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N-Arachidonylglycine

Names

[ CAS No. ]:
179113-91-8

[ Name ]:
N-Arachidonylglycine

[Synonym ]:
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

Biological Activity

[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]:

Research Areas >> Inflammation/Immunology
Signaling Pathways >> Membrane Transporter/Ion Channel >> GlyT
Signaling Pathways >> Neuronal Signaling >> GlyT

[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.

Chemical & Physical Properties

[ 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 Information

[ Safety Phrases ]:
S22-S24/25

Related Compounds