Synthesis and pharmacology of the isomeric methylheptyl-Delta(8)-tetrahydrocannabinols
Huffman, J. W., Liddle, J., Duncan, S. G., Yu, S., Martin, B. R., & Wiley, J. (1998). Synthesis and pharmacology of the isomeric methylheptyl-Delta(8)-tetrahydrocannabinols. Bioorganic and Medicinal Chemistry, 6(12), 2383-2396.
The synthesis of the 3-heptyl, and the eleven isomeric 3-methylheptyl-Delta(8)-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 Delta(8)-THC analogue. The 1'-, 2'- and 3'-methylheptyl analogues (3-5) are considerably more potent than Delta(8)-THC. The 4'-, 5'- and 6'-methylheptyl isomers (6-8) are approximately equal in potency to Delta(8)-THC. (C) 1998 Elsevier Science Ltd. All rights reserved