Introduction：Basic information about CAS 179113-91-8|N-Arachidonylglycine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | N-Arachidonylglycine |
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| CAS Number | 179113-91-8 | Molecular Weight | 361.518 |
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| Density | 1.0±0.1 g/cm3 | Boiling Point | 560.9±50.0 °C at 760 mmHg |
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| Molecular Formula | C22H35NO3 | Melting Point | / |
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| MSDS | / | Flash Point | 293.0±30.1 °C |
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Names
| Name | N-Arachidonylglycine,N-(1-oxo-5Z,8Z,11Z,14Z-eicosatetraenyl)glycine |
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| Synonym | More Synonyms |
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N-Arachidonylglycine BiologicalActivity
| Description | N-Arachidonylglycine (NA-Gly), a carboxylic analog of the endocannabinoid anandamide (AEA), is a GPR18 agonist (EC50 = 44.5 nM). Unlike AEA, N-Arachidonylglycine has no activity at either CB1 or CB2 receptors. N-Arachidonylglycine inhibits GLYT2 (IC50 = 5.1 μM). N-Arachidonylglycine also is an effective activator of endometrial cell migration[1][2]. |
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| Related Catalog | Research Areas >>Inflammation/ImmunologySignaling Pathways >>Membrane Transporter/Ion Channel >>GlyTSignaling Pathways >>Neuronal Signaling >>GlyT |
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| Target | GlyT2:5.1 μM (IC50) |
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| In Vitro | N-Arachidonylglycine (0.1 nM-100 µM; 5 min) drives MAPK activation in GPR18-transfected HEK293 cells[1]. N-Arachidonylglycine shows no activity at GLYT1 or GAT1 at concentrations up to 100 μm[2]. Western Blot Analysis[1] Cell Line: HEK293-GPR18 cells Concentration: 0.1 nM-100 µM Incubation Time: 5 min Result: Drove MAPK activation. |
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| In Vivo | N-Arachidonylglycine (10 mg/kg; oral) increases blood concentrations of anandamide 9-fold[3]. N-Arachidonylglycine (1.2 mg/kg; oral; once) results in a significant 70% reduction of peritoneal cells[3]. Animal Model: Rats[3] Dosage: 10 mg/kg Administration: Oral Result: Inhibition of FAAH, causing a reduction in the hydrolytic cleavage of anandamid. Animal Model: Mouse (peritonitis model)[3] Dosage: 1.2 mg/kg Administration: Oral; once Result: Resulted in a significant 70% reduction of peritoneal cells. |
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| References | [1]. McHugh D, et al. Δ(9) -Tetrahydrocannabinol and N-arachidonyl glycine are full agonists at GPR18 receptors and induce migration in human endometrial HEC-1B cells. Br J Pharmacol. 2012;165(8):2414-2424. [2]. Edington AR, et al. Extracellular loops 2 and 4 of GLYT2 are required for N-arachidonylglycine inhibition of glycine transport. J Biol Chem. 2009;284(52):36424-36430. [3]. Burstein SH. N-Acyl Amino Acids (Elmiric Acids): Endogenous Signaling Molecules with Therapeutic Potential. Mol Pharmacol. 2018;93(3):228-238. |
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Chemical & Physical Properties
| Density | 1.0±0.1 g/cm3 |
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| Boiling Point | 560.9±50.0 °C at 760 mmHg |
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| Molecular Formula | C22H35NO3 |
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| Molecular Weight | 361.518 |
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| Flash Point | 293.0±30.1 °C |
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| Exact Mass | 361.261688 |
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| PSA | 66.40000 |
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| LogP | 5.88 |
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| Vapour Pressure | 0.0±3.3 mmHg at 25°C |
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| Index of Refraction | 1.508 |
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| InChIKey | YLEARPUNMCCKMP-DOFZRALJSA-N |
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| SMILES | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCC(=O)O |
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Safety Information
Synonyms
| N-[(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoyl]glycine |
| NAGLY |
| N-Arachidonoylglycine |
| N-[(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoyl]glycine |
| Glycine, N-[(5Z,8Z,11Z,14Z)-1-oxo-5,8,11,14-eicosatetraen-1-yl]- |
| arachidonoyl glycine |
| N-ARACHIDONYL GLYCINE |
