N-Arachidonylglycine

Cat. No. 1445

N-Arachidonylglycine C22H35NO3 [179113-91-8]

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Alternative Name: NAGly

Chemical Name: N-(1-oxo-5Z,8Z,11Z,14Z-eicosatetraenyl)glycine

Biological Activity

GPR18 agonist (EC50 = 44.5 nM). Endogenous anandamide-like compound. Lacks affinity for CB1 receptors (Ki > 10 μM), VR1 receptors (EC50 > 10 μM) and anandamide transporters (IC50 > 50 μM) but causes hot-plate analgesia in mice when given orally, and suppresses tonic inflammatory pain. Also endogenous GlyT2 inhibitor.

Technical Data

M.Wt:
361.52
Formula:
C22H35NO3
Solubility:
Soluble to 100 mM in ethanol
Purity:
>98 %
Storage:
Desiccate at -20°C
CAS No:
179113-91-8

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
All Tocris products are intended for laboratory research use only.

Certificate of Analysis / Product Datasheet / Safety Datasheet

References are publications that support the products' biological activity.

McHugh et al (2012) Δ9-Tetrahydrocannabinol and N-arachidonyl glycine are full agonists at GPR18 receptors and induce migration in human endometrial HEC-1B cells Br.J.Pharmacol. 2414 165. PMID: 21595653.

Edington et al (2009) Extracellular loops 2 and 4 of GLYT2 are required for N-arachidonylglycine inhibition of glycine transport. J.Biol.Chem. 284 36424. PMID: 19875446.

Kohno et al (2006) Identification of N-arachidonylglycine as the endogenous ligand for orphan G-protein-coupled receptor GPR18. Biochem Biophys Res Commun. 347 827. PMID: 16844083.

Huang et al (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. PMID: 11518719.

Burnstein et al (2000) Oxidative metabolism of anandamide. Prostaglandins Other Lipid Mediat. 61 29. PMID: 10785540.

Sheskin et al (1997) Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J.Med.Chem. 40 659. PMID: 9057852.

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Keywords: N-Arachidonylglycine, supplier, endocannabinoids, Suppresses, pain, vivo, Receptors, Tocris Bioscience, Other Cannabinoid Agonist products

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