Variation of the alkyl side chain in delta 8-THC.
The synthesis of (2'RS)-2'-methyl-, (3'RS)-, (3'S)-3'-methyl-, and 4'-methyl-delta 8-THC has been carried out, and the pharmacology of all four compounds has been investigated. All four compounds showed typical cannabinoid activity both in vitro and in vivo. The 2'-methyl compound is somewhat more active than delta 8-THC, while the 4'-methyl isomer is less active. The 3'-methyl-delta 8-THC has approximately the same activity as the parent cannabinoid.
Huffman
J W
JW
Department of Chemistry, Clemson University, South Carolina 29634-1905, USA.
Lainton
J A
JA
Dai
D
D
Jordan
R D
RD
Duncan
S G
SG
D000700:Analgesics / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D001667:Binding, Competitive; D002375:Catalepsy / Q000139:chemically induced; D003511:Cyclohexanols / Q000378:metabolism; D013759:Dronabinol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D007035:Hypothermia / Q000139:chemically induced; D051379:Mice; D009043:Motor Activity / Q000187:drug effects; D013329:Structure-Activity Relationship
D000700:Analgesics; D003511:Cyclohexanols; C035731:delta-8-tetrahydrocannabinol; D013759:Dronabinol; C054649:3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol