N-Arachidonylglycine (NA-Gly) is a carboxyl analog of the endocannabinoid anandamide (AEA) and a GPR18 agonist (EC50 = 44.5 nM). Unlike AEA, N-Arachidonylglycine is inactive at both CB1 and CB2 receptors. N-Arachidonylglycine inhibits GLYT2 (IC50 = 5.1 μM). N-Arachidonylglycine is also a potent activator of endometrial cell migration.

Physicochemical Properties

Molecular Formula	C22H35NO3
Molecular Weight	361.52
Exact Mass	361.261
CAS #	179113-91-8
PubChem CID	5283389
Appearance	White to yellow solid powder
Density	1.0±0.1 g/cm3
Boiling Point	560.9±50.0 °C at 760 mmHg
Flash Point	293.0±30.1 °C
Vapour Pressure	0.0±3.3 mmHg at 25°C
Index of Refraction	1.508
LogP	5.88
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	16
Heavy Atom Count	26
Complexity	476
Defined Atom Stereocenter Count	0
SMILES	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCC(=O)O
InChi Key	YLEARPUNMCCKMP-DOFZRALJSA-N
InChi Code	InChI=1S/C22H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21(24)23-20-22(25)26/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-20H2,1H3,(H,23,24)(H,25,26)/b7-6-,10-9-,13-12-,16-15-
Chemical Name	2-[[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]amino]acetic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	GlyT2 5.1 μM (IC50)
ln Vitro	In GPR18-transfected HEK293 cells, N-arachidonylglycine (0.1 nM-100 µM; 5 min) induces MAPK activation[1]. Even at doses up to 100 μm, N-arachidonylglycine exhibits no action at GLYT1 or GAT1[2].
ln Vivo	Anandamide blood concentrations are increased nine times by oral N-arachidonylglycine (10 mg/kg)[3]. The oral administration of N-arachidonylglycine (1.2 mg/kg; once) significantly reduces peritoneal cells by 70%[3].
Cell Assay	Western Blot Analysis[1] Cell Types: HEK293-GPR18 cells Tested Concentrations: 0.1 nM-100 µM Incubation Duration: 5 min Experimental Results: Drove MAPK activation.
Animal Protocol	Animal/Disease Models: Rats[3] Doses: 10 mg/kg Route of Administration: Oral Experimental Results: Inhibition of FAAH, causing a reduction in the hydrolytic cleavage of anandamid. Animal/Disease Models: Mouse (peritonitis model)[3] Doses: 1.2 mg/kg Route of Administration: Oral; once Experimental Results: Resulted in a significant 70% reduction of peritoneal cells.
References	[1]. 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]. 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.
Additional Infomation	N-arachidonoylglycine is biologically active derivative of anandamide It is a N-acylglycine and a fatty amide. It is functionally related to an arachidonic acid. It is a conjugate acid of a N-arachidonoylglycinate. N-arachidonoylglycine has been reported in Homo sapiens with data available.

Solubility Data

Solubility (In Vitro)

DMSO: 100 mg/mL (276.61 mM) Ethanol: 50 mg/mL (138.30 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (6.92 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.92 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (6.92 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		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

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.