Arachidonoyl Glycine

Cayman Chemical Item Number 90051

NAGly; N-Arachidonyl Glycine (CAS 179113-91-8)

Arachidonoyl Glycine (CAS 179113-91-8)

Description

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 signaling pathways.

1 Burstein, S.H., Rossetti, R.G., Yagen, B., et al. Oxidative metabolism of anandamide. Prostaglandins Other Lipid Mediat 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 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. 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).

Synonyms

NAGly
N-Arachidonyl Glycine

Formal Name

N-[1-oxo-5Z,8Z,11Z,14Z-eicosatetraenyl]-glycine

CAS Number

179113-91-8

Molecular Formula

C₂₂H₃₅NO₃

Formula Weight

361.5

Formulation

A solution in ethanol

Purity

>98%

Stability

2 years

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCC

Background Reading

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

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).

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).

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).

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Arachidonoyl Glycine is available in the following screening library:

Bio-active Lipid I Screening Library (96-Well)

Size

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