Synthesis and pharmacology of the isomeric methylheptyl-Δ8-tetrahydrocannabinols Original Research Article

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.