title: The cannabinoid acids: nonpsychoactive derivatives with therapeutic potential.
abstract: The discovery of carboxylic acid metabolites of the cannabinoids (CBs) dates back more than three decades. Their lack of psychotropic activity was noted early on, and this resulted in a total absence of further research on their possible role in the actions of the CBs. More recent studies have revealed that the acids possess both analgesic and anti-inflammatory properties and may contribute to the actions of the parent drug. A synthetic analog showed similar actions at considerably lower doses. In this review, a brief survey of the extensive literature on metabolism of delta 9-tetrahydrocannabinol to the acids is presented, while more emphasis is given to the recent findings on the biological actions of this class of CBs. A possible mechanism involving effects on eicosanoids for some of these actions is also suggested. Finally, an analogy with a putative metabolite of anandamide, an endogenous CB, is discussed.
authors.affiliation: Department of Biochemistry and Molecular Biology, University of Massachusetts Medical School, Worcester 01655-0103, USA.
authors.forename: S H
authors.initials: SH
authors.lastname: Burstein
mesh_terms: D000700:Analgesics / Q000627:therapeutic use*; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000627:therapeutic use*; D001095:Arachidonic Acids / Q000627:therapeutic use*; D002186:Cannabinoids / Q000378:metabolism / Q000627:therapeutic use*; D063388:Endocannabinoids; D006801:Humans; D053284:Polyunsaturated Alkamides; D013329:Structure-Activity Relationship
chemical_list: D000700:Analgesics; D000893:Anti-Inflammatory Agents; D001095:Arachidonic Acids; D002186:Cannabinoids; D063388:Endocannabinoids; D053284:Polyunsaturated Alkamides; C078814:anandamide