2-Arachidonoylglycerol

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 561428

CAS#: 53847-30-6

Description: 2-Arachidonoylglycerol is an endocannabinoid, an endogenous agonist of the CB1 receptor. At a concentration of 0.3nM, 2-Arachidonoylglycerol induces a rapid, transient increase in intracellular free calcium in NG108-15 neuroblastoma X glioma cells through a CB1 receptor-dependent mechanism.


Price and Availability

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2-Arachidonoylglycerol is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 561428
Name: 2-Arachidonoylglycerol
CAS#: 53847-30-6
Chemical Formula: C23H38O4
Exact Mass: 378.277
Molecular Weight: 378.55
Elemental Analysis: C, 72.98; H, 10.12; O, 16.91


Synonym: 2-Arachidonoylglycerol; 2-Arachidonoyl Glycerol; 2 Arachidonoylglycerol; 2Arachidonoylglycerol; 2-AG; 2AG; 2 AG;

IUPAC/Chemical Name: 1,3-Dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

InChi Key: RCRCTBLIHCHWDZ-DOFZRALJSA-N

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-

SMILES Code: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(OC(CO)CO)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Poursharifi P, Madiraju SRM, Prentki M. Monoacylglycerol signalling and ABHD6 in health and disease. Diabetes Obes Metab. 2017 Sep;19 Suppl 1:76-89. doi: 10.1111/dom.13008. Review. PubMed PMID: 28880480.

2: Dyall SC. Interplay Between n-3 and n-6 Long-Chain Polyunsaturated Fatty Acids and the Endocannabinoid System in Brain Protection and Repair. Lipids. 2017 Sep 5. doi: 10.1007/s11745-017-4292-8. [Epub ahead of print] Review. PubMed PMID: 28875399.

3: Stern CAJ, de Carvalho CR, Bertoglio LJ, Takahashi RN. Effects of cannabinoid drugs on aversive or rewarding drug-associated memory extinction and reconsolidation. Neuroscience. 2017 Jul 17. pii: S0306-4522(17)30488-8. doi: 10.1016/j.neuroscience.2017.07.018. [Epub ahead of print] Review. PubMed PMID: 28729064.

4: Deng H, van der Stelt M. Chemical tools to modulate 2-arachidonoylglycerol biosynthesis. Biotechnol Appl Biochem. 2017 Jun 6. doi: 10.1002/bab.1568. [Epub ahead of print] Review. PubMed PMID: 28589628.

5: Lau BK, Cota D, Cristino L, Borgland SL. Endocannabinoid modulation of homeostatic and non-homeostatic feeding circuits. Neuropharmacology. 2017 Sep 15;124:38-51. doi: 10.1016/j.neuropharm.2017.05.033. Epub 2017 Jun 1. Review. PubMed PMID: 28579186.

6: Korf HW. Signaling pathways to and from the hypophysial pars tuberalis, an important center for the control of seasonal rhythms. Gen Comp Endocrinol. 2017 May 13. pii: S0016-6480(17)30232-0. doi: 10.1016/j.ygcen.2017.05.011. [Epub ahead of print] Review. PubMed PMID: 28511899.

7: Lu Y, Anderson HD. Cannabinoid signaling in health and disease. Can J Physiol Pharmacol. 2017 Apr;95(4):311-327. doi: 10.1139/cjpp-2016-0346. Epub 2017 Mar 6. Review. PubMed PMID: 28263083.

8: Yuan D, Wu Z, Wang Y. Evolution of the diacylglycerol lipases. Prog Lipid Res. 2016 Oct;64:85-97. doi: 10.1016/j.plipres.2016.08.004. Epub 2016 Aug 26. Review. PubMed PMID: 27568643.

9: Karhson DS, Hardan AY, Parker KJ. Endocannabinoid signaling in social functioning: an RDoC perspective. Transl Psychiatry. 2016 Sep 27;6(9):e905. doi: 10.1038/tp.2016.169. Review. PubMed PMID: 27676446; PubMed Central PMCID: PMC5048207.

10: Biernacki M, Skrzydlewska E. Metabolism of endocannabinoids. Postepy Hig Med Dosw (Online). 2016 Aug 11;70(0):830-43. Review. PubMed PMID: 27516570.

11: Huang WJ, Chen WW, Zhang X. Endocannabinoid system: Role in depression, reward and pain control (Review). Mol Med Rep. 2016 Oct;14(4):2899-903. doi: 10.3892/mmr.2016.5585. Epub 2016 Aug 1. Review. PubMed PMID: 27484193; PubMed Central PMCID: PMC5042796.

12: 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. Review. PubMed PMID: 27394666.

13: Russo EB. Clinical Endocannabinoid Deficiency Reconsidered: Current Research Supports the Theory in Migraine, Fibromyalgia, Irritable Bowel, and Other Treatment-Resistant Syndromes. Cannabis Cannabinoid Res. 2016 Jul 1;1(1):154-165. doi: 10.1089/can.2016.0009. eCollection 2016. Review. PubMed PMID: 28861491; PubMed Central PMCID: PMC5576607.

14: Sharkey KA, Wiley JW. The Role of the Endocannabinoid System in the Brain-Gut Axis. Gastroenterology. 2016 Aug;151(2):252-66. doi: 10.1053/j.gastro.2016.04.015. Epub 2016 Apr 29. Review. PubMed PMID: 27133395; PubMed Central PMCID: PMC4961581.

15: Rock EM, Sticht MA, Limebeer CL, Parker LA. Cannabinoid Regulation of Acute and Anticipatory Nausea. Cannabis Cannabinoid Res. 2016 Apr 1;1(1):113-121. doi: 10.1089/can.2016.0006. eCollection 2016. Review. PubMed PMID: 28861486; PubMed Central PMCID: PMC5576606.

16: Iannotti FA, Di Marzo V, Petrosino S. Endocannabinoids and endocannabinoid-related mediators: Targets, metabolism and role in neurological disorders. Prog Lipid Res. 2016 Apr;62:107-28. doi: 10.1016/j.plipres.2016.02.002. Epub 2016 Mar 7. Review. PubMed PMID: 26965148.

17: Tegeder I. Endocannabinoids as Guardians of Metastasis. Int J Mol Sci. 2016 Feb 10;17(2):230. doi: 10.3390/ijms17020230. Review. PubMed PMID: 26875980; PubMed Central PMCID: PMC4783962.

18: Keereetaweep J, Chapman KD. Lipidomic Analysis of Endocannabinoid Signaling: Targeted Metabolite Identification and Quantification. Neural Plast. 2016;2016:2426398. doi: 10.1155/2016/2426398. Epub 2015 Dec 29. Review. PubMed PMID: 26839710; PubMed Central PMCID: PMC4709765.

19: Lu HC, Mackie K. An Introduction to the Endogenous Cannabinoid System. Biol Psychiatry. 2016 Apr 1;79(7):516-25. doi: 10.1016/j.biopsych.2015.07.028. Epub 2015 Oct 30. Review. PubMed PMID: 26698193; PubMed Central PMCID: PMC4789136.

20: Sticht MA, Rock EM, Limebeer CL, Parker LA. Endocannabinoid Mechanisms Influencing Nausea. Int Rev Neurobiol. 2015;125:127-62. doi: 10.1016/bs.irn.2015.09.001. Epub 2015 Nov 6. Review. PubMed PMID: 26638766.