2-[(3-{2-azatricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl}propyl)(methyl)amino]-1-(4-chlorophenyl)ethan-1-one hydrochloride

• ChemBase ID: 153212
• Molecular Formular: C26H28Cl2N2O
• Molecular Mass: 455.41932
• Monoisotopic Mass: 454.15786889
• SMILES: CN(CCCN1c2ccccc2CCc2c1cccc2)CC(=O)c1ccc(cc1)Cl.Cl
• Canonical SMILES: CN(CC(=O)c1ccc(cc1)Cl)CCCN1c2ccccc2CCc2c1cccc2.Cl
• InChI: InChI=1S/C26H27ClN2O.ClH/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;1H
• InChIKey: ZWZIQPOLMDPIQM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 hydrochloride
• IUPAC Traditional name: lofepramine hydrochloride
• Synonyms: N-(4-Chlorobenzoylmethyl)-3-(10,11-dihydro-5h-dibenz[b,f]azepin-5-yl)-n-methylpropylamine hydrochloride; Lofepramine hydrochloride

Database IDs

• CAS Number: 26786-32-3
• EC Number: 248-002-2
• MDL Number: MFCD00941486
• PubChem SID: 24724528; 162247351
• PubChem CID: 33611

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: DMSO: ~24 mg/mL; H2O: insoluble
• Apperance: off-white solid

Safety Information

• RTECS: AM6485000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22-37-53
• Safety Statements: 22-24/25-26-28-36/37/39-38
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H335-H413
• GHS Precautionary statements: P261
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C26H28Cl2N2O

DETAILS

Sigma Aldrich - L8792

Biochem/physiol Actions
Lofepramine is an antidepressant; serotonin and norepinephrine re-uptake inhibitor (SNRI).