Structure–activity relationships for 1′, 1′-dimethylalkyl-Δ 8-tetrahydrocannabinols

…, J Liddle, S Yu, BF Thomas, JL Wiley, BR Martin

Index: Huffman, John W.; Miller, John R. A.; Liddle, John; Yu, Shu; Thomas, Brian F.; Wiley, Jenny L.; Martin, Billy R. Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 7 p. 1397 - 1410

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Citation Number: 34

Abstract

A series of 1′, 1′-dimethylalkyl-Δ8-tetrahydrocannabinol analogues with C-3 side chains of 2–12 carbon atoms has been synthesized and their in vitro and in vivo pharmacology has been evaluated. The lowest member of the series, 1′, 1′-dimethylethyl-Δ8-THC (8, n= 0) has good affinity for the CB1 receptor, but is inactive in vivo. The dimethylpropyl (8, n= 1) through dimethyldecyl (8, n= 8) all have high affinity for the CB1 receptor and are full ...