(chloromethyl)({3-[(1S)-5-cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]propyl})dimethylazanium chloride

• ChemBase ID: 164438
• Molecular Formular: C21H23Cl2FN2O
• Molecular Mass: 409.3245232
• Monoisotopic Mass: 408.11714695
• SMILES: c1(ccc2c(c1)CO[C@]2(c1ccc(cc1)F)CCC[N+](CCl)(C)C)C#N.[Cl-]
• Canonical SMILES: N#Cc1ccc2c(c1)CO[C@@]2(CCC[N+](CCl)(C)C)c1ccc(cc1)F.[Cl-]
• InChI: InChI=1S/C21H23ClFN2O.ClH/c1-25(2,15-22)11-3-10-21(18-5-7-19(23)8-6-18)20-9-4-16(13-24)12-17(20)14-26-21;/h4-9,12H,3,10-11,14-15H2,1-2H3;1H/q+1;/p-1/t21-;/m0./s1
• InChIKey: NBPWOQRBNRRAJK-BOXHHOBZSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (chloromethyl)({3-[(1S)-5-cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]propyl})dimethylazanium chloride
• IUPAC Traditional name: (chloromethyl)({3-[(1S)-5-cyano-1-(4-fluorophenyl)-3H-2-benzofuran-1-yl]propyl})dimethylazanium chloride
• Synonyms: (1S)-N-(Chloromethyl)-5-cyano-1-(4-fluorophenyl)-1,3-dihydro-N,N-dimethyl- 1-isobenzofuranpropanaminium Chloride; N-Chloromethyl Escitalopram Chloride; N-Chloromethyl (S)-Citalopram Chloride

Database IDs

• PubChem SID: 162258573
• PubChem CID: 71314770

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.21572456
• LogD (pH = 7.4): 0.21572456
• Log P: 0.21572456
• Molar Refractivity: 114.5732 cm^3
• Polarizability: 39.3847 Å^3
• Polar Surface Area: 33.02 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: White Solid
• Melting Point: >116°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C369340

N-Chloromethyl (S)-Citalopram is an impurity detected in Escitalopram (C505010) bulk drug.

REFERENCES

• Burke, W., et al.: J. Clin. Psychiary., 4, 20 (2002)
• Andersen, S., et al.: J. Pharm. Biomed. Sci., 33, 263 (2002)