An internal standard for the quantification of 2-arachidonoyl glycerol
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Alternative(s)
3621622-Arachidonoyl Glycerol-d5
Unlabeled Version(s)
621602-Arachidonoyl Glycerol
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2-Arachidonoyl Glycerol-d8

Item No. 362160

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5Z,8Z,11Z,14Z-eicosatetraenoic-5,6,8,9,11,12,14,15-d8 acid, 2-glyceryl ester
CAS Number
924894-97-3
Synonyms
  • 2-AG-d8
Molecular Formula
C23H30D8O4
Formula Weight
386.6
Purity
≥99% deuterated forms (d1-d8)
Formulation
A 100 µg/ml solution in acetonitrile
Solubility(Learn about Variance in Solubility)
DMSO: 10 mg/mlEthanol: MisciblePBS (7.2): ~150 µg/ml
SMILES
OCC(CO)OC(CCC/C([2H])=C([2H])\C/C([2H])=C([2H])\C/C([2H])=C([2H])\C/C([2H])=C([2H])\CCCCC)=O
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-/i6D,7D,9D,10D,12D,13D,15D,16D
InChi Key
RCRCTBLIHCHWDZ-FBFLGLDDSA-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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Certificates of Analysis & Batch Specific Data

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    25 µg

    $87

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    50 µg

    $165

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    100 µg

    $313

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    500 µg

    $1,304

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    Product Description

    2-Arachidonoyl glycerol-d8 (2-AG-d8) is intended for use as an internal standard for the quantification of 2-AG (Item No. 62160) by GC- or LC-MS. 2-AG is an endogenous agonist of the CB1 receptor.1,2 Unlike anandamide, 2-AG is present at relatively high levels in the central nervous system; it is the most abundant molecular species of monoacylglycerol found in rat brain.1,3 Formation of 2-AG is calcium-dependent and is mediated by the activities of phospholipase C and diacylglycerol 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 receptor-dependent mechanism.4

    WARNING This product is not for human or veterinary use.

    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. The Journal of Biological Chemisty 274(5), 2794-2801 (1999).

    3. 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 Lett. 429(2), 152-156 (1998).

    4. 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).

    Gouveia-Figueira, S., Karlsson, J., Deplano, A., et al. Characterisation of (R)-2-(2-fluorobiphenyl-4-yl)-N-(3-methylpyridin-2-yl)propanamide as a dual fatty acid amide hydrolase: Cyclooxygenase inhibitor. PLoS One 10(9), e0139212 (2015).

    Endsley, M.P., Thill, R., Choudhry, I., et al. Expression and function of fatty acid amide hydrolase in protstate cancer. Int. J. Cancer 123(6), 1318-1326 (2008).

    Rouzer, C.A., and Marnett, L.J. Glycerylprostaglandin synthesis by resident peritoneal macrophages in response to a zymosan stimulus. The Journal of Biological Chemisty 280(29), 26690-26700 (2005).