Catalog Number: 1445
Alternate Names: 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.
Background References
  1. Oxidative metabolism of anandamide.
    Burnstein et al.
    Prostaglandins Other Lipid Mediat., 2000;61:29
  2. Extracellular loops 2 and 4 of GLYT2 are required for N-arachidonylglycine inhibition of glycine transport.
    Edington et al.
    J.Biol.Chem., 2009;284:36424
  3. Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain.
    Huang et al.
    J.Biol.Chem., 2001;276:42639
  4. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor.
    Sheskin et al.
    J.Med.Chem., 1997;40:659
  5. Identification of N-arachidonylglycine as the endogenous ligand for orphan G-protein-coupled receptor GPR18.
    Kohno et al.
    Biochem Biophys Res Commun., 2006;347:827
  6. Δ9-Tetrahydrocannabinol and N-arachidonyl glycine are full agonists at GPR18 receptors and induce migration in human endometrial HEC-1B cells
    McHugh et al.
    Br.J.Pharmacol., 2012;2414:165

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