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179113-91-8

179113-91-8 structure
179113-91-8 structure
  • Name: N-Arachidonylglycine
  • Chemical Name: N-Arachidonylglycine,N-(1-oxo-5Z,8Z,11Z,14Z-eicosatetraenyl)glycine
  • CAS Number: 179113-91-8
  • Molecular Formula: C22H35NO3
  • Molecular Weight: 361.518
  • Catalog: Signaling Pathways Membrane Transporter/Ion Channel GlyT
  • Create Date: 2018-02-11 08:00:00
  • Modify Date: 2025-08-20 23:53:12
  • 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].
Name N-Arachidonylglycine,N-(1-oxo-5Z,8Z,11Z,14Z-eicosatetraenyl)glycine
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
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].
Related Catalog
Target

GlyT2:5.1 μM (IC50)

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.
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.
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.
Density 1.0±0.1 g/cm3
Boiling Point 560.9±50.0 °C at 760 mmHg
Molecular Formula C22H35NO3
Molecular Weight 361.518
Flash Point 293.0±30.1 °C
Exact Mass 361.261688
PSA 66.40000
LogP 5.88
Vapour Pressure 0.0±3.3 mmHg at 25°C
Index of Refraction 1.508
Safety Phrases S22-S24/25
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