An endogenous CB receptor ligand
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Isomer(s)
621602-Arachidonoyl Glycerol
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1-Arachidonoyl Glycerol

Item No. 62150

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5Z,8Z,11Z,14Z-eicosatetraenoic acid, 1-glyceryl ester
CAS Number
35474-99-8
Synonyms
  • 1-AG
Molecular Formula
C23H38O4
Formula Weight
378.6
Purity
≥95% (as a 9:1 mixture of the 1-AG and 2-AG)
Formulation
A 10 mg/ml solution in acetonitrile
Solubility(Learn about Variance in Solubility)
Ethanol: MiscibleEthanol:PBS (1:2): 3 mg/ml
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCC(O)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)27-21-22(25)20-24/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
DCPCOKIYJYGMDN-DOFZRALJSA-N
Side Chain Carbon Sum
20:4
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    1 mg

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    25 mg

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    Product Description

    The glyceryl esters of arachidonic acid have been proposed as endogenous cannabinoid ligands.1 2-AG is 10 to 100 times more potent than 1-AG in ligand binding affinity and agonist activity at the CB1 receptor, and is thus considered to be the natural ligand.2 However, 2-AG is chemically unstable and undergoes rapid isomerization to 1-AG (synonymous with 1(3)-AG) both in vitro and in vivo. 1-AG is a frequent contaminant in synthetic 2-AG preparations, and can markedly reduce their cannabinergic potency. 1-AG is a weak CB1 receptor agonist and may have other pharmacologic properties.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sugiura, T., Kodaka, T., Kondo, S., et al. 2-Arachidonoylglycerol, a putative endogenous cannabinoid receptor ligand, induces rapid, transient elevation of intracellular free Ca2+ in neuroblastoma X glioma hybrid NG108-15 cells. Biochem. Biophys. Res. Commun. 229(1), 58-64 (1996).

    2. Sugiura, T., Kodaka, T., Kondo, S., et al. Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells. J. Biochem. 122(4), 890-895 (1997).

    Product Citations

    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).