1-Arachidonoyl-d5-rac-glycerol

1-Arachidonyl-d₅-rac-glycerol (1-AG-d₅) is intended for use as an internal standard for the quantification of 1-AG by GC- or LC-MS. The glyceryl esters of arachidonic acid have been proposed as endogenous cannabinoid ligands.¹ 2-AG is 10 to 100 times more potent than 1-AG in ligand binding affinity and agonist activity at the CB₁ receptor,² and is thus considered to be the natural ligand. However, 2-AG is chemically unstable and undergoes rapid isomerization to 1-AG (synonymous with 1(3)-AG) both in vitro and in vivo. 1-AG is a frequent contaminant in synthetic 2-AG preparations, and can markedly reduce their cannabinergic potency. 1-AG is a weak CB₁ receptor agonist and may have other pharmacologic properties.

1.Sugiura, T., Kodaka, T., Kondo, S., et al.2-Arachidonoylglycerol, a putative endogenous cannabinoid receptor ligand, induces rapid, transient elevation of intracellular free Ca2+ in neuroblastoma X glioma hybrid NG108-15 cellsBiochemical and Biophysical Research Communications22958-64(1996) 2.Sugiura, T., Kodaka, T., Kondo, S., et al.Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor• Structural requirements for triggering a Ca2+ transient in NG108-15 cellsJ. Biochem.122(4)890-895(1997)