N-Arachidonylglycine

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Cat.No. 1445 - N-Arachidonylglycine | C22H35NO3 | CAS No. 179113-91-8
Description: GPR18 agonist; endocannabinoid
Alternative Names: NAGly
Chemical Name: N-(1-oxo-5Z,8Z,11Z,14Z-eicosatetraenyl)glycine
Purity: ≥98% (HPLC)
Datasheet
Citations
Literature

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
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.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
ethanol 36.15 100

Preparing Stock Solutions

The following data is based on the product molecular weight 361.52. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.77 mL 13.83 mL 27.66 mL
5 mM 0.55 mL 2.77 mL 5.53 mL
10 mM 0.28 mL 1.38 mL 2.77 mL
50 mM 0.06 mL 0.28 mL 0.55 mL

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Product Datasheets

Safety Datasheet

References

References are publications that support the products' biological activity.

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, supplier, endocannabinoids, Suppresses, pain, vivo, Receptors, NAGly, Other, Cannabinoids, Tocris Bioscience

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