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2-AG | 870450

2-arachidonoyl glycerol

870450O

Oil

870450O-
5mg
$126.00

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2-Arachidonoylglycerol (2-AG), is an endocannabinoid, an endogenous agonist of the CB1 receptor. 2-AG, unlike anandamide, is present at relatively high levels in the central nervous system; it is the most abundant molecular species of monoacylglycerol found in mouse and rat brain (~5-10 nmol/g tissue). Detection of 2-AG in brain tissue is complicated by the relative ease of its isomerization to 1-AG during standard lipid extraction conditions. Unlike anandamide, formation of 2-AG is calcium-dependent and is mediated by the activities of phospholipase C (PLC) and diacylglycerol lipase (DAGL). 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 hydrolyzed in vitro by monoacylglycerol lipase (MAGL), fatty acid amide hydrolase (FAAH), and the uncharacterized serine hydrolase enzymes ABHD6 and ABHD12. The exact contribution of each of these enzymes to the termination of 2-AG signaling in vivo is unknown, though it is estimated that MAGL is responsible for ~85% of this activity.
Molecular Formula
C23H38O4
Percent Composition
C 72.98%, H 10.12%, O 16.91%
Purity
>98% AG (contains <5% 1-AG)
Stability
3 Months
Storage
-20°C
CAS Number
53847-30-6
CAS Registry Number is a Registered Trademark of the American Chemical Society
Molecular Weight
378.545
Exact Mass
378.277
Synonyms
5Z,8Z,11Z,14Z-eicosatetraenoic acid, 2-glyceryl ester
Packaged in Teflon vials, sealed in foil pouch
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Janssen, F.J. and M. van der Stelt. (2016). Inhibitors of diacylglycerol lipases in neurodegenerative and metabolic disorders. Bioorg Med Chem Lett 26:3831-7. [PubMed]Keimpema, E., A. Alpar, F. Howell, K. Malenczyk, C. Hobbs, Y.L. Hurd, M. Watanabe, K. Sakimura, M. Kano, P. Doherty, and T. Harkany. (2013). Diacylglycerol lipase alpha manipulation reveals developmental roles for intercellular endocannabinoid signaling. Sci Rep 3:2093 [PubMed]Jung, K.M., J.R. Clapper, J. Fu, G. D'Agostino, A. Guijarro, D. Thongkham, A. Avanesian, G. Astarita, N.V. Dipatrizio, A. Frontini, S. Cinti, S. Diano, and D. Piomelli. (2012). 2-arachidonoylglycerol signaling in forebrain regulates systemic energy metabolism. Cell Metab 15:299-310. [PubMed]Long, J.Z., Li, W., Booker, L., Burston, J.J., Kinsey, S.G., Schlosburg, J.E., Pavón, F.J., Serrano, A.M., Selley, D.E., Parsons, L.H., Lichtman, A.H., Cravatt, B.F. Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects. Nat Chem Biol. 5 37-44 (2009). [PubMed]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). [PubMed]Stella, N., Schweitzer, P., Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388 773-778 (1997). [PubMed]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 2794-2801 (1999). [PubMed]Kondo, S., Kondo, H., Nakane, S., et al. 2-Arachidonoylglycerol, an endogenous cannabinoidreceptor 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 429 152-156 (1998). [PubMed]