Novel conformationally restricted tetracyclic analogs of delta8-tetrahydrocannabinol.
Novel analogs of (-)-delta8-tetrahydrocannabinol (delta8-THC) in which the conformation of the side chain was restricted by incorporating the first one or two carbons into a six membered ring fused with the aromatic phenolic A ring were synthesized. The affinities of the novel ligands for CB1 and CB2 indicated that the "southbound" chain conformer retained the highest affinity for both receptors.
Khanolkar
A D
AD
Department of Pharmaceutical Sciences, University of Connecticut, Storrs 06269, USA.
Lu
D
D
Fan
P
P
Tian
X
X
Makriyannis
A
A
D000818:Animals; D001921:Brain / Q000378:metabolism; D002462:Cell Membrane / Q000187:drug effects / Q000378:metabolism; D013759:Dronabinol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D051379:Mice; D051381:Rats; D043885:Receptor, Cannabinoid, CB2; D043882:Receptors, Cannabinoid; D011955:Receptors, Drug / Q000187:drug effects / Q000378:metabolism; D013154:Spleen / Q000378:metabolism; D013329:Structure-Activity Relationship
C469526:Cnr2 protein, rat; D043885:Receptor, Cannabinoid, CB2; D043882:Receptors, Cannabinoid; D011955:Receptors, Drug; C035731:delta-8-tetrahydrocannabinol; D013759:Dronabinol