Some 11-substituted tetrahydrocannabinols. Synthesis and comparison with the potent cannabinoid metabolites 11-hydroxytetrahydrocannabinols

A series of compounds was prepared in which the 11-hydroxyl of 11-hydroxy-delta8-THC, the potent metabolite of delta8-THC, was replaced by a methyl, methyoxy, amino, or acetamido group. All of the compounds tested produced behavioral changes in dogs, but only the methoxy compound has analgesic properties in mice. An isosteric oxime was inactive in mice.