[CAS NO. 179113-91-8] N-Arachidonylglycine
PRODUCTS SPECIFICATIONS [179113-91-8]
DESCRIPTION [179113-91-8]
Overview
| MDL | - |
|---|---|
| Molecular Weight | 361.52 |
| Molecular Formula | C22H35NO3 |
| SMILES | O=C(O)CNC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O |
Summary
N-Arachidonylglycine (NA-Gly), a carboxylic analog of the endocannabinoid anandamide (AEA), is a GPR18 agonist ( EC 50 = 44.5 nM). Unlike AEA, N-Arachidonylglycine has no activity at either CB1 or CB2 receptors. N-Arachidonylglycine inhibits GLYT2 ( IC 50 = 5.1 μM). N-Arachidonylglycine also is an effective activator of endometrial cell migration [1] [2] .
IC50 & Target
|
GlyT2 5.1 μM (IC 50 ) |
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]
.
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
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]
.
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
| 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. |
Appearance
Oil
Shipping
Room temperature in continental US; may vary elsewhere.
Storage
-20°C, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
Solvent & Solubility
DMSO : 50 mg/mL ( 138.30 mM ; Need ultrasonic)
Stock Solutions
| Concentration Solvent Mass | 1 mg | 5 mg | 10 mg |
|---|
| 1 mM | 2.7661 mL | 13.8305 mL | 27.6610 mL |
| 5 mM | 0.5532 mL | 2.7661 mL | 5.5322 mL |
| 10 mM | 0.2766 mL | 1.3830 mL | 2.7661 mL |
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.
Synonyms