2-Arachidonoyl Glycerol-d5

2-Arachidonoyl Glycerol-d₅

Cayman Chemical Item Number 362162

2-AG-d₅

Description

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 potentiation. Nature 388 773-778 (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 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 429 152-156 (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).

Synonyms

2-AG-d5

Formal Name

5Z,8Z,11Z,14Z-eicosatetraenoic acid, 2-glycerol-1,1,2,3,3-d5 ester

Molecular Formula

C₂₃H₃₃D₅O₄

Formula Weight

383.6

Formulation

A solution in acetonitrile

Purity

≥99% deuterated forms (d1-d5)

Stability

6 months

Storage

-80°C

Shipping

Dry ice in continental US; may vary elsewhere

SMILES

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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO)CO

Background Reading

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 429 152-156 (1998).

Stella, N., Schweitzer, P., and Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388 773-778 (1997).

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).

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2-Arachidonoyl Glycerol-d₅