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

• ChemBase ID: 165739
• Molecular Formular: C19H20ClFN2O
• Molecular Mass: 346.8263032
• Monoisotopic Mass: 346.12481917
• SMILES: c1c(ccc2c1COC2(c1ccc(cc1)F)CCCNC)C#N.Cl
• Canonical SMILES: CNCCCC1(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
• InChIKey: DYIZNULSIBGJPJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-fluorophenyl)-1-[3-(methylamino)propyl]-1,3-dihydro-2-benzofuran-5-carbonitrile hydrochloride
• IUPAC Traditional name: demethylcitalopram hydrochloride
• Synonyms: 1-(4-Fluorophenyl)-1-(3-methylamino-propyl)-1,3-dihydro-isobenzofuran-5-carbonitrile Hydrochloride; 1-(3-Methylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile; rac Desmethyl Citalopram Hydrochloride

Database IDs

• CAS Number: 97743-99-2
• PubChem SID: 162259872
• PubChem CID: 46780600

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: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 60-65°C

Safety Information

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

DETAILS

Toronto Research Chemicals - D230846

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

REFERENCES

• Gnerre, C., et al.: J. Pharm. Pharmacol., 53, 1125 (2001)
• Hagg, S., et al.: Br. J. Clin. Pharmacol., 51, 169 ( 2001), von Moltke, L., et al.: Drug Metab. Dispos., 29, 1102 (2001)
• Reis, M., et al.: Ther. Drug Monit., 27, 469 (2001)