2522598-88-3

2-Arachidonoyl glycerol-d₅ (2-AG-d₅) is intended for use as an internal standard for the quantification of 2-AG by GC- or LC-MS. 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 potentiation Nature 388(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 compounds J. 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 mechanisms FEBS Lett. 429(2),152-156(1998).
4. Dinh, T.P., Carpenter, D., Leslie, F.M., et al. Brain monoglyceride lipase participating in endocannabinoid inactivation Proc. Natl. Acad. Sci. USA 99(16),10819-10824(2002).