(1S)-1-(4-fluorophenyl)-1-[3-(methylamino)propyl]-1,3-dihydro-2-benzofuran-5-carbonitrile hydrochloride

• ChemBase ID: 166422
• Molecular Formular: C19H20ClFN2O
• Molecular Mass: 346.8263032
• Monoisotopic Mass: 346.12481917
• SMILES: c1c(ccc2c1CO[C@]2(c1ccc(cc1)F)CCCNC)C#N.Cl
• Canonical SMILES: CNCCC[C@]1(OCc2c1ccc(c2)C#N)c1ccc(cc1)F.Cl
• InChI: InChI=1S/C19H19FN2O.ClH/c1-22-10-2-9-19(16-4-6-17(20)7-5-16)18-8-3-14(12-21)11-15(18)13-23-19;/h3-8,11,22H,2,9-10,13H2,1H3;1H/t19-;/m0./s1
• InChIKey: DYIZNULSIBGJPJ-FYZYNONXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-1-(4-fluorophenyl)-1-[3-(methylamino)propyl]-1,3-dihydro-2-benzofuran-5-carbonitrile hydrochloride
• IUPAC Traditional name: (1S)-1-(4-fluorophenyl)-1-[3-(methylamino)propyl]-3H-2-benzofuran-5-carbonitrile hydrochloride
• Synonyms: 1S)-1-(4-Fluorophenyl)-1,3-dihydro-1-[3-(methylamino)propyl]-5-isobenzo-furancarbonitrile Hydrochloride; (S)-1-(3-Methylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile Hydrochloride; (S)-(+)-N-Demethylcitalopram Hydrochloride; S-Desmethyl Citalopram Hydrochloride

Database IDs

• PubChem SID: 162260555
• PubChem CID: 46781157

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.1461039
• LogD (pH = 7.4): 0.49438983
• Log P: 3.3812563
• Molar Refractivity: 88.7255 cm^3
• Polarizability: 33.919804 Å^3
• Polar Surface Area: 45.05 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 80-82°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D291571

A metabolite of Citalopram, an inhibitor of serotonin (5-HT) uptake. Used as an antidepressant.

REFERENCES

• Carlsson, B., et al.: Ther. Drug Monit., 23, 658 (1999)
• Kugelberg, F., et al.: Br. J. Pharmacol., 132, 1683 (1999)
• Olesen, O., et al.: Pharmacology, 59, 298 (1999)
• Zheng, Z., et al.: Ther. Drug Monit., 22, 219 (1999)