2-Arachidonoyl Glycerol-d5

2-Arachidonoyl glycerol-d₅ (2-AG-d₅) contains five deuterium atoms at the 1, 1, 2, 3, and 3 positions of the glycerol moiety. It is intended for use as an internal standard for the quantification of 2-AG by GC- or LC-mass spectrometry. 2-Arachidonoyl glycerol (2-AG) is an endogenous agonist of the CB₁ receptor.^1,2 Unlike anandamide, 2-AG is present at relatively high levels in the central nervous system; it is the most abundant molecular species of monoacylglycerol found in rat brain.^1,3 Formation of 2-AG is calcium-dependent and is mediated by the activities of PLC and DAG lipase.¹ 2-AG acts as a full agonist at the CB₁ receptor. At a concentration of 0.3 nM, 2-AG induces a rapid, transient increase in intracellular free calcium in NG108-15 neuroblastoma X glioma cells through a CB₁ receptor-dependent mechanism.² 2-AG is metabolized in vitro by MAG lipase and fatty acid amide hydrolase, with MAG lipase likely being the principle metabolizing enzyme in vivo.⁴

1.Stella, N., Schweitzer, P., and Piomelli, D.A second endogenous cannabinoid that modulates long-term potentiationNature388(6644)773-778(1997) 2.Sugiura, T., Kodaka, T., Nakane, S., et al.Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compoundsJ. Biol. Chem.274(5)2794-2801(1999) 3.Kondo, S., Kondo, H., Nakane, S., et al.2-Arachidonoylglycerol, an endogenous cannabinoid receptor agonist: Identification as one of the major species of monoacylglycerols in various rat tissues, and evidence for its generation through Ca2+-dependent and -independent mechanismsFEBS Letters429(2)152-156(1998) 4.Dinh, T.P., Carpenter, D., Leslie, F.M., et al.Brain monoglyceride lipase participating in endocannabinoid inactivationProceedings of the National Academy of Sciences of the United States of America99(16)10819-10824(2002)