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Structure–Activity Relationships for 10,10-dimethylalkyl-D8-tetrahydrocannabinols - Huffmann, Mill

Structure–Activity Relationships for 10,10-dimethylalkyl-D8-tetrahydrocannabinols - Huffmann, Mill

  1. Micklemouse
    John W. Huffman,a,* John R. A. Miller,a John Liddle,a Shu Yu,a Brian F. Thomas,b
    Jenny L. Wileyc and Billy R. Martinc

    Abstract—A series of 10,10-dimethylalkyl-8-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, 10,10-dimethylethyl-
    8-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 agonists in vivo. 10,10-Dimethylundecyl-8-THC (8, n=9) has
    significant affinity for the receptor (Ki=25.85.8 nM), buthas reduced potency in vivo. The dodecyl analogue (8, n=10) has little
    affinity for the CB1 receptor and is inactive in vivo. A quantitative structure–activity relationship study of the side chain region of
    these compounds is consistent with the concept that for optimum affinity and potency the side chain must be of a length which will
    permit its terminus to loop back in proximity to the phenolic ring of the cannabinoid.
    # 2003 Elsevier Science Ltd. All rights reserved