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Submit ReviewN-Arachidonylglycine
Description: GPR18 agonist; endocannabinoid
Alternative Names: NAGly
Chemical Name: N-(1-oxo-5Z,8Z,11Z,14Z-eicosatetraenyl)glycine
Purity: ≥98% (HPLC)
Biological Activity for N-Arachidonylglycine
N-Arachidonylglycine is a 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 for N-Arachidonylglycine
| M. Wt | 361.52 |
| Formula | C22H35NO3 |
| Storage | Desiccate at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 179113-91-8 |
| PubChem ID | 5283389 |
| InChI Key | YLEARPUNMCCKMP-DOFZRALJSA-N |
| Smiles | O=C(NCC(O)=O)CCC\C=C/C\C=C/C/C=C\C/C=C\CCCCC |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Product Datasheets for N-Arachidonylglycine
References for N-Arachidonylglycine
References are publications that support the biological activity of the product.
Burnstein et al (2000) Oxidative metabolism of anandamide. Prostaglandins Other Lipid Mediat. 61 29 PMID: 10785540
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
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
Sheskin et al (1997) Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J.Med.Chem. 40 659 PMID: 9057852
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
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
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Keywords: N-Arachidonylglycine, N-Arachidonylglycine supplier, endocannabinoids, Suppresses, pain, vivo, Receptors, NAGly, Other, Cannabinoids, Glycine, Transporters, 1445, Tocris Bioscience
Citations for N-Arachidonylglycine
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Currently there are no citations for N-Arachidonylglycine.
Reviews for N-Arachidonylglycine
Average Rating: 5 (Based on 1 Review.)
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Product used to significantly inhibit TNF alpha and IFN gamma production.
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Anonymous on 08/29/2019
Species: Human
Product used to significantly inhibit TNF alpha and IFN gamma production.It shows potential as a therapeutic treatment for chronic inflammation and interactive effects on immune system.
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Cannabinoid Receptor Ligands Scientific Review
Written by Roger Pertwee, this review discusses compounds which affect the activity of the endocannabinoid system, focusing particularly on ligands that are most widely used as experimental tools and denotes compounds available from Tocris.