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

• ChemBase ID: 128105
• Molecular Formular: C26H27ClN2O
• Molecular Mass: 418.95838
• Monoisotopic Mass: 418.18119117
• SMILES: Clc1ccc(cc1)C(=O)CN(C)CCCN1c2ccccc2CCc2c1cccc2
• 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)(methyl)amino]-1-(4-chlorophenyl)ethan-1-one; 2-[(3-{2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl}propyl)(methyl)amino]-1-(4-chlorophenyl)ethan-1-one
• IUPAC Traditional name: lofepramine
• Synonyms: 1-(4-Chlorophenyl)-2-[[3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)propyl]methylamino]ethanone; 4'-Chloro-2-[[3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)propyl-methylamino]acetophenone; Amplit; Leo 640; Lopramine; Lofepramine

Database IDs

• CAS Number: 23047-25-8
• PubChem SID: 162222419
• PubChem CID: 3947
• CHEBI ID: 47782
• ATC CODE: N06AA07
• CHEMBL: 87708
• Chemspider ID: 3810
• KEGG ID: D08140
• Unique Ingredient Identifier: OCA4JT7PAW
• Wikipedia Title: Lofepramine

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

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Light Yellow Solid
• Melting Point: 103-105°C

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 4-6 hours (lofepramine - prodrug); 21-23 hours (desipramine - active metabolite)
• Legal Status: Rx-only

DETAILS

Toronto Research Chemicals - L469380

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)