ChemInform Abstract: Side Chain Methyl Analogues of Δ8‐THC.

Abstract

Side Chain Methyl Analogues of ∆8-THC. -In view of the interest to investigate the effect of the variation of the cannabinoid side chain upon the potency the compounds (I) are synthesized by acid catalyzed condensation of the appropriate substituted resorcinols with menthadienol. This methodology is also extended to nonracemic compounds. Both isomers of (Ia) and (Ib) are more potent than ∆8-THC, both in vitro and in vivo. The isomers of (Ic) are approximately equal in potency to ∆8-THC, and (Id) is less potent. Between the epimers is relatively little difference in potency. -(HUFFMAN, J. W.; LAINTON, J. A. H.; BANNER, W. K.; DUNCAN, S. G. JUN.; JORDAN, R. D.; YU, S.; DAI, D.; MARTIN, B. R.; WILEY, J. L.; COMPTON, D. R.; Tetrahedron 53 (1997) 5, 1557-1576; Howard L. Hunter Lab., Clemson Univ., Clemson, SC 29634, USA; EN)