N-(2-chloroethyl)icosa-5,8,11,14-tetraenamide

• ChemBase ID: 125920
• Molecular Formular: C22H36ClNO
• Molecular Mass: 365.98034
• Monoisotopic Mass: 365.24854246
• SMILES: ClCCNC(=O)CCC/C=C/C/C=C/C/C=C/C/C=C/CCCCC
• Canonical SMILES: CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)NCCCl
• InChI: InChI=1S/C22H36ClNO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)24-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,24,25)
• InChIKey: SCJNCDSAIRBRIA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-chloroethyl)icosa-5,8,11,14-tetraenamide
• IUPAC Traditional name: N-(2-chloroethyl)icosa-5,8,11,14-tetraenamide
• Synonyms: Arachidonyl-2′-chloroethylamide hydrate; Arachidonyl-2'-chloroethylamide; ACEA; Arachidonyl-2'-chloroethylamide

Database IDs

• CAS Number: 220556-69-4; 220556-69-4(anhydrous)
• MDL Number: MFCD02683581
• PubChem SID: 24891489; 162220264
• PubChem CID: 5353377; 5311006
• CHEMBL: 151167
• Chemspider ID: 4470547
• Wikipedia Title: Arachidonyl-2'-chloroethylamide

CALCULATED PROPERTIES

• Acid pKa: 14.996904
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 6.6683936
• LogD (pH = 7.4): 6.668394
• Log P: 6.668394
• Molar Refractivity: 116.0162 cm^3
• Polarizability: 43.32837 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; H2O: insoluble; soluble in ethanol, chloroform, THF and DMSO
• Apperance: colorless to light yellow oil

Safety Information

• Storage Condition: desiccated
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: mouse ... Cnr1(12801), Cnr2(12802)rat ... Cnr1(25248)

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C22H36ClNO · xH2O

DETAILS

Sigma Aldrich - A9719

Biochem/physiol Actions
Potent and selective neuronal CB1 cannabinoid receptor agonist.
Caution
Photosensitive; store under argon or nitrogen.