2-methyl-3-(naphthalene-1-carbonyl)-1-propyl-1H-indole

• ChemBase ID: 155206
• Molecular Formular: C23H21NO
• Molecular Mass: 327.41894
• Monoisotopic Mass: 327.1623143
• SMILES: CCCn1c(c(c2c1cccc2)C(=O)c1cccc2c1cccc2)C
• Canonical SMILES: CCCn1c(C)c(c2c1cccc2)C(=O)c1cccc2c1cccc2
• InChI: InChI=1S/C23H21NO/c1-3-15-24-16(2)22(20-12-6-7-14-21(20)24)23(25)19-13-8-10-17-9-4-5-11-18(17)19/h4-14H,3,15H2,1-2H3
• InChIKey: LJSBBBWQTLXQEN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methyl-3-(naphthalene-1-carbonyl)-1-propyl-1H-indole
• IUPAC Traditional name: 2-methyl-3-(naphthalene-1-carbonyl)-1-propylindole
• Synonyms: (2-Methyl-1-propyl-1H-indol-3-yl)-1-naphthalenylmethanone; JWH-015; JWH 015; JWH-015

Database IDs

• CAS Number: 155471-08-2
• MDL Number: MFCD02094630
• PubChem SID: 24278502; 162249344
• PubChem CID: 4273754

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 5.8234053
• LogD (pH = 7.4): 5.8234053
• Log P: 5.8234053
• Molar Refractivity: 103.4892 cm^3
• Polarizability: 42.138294 Å^3
• Polar Surface Area: 22.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL (with heating)
• Apperance: off-white powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... CNR2(1269)rat ... Cnr1(25248)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C23H21NO

DETAILS

Sigma Aldrich - J4252

Biochem/physiol Actions
JWH-015 is a selective CB2 cannabinoid receptor agonist.

Toronto Research Chemicals - J211350

A cannabimimetic indole derivative that acts as a CB2 receptor agonist with weak CB2 activity. It has been shown to possess immunomodulatory effects and may be useful in the treatment of pain and inflammation.

REFERENCES

• Aung, M.M. et al.: Drug Alc. Depend., 60, 133 (2000)
• Ghosh, S. et al.: Mol. Immunol., 43, 2169 (2000)
• Ehrhart, J. et al.: J. Neuroinflam., 2, 29 (2000)
• Romero-Sandoval, A. et al.: Anethesiol., 106, 787 (2000)