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
Appearance
A solution in acetonitrile
Purity
≥95% (as a 9:1 mixture of the 2-AG and 1-AG)
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).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
378.55
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
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.
