2-(2-chlorophenyl)-1-(1-pentyl-1H-indol-3-yl)ethan-1-one

• ChemBase ID: 127953
• Molecular Formular: C21H22ClNO
• Molecular Mass: 339.85848
• Monoisotopic Mass: 339.13899201
• SMILES: Clc1ccccc1CC(=O)c1cn(CCCCC)c2ccccc12
• Canonical SMILES: CCCCCn1cc(c2c1cccc2)C(=O)Cc1ccccc1Cl
• InChI: InChI=1S/C21H22ClNO/c1-2-3-8-13-23-15-18(17-10-5-7-12-20(17)23)21(24)14-16-9-4-6-11-19(16)22/h4-7,9-12,15H,2-3,8,13-14H2,1H3
• InChIKey: YDINKDBAZJOSLV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-chlorophenyl)-1-(1-pentyl-1H-indol-3-yl)ethan-1-one
• IUPAC Traditional name: 2-(2-chlorophenyl)-1-(1-pentylindol-3-yl)ethanone
• Synonyms: JWH-203; 2-(2-Chlorophenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone; JWH 203

Database IDs

• CAS Number: 864445-54-5
• PubChem SID: 162222269
• PubChem CID: 44397500
• Wikipedia Title: JWH-203

CALCULATED PROPERTIES

• Acid pKa: 13.033397
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 6.0601835
• LogD (pH = 7.4): 6.0601826
• Log P: 6.0601835
• Molar Refractivity: 100.4453 cm^3
• Polarizability: 39.900997 Å^3
• Polar Surface Area: 22.0 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 101-103°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Legal Status: I-N (Poland)

DETAILS

Toronto Research Chemicals - J211450

A cannabimimetic indole derivative that acts as both a cannabinoid receptor CB1 and CB2 agonist.

REFERENCES

• Huffman J.W. et al.: Bioorg. Med. Chem. Lett., 15, 4110 (2005)
• De Freitas, G.B.L. et al.: Eur. J. Med. Chem., 44, 2482 (2005)
• Tuccinardi, T. et al.: J. Med. Chem., 49, 984 (2005)