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 (Item No. 62150) 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.

WARNING This product is not for human or veterinary use.

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 cells. Biochem. Biophys. Res. Commun. 229(1), 58-64 (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 cells. J. Biochem. 122(4), 890-895 (1997).

Archambault, A.-S., Brassard, J., Bernatchez, É., et al. Human and mouse eosinophils differ in their ability to biosynthesize eicosanoids, docosanoids, the endocannabinoid 2-arachidonoyl-glycerol and its congeners. Cells 11(1), 141 (2022).