2-[(3-{2-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)(2H3)methylamino]-1-(4-chlorophenyl)ethan-1-one

• ChemBase ID: 172365
• Molecular Formular: C26H27ClN2O
• Molecular Mass: 418.95838
• Monoisotopic Mass: 418.18119117
• SMILES: C(CN(CC(=O)c1ccc(cc1)Cl)C)CN1c2c(CCc3c1cccc3)cccc2
• Canonical SMILES: CN(CC(=O)c1ccc(cc1)Cl)CCCN1c2ccccc2CCc2c1cccc2
• InChI: InChI=1S/C26H27ClN2O/c1-28(19-26(30)22-13-15-23(27)16-14-22)17-6-18-29-24-9-4-2-7-20(24)11-12-21-8-3-5-10-25(21)29/h2-5,7-10,13-16H,6,11-12,17-19H2,1H3
• InChIKey: SAPNXPWPAUFAJU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3-{2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)(^2H₃)methylamino]-1-(4-chlorophenyl)ethan-1-one
• IUPAC Traditional name: 2-[(3-{2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)(^2H₃)methylamino]-1-(4-chlorophenyl)ethanone
• Synonyms: 1-(4-Chlorophenyl)-2-[[3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)propyl](methyl-d3)amino]ethanone; 4'-Chloro-2-[[3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)propyl-(methyl-d3)-amino]acetophenone; Amplit-d3; Leo 640-d3; Lopramine-d3; Lofepramine-d3

Database IDs

• PubChem SID: 164228275
• PubChem CID: 46782071

CALCULATED PROPERTIES

• Acid pKa: 17.023232
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 5.0470443
• LogD (pH = 7.4): 6.059832
• Log P: 6.1148357
• Molar Refractivity: 125.3121 cm^3
• Polarizability: 47.967773 Å^3
• Polar Surface Area: 23.55 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L469382

Psychotropic drug related to imipramine. Antidepressant.

REFERENCES

• Tulic, J.R., et al.: Acta Pharmacol. Toxicol., 32, 304 (1973)
• Plym Forshell, G., et al.: Xenobiotica, 5, 73 (1973)
• Wright, S., et al.: Arzneim.-Forsch., 26, 1167 (1973)