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870818 | N-arachidonoylglycine

N-arachidonoylglycine

N-arachidonoylglycine

Methylene Chloride

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10mg 870818M-10mg 870818M-10mg $113.10
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N-arachidonoylglycine

N-arachidonoylglycine

Arachidonoyl glycine (N-arachidonyl glycine; NAGly) has been isolated from cell cultures treated with arachidonoyl ethanolamide (AEA; anandamide),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 CoA. 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.
1 Burstein, S.H., Rossetti, R.G., Yagen, B., Zurier, R.B. (2000) Oxidative metabolism of anandamide. Prostaglandins and Other Lipid Mediators 61:29-41.
2 Huang, S.M., et al. (2001) Identification and characterization of an endogenous anandamide-like compound: N-arachidonylglycine (NAGly). ICRS 2001 Symposium on the Cannabinoids.
3 Huang, S.M., Bisogno, T., Petros, T.J., Chang, S.Y., Zavitsanos, P.A., Zipkin, R.E., Sivakumar, R., Coop, A., Maeda, D.Y., De Petrocellis, L., Burstein, S., Di Marzo, V., Walker, J.M. (2001) Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain. J Biol Chem 276:42639-42644.
4 Sheskin, T., Hanus, L., Slager, J., Vogel, Z., Mechoulam, R. (1997) Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J Med Chem 40:659-667.
Data
Hygroscopic
No
Light Sensitive
No
Molecular Formula
C22H35NO3
Percent Composition
C 73.09%, H 9.76%, N 3.87%, O 13.28%
Purity
>99%
Stability
3 Months
Storage Temperature
-20°C
CAS Number
179113-91-8
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
361.518
Exact Mass
361.262
Synonyms
NAGly
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References

Burstein SH, Rossetti RG, Yagen B, Zurier RB. Oxidative metabolism of anandamide. Prostaglandins Other Lipid Mediat. 2000 Apr;61(1-2):29-41. doi: 10.1016/s0090-6980(00)00053-8. PMID: 10785540.

 PubMed ID: 10785540

Huang SM, Bisogno T, Petros TJ, Chang SY, Zavitsanos PA, Zipkin RE, Sivakumar R, Coop A, Maeda DY, De Petrocellis L, Burstein S, Di Marzo V, Walker JM. Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain. J Biol Chem. 2001 Nov 16;276(46):42639-44. doi: 10.1074/jbc.M107351200. Epub 2001 Aug 22. PMID: 11518719.

 PubMed ID: 11518719

Sheskin T, Hanus L, Slager J, Vogel Z, Mechoulam R. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J Med Chem. 1997 Feb 28;40(5):659-67. doi: 10.1021/jm960752x. PMID: 9057852.

 PubMed ID: 9057852
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