N-Arachidonylglycine-d₈  (Synonyms: NA-Gly-d₈)

N-Arachidonylglycine-d8 is a deuterated labeled N-Arachidonylglycine^[1]. 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^[2][3].

Stable heavy isotopes of hydrogen, carbon, and other elements have been incorporated into drug molecules, largely as tracers for quantitation during the drug development process. Deuteration has gained attention because of its potential to affect the pharmacokinetic and metabolic profiles of drugs^[1].
N-Arachidonylglycine (0.1 nM-100 μM; 5 min) drives MAPK activation in GPR18-transfected HEK293 cells^[2].
N-Arachidonylglycine shows no activity at GLYT1 or GAT1 at concentrations up to 100 μm^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

N-Arachidonylglycine (10 mg/kg; oral) increases blood concentrations of anandamide 9-fold^[4].
N-Arachidonylglycine (1.2 mg/kg; oral; once) results in a significant 70% reduction of peritoneal cells^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

369.57

C₂₂H₂₇D₈NO₃

1159908-44-7

179113-91-8

Liquid

Colorless to light yellow

OC(CNC(CCC/C([2H])=C([2H])\C/C([2H])=C([2H])\C/C([2H])=C([2H])\C/C([2H])=C([2H])\CCCCC)=O)=O

Room temperature in continental US; may vary elsewhere.

Solution, -20°C, 2 years

• [1]. Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019 Feb;53(2):211-216.  [Content Brief]

  [2]. 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.  [Content Brief]

  [3]. 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.  [Content Brief]

  [4]. Burstein SH. N-Acyl Amino Acids (Elmiric Acids): Endogenous Signaling Molecules with Therapeutic Potential. Mol Pharmacol. 2018;93(3):228-238.  [Content Brief]