Arachidonyl-2-chloroethylamide

Base Information

• Chemical Name: Arachidonyl-2-chloroethylamide
• CAS No.: 220556-69-4
• Molecular Formula: C₂₂H₃₆ClNO
• Molecular Weight: 365.987
• DSSTox Substance ID: DTXSID60274346
• Nikkaji Number: J1.087.037B
• Wikipedia: Arachidonyl-2%27-chloroethylamide,Arachidonyl-2'-chloroethylamide
• Wikidata: Q4783527
• Pharos Ligand ID: 675F1XG1KU6U
• ChEMBL ID: CHEMBL151167
• Mol file: 220556-69-4.mol

Synonyms:ACEA cpd;arachidonyl-2'-chloroethylamide;arachidonyl-2-chloroethylamide;N-(2-chloroethyl)-5,8,11,14-eicosatetraenamide

Chemical Property of Arachidonyl-2-chloroethylamide

Chemical Property:

• Appearance/Colour: Pale yellow Oil
• Boiling Point: 517.9 °C at 760 mmHg
• Flash Point: 267 °C
• PSA: 29.10000
• Density: 0.954 g/cm³
• LogP: 6.87800
• Storage Temp.: −20°C
• Sensitive.: Air Sensitive
• Solubility.: DMSO: soluble
• Water Solubility.: DMSO: soluble
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 16
• Exact Mass: 365.2485425
• Heavy Atom Count: 25
• Complexity: 410

Purity/Quality:

99% ^*data from raw suppliers

Arachidonyl-2-chloroethylamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCCl
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCCl
• Description: Arachidonoyl 2-chloroethylamide (ACEA) is a potent and selective cannabinoid (CB) receptor 1 agonist with Ki values of 1.4 and >2,000 nM for CB1 and CB2 receptors, respectively. In whole animal experiments, ACEA induces hypothermia in mice with the same efficacy as arachidonoyl ethanolamide (AEA; ), in spite of its higher affinity for the CB1 receptor. These data have been interpreted to indicate that ACEA may be a substrate for fatty acid amide hydrolase (FAAH), and thus only transiently available in whole animal experiments.
• Uses: A synthetic agonist of the cannabinoid receptor 1 (CB1R). ACEA is considered to be a selective cannabinoid agonist as it binds primarily to the CB1R and has low affinity to the cannabinoid receptor 2 (CB2R).

Technology Process of Arachidonyl-2-chloroethylamide

There total 3 articles about Arachidonyl-2-chloroethylamide 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: 90.0%

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) + 2-chloroethanamine hydrochloride (870-24-6) → arachidonoyl-2-chloroethylamide (220556-69-4)

Guidance literature:

all cis 5,8,11,14-eicosatetraenoic acid; With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 ℃; for 1h;

2-chloroethanamine hydrochloride; With pyridine; In dichloromethane; at 0 - 20 ℃; for 0.5h;

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → arachidonoyl-2-chloroethylamide (220556-69-4)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride / dimethylformamide; benzene / 1 h / 0 °C

2: pyridine / CH₂Cl₂; dimethylformamide / 0.5 h / Ambient temperature

With pyridine; oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm970257g

Reference yield:

2-chloroethanamine hydrochloride (870-24-6) + arachidonoyl chloride (57303-04-5) → arachidonoyl-2-chloroethylamide (220556-69-4)

Guidance literature:

With pyridine; In dichloromethane; N,N-dimethyl-formamide; for 0.5h; Yield given; Ambient temperature;

DOI:10.1021/jm970257g

upstream raw materials:

2-chloroethanamine hydrochloride

arachidonoyl chloride

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

Refernces

• 1、 Hillard, Cecilia J.,Manna, Sukumar,Greenberg, Marcie J.,Dicamelli, Ralph,Ross, Ruth A.,Stevenson, Lesley A.,Murphy, Vicki,Pertwee, Roger G.,Campbell, William B.. "Synthesis and characterization of potent and selective agonists of the neuronal cannabinoid receptor (CB1)". . p. 1427 - 1433. Retrieved 2007/10/03.