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870450 | 2-AG

2-arachidonoyl glycerol

2-AG

Oil

Size SKU Packaging Price
5mg 870450O-5mg 870450O-5mg $177.65
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Info

2-AG

2-arachidonoyl glycerol

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.

Note: This product is supplied in a PTFE vial and should not be stored in glass.

Data
Hygroscopic
No
Light Sensitive
Yes
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 Temperature
-80°C
CAS Number
53847-30-6
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula 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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References

Kasatkina LA, Heinemann A, Hudz YA, Thomas D, Sturm EM. Stearoylethanolamide interferes with retrograde endocannabinoid signalling and supports the blood-brain barrier integrity under acute systemic inflammation. Biochem Pharmacol. 2019 Dec 25;174:113783. doi: 10.1016/j.bcp.2019.113783. [Epub ahead of print]. PMID: 31881191.

 PubMed ID: 31881191

Janssen FJ, van der Stelt M. Inhibitors of diacylglycerol lipases in neurodegenerative and metabolic disorders. Bioorg Med Chem Lett. 2016 Aug 15;26(16):3831-7. doi: 10.1016/j.bmcl.2016.06.076. Epub 2016 Jun 27. PMID: 27394666.

 PubMed ID: 27394666

Keimpema E, Alpár A, Howell F, Malenczyk K, Hobbs C, Hurd YL, Watanabe M, Sakimura K, Kano M, Doherty P, Harkany T. Diacylglycerol lipase α manipulation reveals developmental roles for intercellular endocannabinoid signaling. Sci Rep. 2013;3:2093. doi: 10.1038/srep02093. PMID: 23806960; PMCID: PMC3695556.

 PubMed ID: 23806960

Jung KM, Clapper JR, Fu J, D'Agostino G, Guijarro A, Thongkham D, Avanesian A, Astarita G, DiPatrizio NV, Frontini A, Cinti S, Diano S, Piomelli D. 2-arachidonoylglycerol signaling in forebrain regulates systemic energy metabolism. Cell Metab. 2012 Mar 7;15(3):299-310. doi: 10.1016/j.cmet.2012.01.021. PMID: 22405068; PMCID: PMC3729112.

 PubMed ID: 22405068

Long JZ, Li W, Booker L, Burston JJ, Kinsey SG, Schlosburg JE, Pavón FJ, Serrano AM, Selley DE, Parsons LH, Lichtman AH, Cravatt BF. Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects. Nat Chem Biol. 2009 Jan;5(1):37-44. doi: 10.1038/nchembio.129. Epub 2008 Nov 23. PMID: 19029917; PMCID: PMC2605181.

 PubMed ID: 19029917

Dinh TP, Carpenter D, Leslie FM, Freund TF, Katona I, Sensi SL, Kathuria S, Piomelli D. Brain monoglyceride lipase participating in endocannabinoid inactivation. Proc Natl Acad Sci U S A. 2002 Aug 6;99(16):10819-24. doi: 10.1073/pnas.152334899. Epub 2002 Jul 22. Erratum in: Proc Natl Acad Sci U S A 2002 Oct 15;99(21):13961. PMID: 12136125; PMCID: PMC125056.

 PubMed ID: 12136125

Stella N, Schweitzer P, Piomelli D. A second endogenous cannabinoid that modulates long-term potentiation. Nature. 1997 Aug 21;388(6644):773-8. doi: 10.1038/42015. PMID: 9285589.

 PubMed ID: 9285589

Sugiura T, Kodaka T, Nakane S, Miyashita T, Kondo S, Suhara Y, Takayama H, Waku K, Seki C, Baba N, Ishima Y. 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. 1999 Jan 29;274(5):2794-801. doi: 10.1074/jbc.274.5.2794. PMID: 9915812.

 PubMed ID: 9915812

Kondo S, Kondo H, Nakane S, Kodaka T, Tokumura A, Waku K, Sugiura T. 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. 1998 Jun 12;429(2):152-6. doi: 10.1016/s0014-5793(98)00581-x. PMID: 9650580.

 PubMed ID: 9650580
Certificates of Analysis

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