Synthesis and pharmacology of the isomeric methylheptyl-Δ8-tetrahydrocannabinols

Article abstract of DOI:10.1016/S0968-0896(98)80014-X

The synthesis of the 3-heptyl, and the eleven isomeric 3-methylheptyl-Δ⁸-tetrahydrocannabinols (3-7, R and S methyl epimers, and 8) has been carried out. The synthetic approach entailed the synthesis of substituted resorcinols, which were subjected to acid catalyzed condensation with trans-para-menthadienol to provide the Δ⁸-THC analogue. The 1'-, 2'- and 3'-methylheptyl analogues (3-5) are considerably more potent than Δ⁸-THC. The 4'-, 5'- and 6'-methylheptyl isomers (6-8) are approximately equal in potency to Δ⁸-THC. Copyright (C) 1998 Elsevier Science Ltd.