title: Heteroadamantyl cannabinoids.
abstract: The aliphatic side chain plays a pivotal role in determining the cannabinergic potency of tricyclic classical cannabinoids. We have synthesized a series of analogues in which the C3 position is substituted either directly or through a one-carbon atom linker with an adamantylamine or with an oxa- or an oxazaadamantane. The oxaadamantane pharmacophore in analogue 16 showed the best binding profile for both receptors.
authors.affiliation: Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii 96822, USA.
authors.forename: Darryl D
authors.initials: DD
authors.lastname: Dixon
authors.forename: Divakaramenon
authors.initials: D
authors.lastname: Sethumadhavan
authors.forename: Tore
authors.initials: T
authors.lastname: Benneche
authors.forename: April R
authors.initials: AR
authors.lastname: Banaag
authors.forename: Marcus A
authors.initials: MA
authors.lastname: Tius
authors.forename: Ganesh A
authors.initials: GA
authors.lastname: Thakur
authors.forename: Anna
authors.initials: A
authors.lastname: Bowman
authors.forename: Jodianne T
authors.initials: JT
authors.lastname: Wood
authors.forename: Alexandros
authors.initials: A
authors.lastname: Makriyannis
mesh_terms: D000218:Adamantane / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D001921:Brain / Q000378:metabolism; D002186:Cannabinoids / Q000138:chemical synthesis* / Q000494:pharmacology; D002460:Cell Line; D006801:Humans; D066298:In Vitro Techniques; D051379:Mice; D008958:Models, Molecular; D011869:Radioligand Assay; D051381:Rats; D043884:Receptor, Cannabinoid, CB1 / Q000378:metabolism*; D043885:Receptor, Cannabinoid, CB2 / Q000378:metabolism*; D013329:Structure-Activity Relationship
chemical_list: D002186:Cannabinoids; D043884:Receptor, Cannabinoid, CB1; D043885:Receptor, Cannabinoid, CB2; D000218:Adamantane