N-Arachidonylglycine

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].

Product Specifications

CAS Number

[179113-91-8]

Product Name Alternative

NA-Gly

UNSPSC

12352211

Hazard Statement

H315, H319, H336, H351

Target

Endogenous Metabolite; GlyT

Type

Reference compound

Related Pathways

Membrane Transporter/Ion Channel; Metabolic Enzyme/Protease; Neuronal Signaling

Applications

COVID-19-immunoregulation

Field of Research

Inflammation/Immunology

Assay Protocol

https://www.medchemexpress.com/n-arachidonylglycine.html

Concentration

138.30 mM * 2 mL in Ethanol

Purity

99.65

Solubility

DMSO : 100 mg/mL (ultrasonic; warming; heat to 60°C) |Ethanol : 50 mg/mL (ultrasonic)

Smiles

O=C(O)CNC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O

Molecular Formula

C22H35NO3

Molecular Weight

361.52

Precautions

H315, H319, H336, H351

References & Citations

[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.