Enantioselective synthesis and pharmacology of 11-hydroxy-(1'S,2'R)-dimethylheptyl-delta 8-THC.
An enantioselective synthesis of the (1'S,2'R)-dimethylheptyl cannabinoid side chain has been developed and employed in the synthesis of 11-hydroxy-(1'S,2'R)-dimethylheptyl-delta 8-THC (3). Pharmacology, in vivo and in vitro, indicate (3) to be one of the most potent traditional cannabinoids known.
Liddle
J
J
Department of Chemistry, Clemson University, SC 29634-1905, USA.
Huffman
J W
JW
Wiley
J L
JL
Martin
B R
BR
D000818:Animals; D001667:Binding, Competitive; D001921:Brain / Q000378:metabolism; D002186:Cannabinoids / Q000493:pharmacokinetics; D002462:Cell Membrane / Q000378:metabolism; D003511:Cyclohexanols / Q000493:pharmacokinetics; D013759:Dronabinol / Q000031:analogs & derivatives* / Q000737:chemistry; D007202:Indicators and Reagents; D007700:Kinetics; D051379:Mice; D015394:Molecular Structure; D043882:Receptors, Cannabinoid; D011955:Receptors, Drug / Q000187:drug effects / Q000378:metabolism*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D002186:Cannabinoids; D003511:Cyclohexanols; D007202:Indicators and Reagents; D043882:Receptors, Cannabinoid; D011955:Receptors, Drug; D013759:Dronabinol; C054649:3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol