• Journal Article

Side chain methyl analogues of Delta(8)-THC

Citation

Huffman, J. W., Lainton, J. A. H., Banner, W. K., Duncan, S. G., Jordan, R. D., Yu, S., ... Compton, D. R. (1997). Side chain methyl analogues of Delta(8)-THC. Tetrahedron, 53(5), 1557-1576.

Abstract

The synthesis of both side chain epimers of 1'- (4), 2'- (5), 3'-methyl- (6) and 4'-methyl-Delta(8)- tetrahydrocannabinol (7) has been carried out. The synthetic approach entailed the acid catalyzed condensation of the appropriate substituted resorcinol with menthadienol to provide the Delta(8)-THC analogue. Both isomers of 1'- (4) and 2'-Delta(8)-THC (5) were more potent than Delta(8)-THC, both in vitro and in vivo. The 3'-methyl isomers (6) were approximately equal in potency to Delta(8)-THC, and 4'-methyl-Delta(8)-THC was less potent. There was relatively little difference in potency between the epimers of 4, 5, and 6. (C) 1997, Elsevier Science Ltd