62498-69-5

Basic information

• Product Name: DIDESMETHYL CITALOPRAM-D4
• Synonyms: DIDESMETHYL CITALOPRAM-D4;DIDESMETHYL CITALOPRAM HBR;1-(3-Aminopropyl)-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile;Didesmethylcitalopram;Dinorcitalopram;Lu 11-161;rac Didemethyl Citalopram;rac-Didesmethylcitalopram
• CAS NO: 62498-69-5
• Molecular Formula: C₁₈H₁₇FN₂O
• Molecular Weight: 296.34
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Isotope
• Mol File: 62498-69-5.mol

Chemical Properties

• Boiling Point: 433.1 °C at 760 mmHg
• Flash Point: 215.7 °C
• Appearance: /
• Density: 1.24 g/cm³
• Vapor Pressure: 1.05E-07mmHg at 25°C
• Refractive Index: 1.612
• CAS DataBase Reference: DIDESMETHYL CITALOPRAM-D4(CAS DataBase Reference)
• NIST Chemistry Reference: DIDESMETHYL CITALOPRAM-D4(62498-69-5)
• EPA Substance Registry System: DIDESMETHYL CITALOPRAM-D4(62498-69-5)

Safety Data

• Hazardous Substances Data: 62498-69-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
DIDESMETHYL CITALOPRAM-D4 is used as an antidepressant for the treatment of depression. As a metabolite of Citalopram, it contributes to the overall efficacy of the drug in modulating serotonin levels in the brain, thereby alleviating depressive symptoms and improving the patient's mood and overall well-being.

InChI:InChI=1/C18H17FN2O/c19-16-5-3-15(4-6-16)18(8-1-9-20)17-7-2-13(11-21)10-14(17)12-22-18/h2-7,10H,1,8-9,12,20H2

Upstream product

• 64169-66-0 5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran 
• 64169-67-1 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile 
• 14753-26-5 3-chloropropan-1-amine 

Downstream Products

• 1348805-33-3 BOC-didesmethylcitalopram 
• 526204-39-7 didesmethylcitalopram L-tartrate 
• 59729-33-8 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile 
• 166037-78-1 (+)-Didemethylcitalopram 
• 166037-77-0 (-)-Didemethylcitalopram 
• 392286-28-1 N-{3-[5-Cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl]-1-propyl}glycine ethyl ester 
• 928652-54-4 C₁₈H₁₇FN₂O*C₂₀H₁₈O₈ 
• 928652-45-3 C₁₈H₁₇FN₂O*C₂₀H₁₈O₈ 

Relevant articles and documents

Improved syntheses of N-desmethylcitalopram and N,N-didesmethylcitalopram

An improved and efficient synthesis of N-desmethylcitalopram (2) and N,N-didesmethylcitalopram (3) is presented. The method involved N-demethylation of citalopram (1) using 1-chloroethyl chloroformate to give 2 in 87% yield. Synthesis of 3 was accomplished by alkylation of 8 with 1-(3-bromopropyl)-2,2,5, 5-tetramethyl-1-aza-2,5-disilacyclopentane (9). Copyright Taylor & Francis Group, LLC.

Treatment or prophylaxis of migraine or headache disorders using citalopram, escitalopram or citalopram metabolites

Methods for prophylaxis of or treating or preventing migraine or migraine headaches, or other headache disorders include administering to a subject in need of treatment a therapeutically effective amount of citalopram, escitalopram, or a racemic or optically pure citalopram metabolite, or pharmaceutically acceptable salts, solvates, polymorphs, or hydrates thereof.

PREPARATION OF ESCITALOPRAM

Enantiomerically enriched citalopram is prepared by methylating enantiomerically enriched didesmethylcitalopram, obtained by directly resolving racemic didesmethylcitalopram using a chiral acid.

Method for the preparation of citalopram

The invention relates to a method for the preparation of citalopram comprising reaction of a compound of formula II with a compound having the formula wherein R is halogen or —O—SO2-X, wherein X is alkyl, alkenyl, alkynyl or optionally alkyl substituted aryl or aralkyl, and R1 is dimethylamino, halogen, —O—SO2-X wherein X is as defined above, provided that R is not halogen when R1 is dimethylamino; and if R1 is dimethylamino followed by isolation of citalopram base or a pharmaceutically acceptable acid addition salt thereof, and if R1 is halogen or —O—SO2-X, wherein X is as defined above, followed by conversion of the resulting compound of formula wherein R2 is halogen or a group of formula —O—SO2-X wherein X is as defined above to citalopram, followed by isolation of citalopram base or a pharmaceutically acceptable acid addition salt thereof.