N-arachidonoylglycine | CAS# 179113-91-8 | analgesic

MedKoo Cat#: 412706 | Name: N-arachidonoylglycine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Arachidonoyl glycine (N-arachidonyl glycine; NAGly) has been isolated from cell cultures treated with arachidonoyl ethanolamide (AEA; anandamide), from extracts of mammalian brain, and has also been synthesized as an analog of AEA for structure/activity testing. NAGly may be produced endogenously via oxidation of AEA, or by transacylation of arachidonoyl CoA. NAGly is reported to have analgesic activities in whole animal experiments. Since it seems to be a very poor ligand for the CB1 receptor, these effects are probably mediated via other signalling pathways.

Chemical Structure

N-arachidonoylglycine

CAS#179113-91-8

Theoretical Analysis

MedKoo Cat#: 412706

Name: N-arachidonoylglycine

CAS#: 179113-91-8

Chemical Formula: C22H35NO3

Exact Mass: 361.2617

Molecular Weight: 361.53

Elemental Analysis: C, 73.09; H, 9.76; N, 3.87; O, 13.28

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 295.00	2 Weeks
25mg	USD 610.00	2 Weeks

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Related CAS #

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Synonym

N-arachidonoylglycine; NAGly

IUPAC/Chemical Name

((5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl)glycine

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-

SMILES Code

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

Appearance

Colorless to light yellow oil

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

N-Arachidonylglycine (NA-Gly), a carboxylic analog of the endocannabinoid anandamide (AEA), is a GPR18 agonist (EC50 = 44.5 nM).

In vitro activity:

By screening using a lipid library, N-arachidonylglycine (NAGly) induced an increase in intracellular Ca(2+) concentration in GPR18-transfected cells, which was significantly greater than that in mock-transfected cells. NAGly also inhibited forskolin-induced cAMP production in a pertussis toxin-sensitive manner in the GPR18-transfected CHO cells. Reference: Biochem Biophys Res Commun. 2006 Sep 1;347(3):827-32. https://pubmed.ncbi.nlm.nih.gov/16844083/

In vivo activity:

The effects of NAGly (N-Arachidonylglycine) on endothelial electrical signalling were studied in combination with vascular reactivity. NAGly (0.3-30 μM) suppressed NCX currents in a URB597- and guanosine 5'-O-(2-thiodiphosphate) (GDPβS)-insensitive manner, [Ca²⁺]i elevation evoked by Na⁺ removal and the hyperpolarization to histamine. In rat aorta, NAGly opposed the endothelial hyperpolarization and relaxation response to ACh. Reference: Br J Pharmacol. 2013 Jun;169(4):933-48. https://pubmed.ncbi.nlm.nih.gov/23517055/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	55.32
	DMSO	32.5	89.90
	Ethanol	50.0	138.30
	Methyl Acetate	10.0	27.66
	PBS (pH 7.2)	2.0	5.53

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 361.53 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. McHugh D, Page J, Dunn E, Bradshaw HB. 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 Apr;165(8):2414-24. doi: 10.1111/j.1476-5381.2011.01497.x. PMID: 21595653; PMCID: PMC3423258. 2. Kohno M, Hasegawa H, Inoue A, Muraoka M, Miyazaki T, Oka K, Yasukawa M. Identification of N-arachidonylglycine as the endogenous ligand for orphan G-protein-coupled receptor GPR18. Biochem Biophys Res Commun. 2006 Sep 1;347(3):827-32. doi: 10.1016/j.bbrc.2006.06.175. Epub 2006 Jul 10. PMID: 16844083. 3. Bondarenko AI, Drachuk K, Panasiuk O, Sagach V, Deak AT, Malli R, Graier WF. N-Arachidonoyl glycine suppresses Na⁺/Ca²⁺ exchanger-mediated Ca²⁺ entry into endothelial cells and activates BK(Ca) channels independently of GPCRs. Br J Pharmacol. 2013 Jun;169(4):933-48. doi: 10.1111/bph.12180. PMID: 23517055; PMCID: PMC3687672. 4. Parmar N, Ho WS. N-arachidonoyl glycine, an endogenous lipid that acts as a vasorelaxant via nitric oxide and large conductance calcium-activated potassium channels. Br J Pharmacol. 2010 Jun;160(3):594-603. doi: 10.1111/j.1476-5381.2009.00622.x. Epub 2010 Feb 5. PMID: 20136843; PMCID: PMC2931560.

In vitro protocol:

In vivo protocol:

1. Bondarenko AI, Drachuk K, Panasiuk O, Sagach V, Deak AT, Malli R, Graier WF. N-Arachidonoyl glycine suppresses Na⁺/Ca²⁺ exchanger-mediated Ca²⁺ entry into endothelial cells and activates BK(Ca) channels independently of GPCRs. Br J Pharmacol. 2013 Jun;169(4):933-48. doi: 10.1111/bph.12180. PMID: 23517055; PMCID: PMC3687672. 2. Parmar N, Ho WS. N-arachidonoyl glycine, an endogenous lipid that acts as a vasorelaxant via nitric oxide and large conductance calcium-activated potassium channels. Br J Pharmacol. 2010 Jun;160(3):594-603. doi: 10.1111/j.1476-5381.2009.00622.x. Epub 2010 Feb 5. PMID: 20136843; PMCID: PMC2931560.

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