An internal standard for the quantification of arachidonoyl glycine
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Unlabeled Version(s)
90051Arachidonoyl Glycine
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Arachidonoyl Glycine-d8

Item No. 10007531

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(5Z,8Z,11Z,14Z)-1-oxo-5,8,11,14-eicosatetraen-1-yl-5,6,8,9,11,12,14,15-d8]-glycine
CAS Number
1159908-44-7
Synonyms
  • NAGly-d8
  • N-Arachidonyl Glycine-d8
Molecular Formula
C22H27D8NO3
Formula Weight
369.6
Purity
≥99% deuterated forms (d1-d8)
Formulation (Request formulation change)
A 1 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 15 mg/mlEthanol: 25 mg/mlPBS (pH 7.2): 2 mg/ml
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCC(=O)O
InChi Code
InChI=1S/C22H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21(24)23-20-22(25)26/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-20H2,1H3,(H,23,24)(H,25,26)/b7-6-,10-9-,13-12-,16-15-/i6D,7D,9D,10D,12D,13D,15D,16D
InChi Key
YLEARPUNMCCKMP-FBFLGLDDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 µg

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    Product Description

    Arachidonoyl glycine-d8 (NAGly-d8) is intended for use as an internal standard for the quantification of NAGly by GC- or LC-MS. NAGly has been isolated from cell cultures treated with arachidonoyl ethanolamide (AEA), from extracts of mammalian brain, and has also been synthesized as an analog of AEA for structure/activity testing.1,2,3,4 NAGly may be produced endogenously via oxidation of AEA, or by transacylation of arachidonoyl coenzyme A. NAGly is reported to have analgesic activities in whole animal experiments.1,2,3 Since it seems to be a very poor ligand for the CB1 receptor, these effects are probably mediated via other signalling pathways.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Burstein, S.H., Rossetti, R.G., Yagen, B., et al. Oxidative metabolism of anandamide. Prostaglandins Other Lipid Mediat. 61(1-2), 29-41 (2000).

    2. Huang, S.M., Bisogno, T., Petros, T.J., et al. Identification and characterization of an endogenous anandamide-like compound: N-Arachidonylglycine (NAGly). ICRS 2001 Symposium on the Cannabinoids 78 (2001).

    3. Huang, S.M., Bisogno, T., Petros, T.J., et al. Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain. The Journal of Biological Chemisty 276(46), 42639-42644 (2001).

    4. Sheskin, T., Hanus, L., Slager, J., et al. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J. Med. Chem. 40(5), 659-667 (1997).