N-arachidonoylglycine

Base Information

• Chemical Name: N-arachidonoylglycine
• CAS No.: 179113-91-8
• Molecular Formula: C22H35NO3
• Molecular Weight: 361.52
• NSC Number: 746569
• UNII: 5PB56SQA6E
• DSSTox Substance ID: DTXSID5045124
• Nikkaji Number: J1.404.839A
• Wikipedia: N-Arachidonylglycine
• Wikidata: Q18378715
• Pharos Ligand ID: TTGWLUPKZJZF
• Metabolomics Workbench ID: 4504
• ChEMBL ID: CHEMBL161343
• Mol file: 179113-91-8.mol

Synonyms:EMA-1 20:4;N-arachidonoyl glycine;N-arachidonylglycine;NAGly amino acid

Chemical Property of N-arachidonoylglycine

Chemical Property:

• Boiling Point: 560.9 °C at 760 mmHg
• PKA: 3.58±0.10(Predicted)
• Flash Point: 293 °C
• PSA: 66.40000
• Density: 0.985 g/cm³
• LogP: 5.72380
• Storage Temp.: −20°C
• Sensitive.: Air Sensitive
• Solubility.: DMSO: >5 mg/mL, soluble
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 16
• Exact Mass: 361.26169398
• Heavy Atom Count: 26
• Complexity: 476

Purity/Quality:

98%Min ^*data from raw suppliers

N-Arachidonylglycine ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCC(=O)O
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCC(=O)O
• Description: 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 signaling pathways.
• Uses: 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 signaling pathways.[Cayman Chemical] An endogenous anandamide-like compound; also acts as a T-type Ca2+ channel blocker and an endogenous GLYT2 inhibitor.

Technology Process of N-arachidonoylglycine

There total 3 articles about N-arachidonoylglycine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) + glycine (56-40-6,18875-39-3,25718-94-9) → N-arachidonoylglycine (179113-91-8)

Guidance literature:

all cis 5,8,11,14-eicosatetraenoic acid; With 1,1'-carbonyldiimidazole; In dichloromethane; at 20 ℃; for 0.5h;

glycine; In dichloromethane; for 12h;

DOI:10.1055/s-0037-1611939

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → N-arachidonoylglycine (179113-91-8)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride, DMF / CH₂Cl₂ / 1 h

2: 2 N aq. KOH / CH₂Cl₂ / 1 h

With potassium hydroxide; oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane;

DOI:10.1021/jm960752x

Reference yield:

arachidonoyl chloride (57303-04-5) + glycine (56-40-6,18875-39-3,25718-94-9) → N-arachidonoylglycine (179113-91-8)

Guidance literature:

With potassium hydroxide; In dichloromethane; for 1h; Yield given;

DOI:10.1021/jm960752x

upstream raw materials:

arachidonoyl chloride

glycine

all cis 5,8,11,14-eicosatetraenoic acid

Refernces

• 1、 Sheskin, Tzviel,Hanu?, Lumir,Slager, Joram,Vogel, Zvi,Mechoulam, Raphael. "Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor". . p. 659 - 667. Retrieved 2007/10/03.