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Arachidonoyl glycine-d8 (NAGly-d8) contains eight deuterium atoms at the 5, 6, 8, 9, 11, 12, 14, and 15 positions. It is intended for use as an internal standard for the quantification of NAGly by GC- or LC-mass spectrometry. NAGly has been isolated from cell cultures treated with arachidonoyl ethanolamide (AEA),1 from extracts of mammalian brain,2,3 and has also been synthesized as an analog of AEA for structure/activity testing.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,4 these effects are probably mediated via other signalling pathways.
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1
Burstein, S.H., Rossetti, R.G., Yagen, B., et al. Oxidative metabolism of anandamide. Prostaglandins and Other Lipid Mediators 61 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 (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. J Biol Chem 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 40 659-667 (1997).
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