title: The cannabinoid acids, analogs and endogenous counterparts.
abstract: The cannabinoid acids are a structurally heterogeneous group of compounds some of which are endogenous molecules and others that are metabolites of phytocannabinoids. The prototypic endogenous substance is N-arachidonoyl glycine (NAgly) that is closely related in structure to the cannabinoid agonist anandamide. The most studied phytocannabinoid is Δ(9)-THC-11-oic acid, the principal metabolite of Δ(9)-THC. Both types of acids have in common several biological actions such as low affinity for CB1 anti-inflammatory activity and analgesic properties. This suggests that there may be similarities in their mechanism of action, a point that is discussed in this review. Also presented are reports on analogs of the acids that provide opportunities for the development of novel therapeutic agents, such as ajulemic acid.
authors.affiliation: Department of Biochemistry and Molecular Pharmacology, The University of Massachusetts Medical School, Worcester, MA 01605, USA. Electronic address: sumner.burstein@umassmed.edu.
authors.forename: Sumner H
authors.initials: SH
authors.lastname: Burstein
mesh_terms: D000700:Analgesics / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D000818:Animals; D002186:Cannabinoids / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D013759:Dronabinol / Q000031:analogs & derivatives / Q000494:pharmacology; D063388:Endocannabinoids / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D006801:Humans; D015394:Molecular Structure
chemical_list: D000700:Analgesics; D002186:Cannabinoids; D063388:Endocannabinoids; D013759:Dronabinol; C471849:lenabasum
keywords: Ajulemic acid; Cannabinoid; Lipoamino acid; Lipoxin; NAgly; Prostaglandin; Δ(9)-THC-11-oic acid
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