2-Arachidonoyl Glycerol (CAS 53847-30-6) | Cayman Chemical
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2-Arachidonoyl Glycerol

Item № 62160
CAS № 53847-30-6
Purity ≥95% (as a 9:1 mixture of the 2-AG and 1-AG)
product image
                (CAS 53847-30-6)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $22.00 0.00
     5 mg $88.00 0.00
     10 mg $132.00 0.00
     25 mg $248.00 0.00

Pricing updated 2018-11-16. Prices are subject to change without notice.

Description
Synonyms
  • 2-AG

2-Arachidonoyl glycerol (2-AG) is an endogenous agonist of the cannabinoid (CB) receptors CB1 and CB2 (Kis = 25.3-472 and 145-1,400 nM, respectively).1,2,3 Unlike arachidonoyl ethanolamide (AEA; Item No. 90050), 2-AG is present at relatively high levels in the central nervous system and is the most abundant molecular species of monoacylglycerol (MAG) found in rat brain.1,4 Formation of 2-AG is calcium-dependent and is mediated by the activities of phospholipase C (PLC) and diacylglycerol (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 (FAAH), with MAG lipase likely being the principle metabolizing enzyme in vivo.5

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Technical Information
Formal Name
5Z,8Z,11Z,14Z-eicosatetraenoic acid, 2-glyceryl ester
CAS Number
53847-30-6
Synonyms
  • 2-AG
Molecular Formula
C23H38O4
Formula Weight
378.6
Purity
≥95% (as a 9:1 mixture of the 2-AG and 1-AG)
Formulation
A solution in acetonitrile
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-
InChI Key
RCRCTBLIHCHWDZ-DOFZRALJSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
Stability
≥ 6 months
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Additional Information

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References & Product Citations
Product Description References

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. Pertwee, R.G. Pharmacology of cannabinoid receptor ligands Curr. Med. Chem. 6(8), 635-664 (1999).

4. 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 Letters 429(2), 152-156 (1998).

5. Dinh, T.P., Carpenter, D., Leslie, F.M., et al. Brain monoglyceride lipase participating in endocannabinoid inactivation Proceedings of the National Academy of Sciences of the United States of America 99(16), 10819-10824 (2002).

Product Citations

Archambault, A.-S., Turcotte, C., Martin, C., et al. Comparison of eight 15-lipoxygenase (LO) inhibitors on the biosynthesis of 15-LO metabolites by human neutrophils and eosinophils PLOS One 13(8), (2018).

Kantae, V., Ogino, S., Noga, M., et al. Quantitative profiling of endocannabinoids and related N-acylethanolamines in human CSF using nano LC-MS/MS J. Lipid. Res. 58(3), 615-624 (2017).

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