cannabinols are reduced, regardless of the specific rotation of the initial material used, after absorption of one molecule of hydrogen a hexahydro cannabinol is produced. 

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