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. 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. Formation of 2-AG is calcium-dependent and is mediated by the activities of PLC and DAG lipase. 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-AG is metabolized in vitro by MAG lipase and fatty acid amide hydrolase, with MAG lipase likely being the principle metabolizing enzyme in vivo. Formal Name: 5Z,8Z,11Z,14Z-eicosatetraenoic acid, 2-glycerol-1,1,2,3,3-d5 ester. Synonyms: 2-AG-d5. Molecular Formula: C23H33D5O4. Formula Weight: 383.6. Purity: >99% deuterated forms (d1-d5). Formulation: A solution in acetonitrile. Solubility: DMSO: 10 mg/ml, Ethanol: Miscible, PBS (7.2): ~150 µg/ml. SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO)CO. InChi Code: InChI=1S/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3/b7-6-,10-9-,13-12-,16-15-/i20D2,21D2,22D. InChi Key: RCRCTBLIHCHWDZ-BGRPFJIQSA-N. Side Chain Carbon Sum: 20:4.