title: Structural elucidation of process-related impurities in escitalopram by LC/ESI-MS and NMR.
abstract: Three impurities were detected in escitalopram bulk drug by HPLC-UV and LC/MS. These impurities were marked as ESC-I, -II and -III. Two of these impurities (ESC-II and -III) were unknown and have not been reported previously. Ion trap and Q-TOF mass analyzer were employed to carry out MS/MS and accurate mass analysis of these unknown impurities. Based on mass spectrometric data and synthetic specifics the structures of ESC-II and -III were proposed as N-(chloromethyl)-3-[5-cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]-N,N-dimethylpropan-1-aminium and N-(chloromethyl)-4-[4-cyano-2-(hydroxymethyl)phenyl]-4-(4-fluorophenyl)-4-hydroxy-N,N-dimethylbutan-1-aminium respectively. The impurities were isolated by semi-preparative HPLC and structures were confirmed by NMR spectroscopy. The plausible mechanism for the formation of impurities is also discussed.
authors.affiliation: Department of Chemistry, K. J. Somaiya College of Science and Commerce, Vidyavihar (E), Mumbai, India. drbhanuraman@rediffmail.com
authors.forename: Bhanu
authors.initials: B
authors.lastname: Raman
authors.forename: Brajesh A
authors.initials: BA
authors.lastname: Sharma
authors.forename: Pradeep D
authors.initials: PD
authors.lastname: Ghugare
authors.forename: Sanjay
authors.initials: S
authors.lastname: Nandavadekar
authors.forename: Dharmendra
authors.initials: D
authors.lastname: Singh
authors.forename: Pravin K
authors.initials: PK
authors.lastname: Karmuse
authors.forename: Ashok
authors.initials: A
authors.lastname: Kumar
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D015283:Citalopram / Q000032:analysis*; D004340:Drug Contamination; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D017367:Selective Serotonin Reuptake Inhibitors / Q000032:analysis*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*
chemical_list: D015283:Citalopram; D017367:Selective Serotonin Reuptake Inhibitors