1-{3-[bis(2H3)methylamino]propyl}-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile; oxalic acid

• ChemBase ID: 164799
• Molecular Formular: C22H23FN2O5
• Molecular Mass: 414.4268232
• Monoisotopic Mass: 414.15910007
• SMILES: c1c(ccc2c1COC2(c1ccc(cc1)F)CCCN(C)C)C#N.C(=O)(O)C(=O)O
• Canonical SMILES: OC(=O)C(=O)O.N#Cc1ccc2c(c1)COC2(CCCN(C)C)c1ccc(cc1)F
• InChI: InChI=1S/C20H21FN2O.C2H2O4/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20;3-1(4)2(5)6/h4-9,12H,3,10-11,14H2,1-2H3;(H,3,4)(H,5,6)
• InChIKey: KTGRHKOEFSJQNS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{3-[bis(^2H₃)methylamino]propyl}-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile; oxalic acid
• IUPAC Traditional name: 1-{3-[bis(^2H₃)methylamino]propyl}-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile; oxalic acid
• Synonyms: 1-[3-(Dimethylamino-d6)propyl]-1-(4-fluorophenyl)-1,3-dizohydro-5-isobenzofurancarbonitrile Oxalate Salt; Citalopram-d6 Oxalate

Database IDs

• PubChem SID: 162258933
• PubChem CID: 71314878

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.3290631
• LogD (pH = 7.4): 1.409549
• Log P: 3.7643042
• Molar Refractivity: 94.0202 cm^3
• Polarizability: 35.7618 Å^3
• Polar Surface Area: 36.26 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C505003

Labelled Citalopram (C505000), an inhibitor of serotonin (5-HT) uptake. Used as an antidepressant.

REFERENCES

• Christensen, A.V., et al.: Eur. J. Pharmacol., 41, 153 (1977)
• Keller, M.B., et al.: J. Clin. Psychiatry, 61, 896 (1977)
• Von Moltke, L.L., et al.: Drug Metab. Dispos., 29, 1102 (1977)