144025-14-9

Basic information

• Product Name: DEMETHYLCITALOPRAM
• Synonyms: DEMETHYLCITALOPRAM;1-(4-Fluoro-phenyl)-1-(3-methylamino-propyl)-1,3-dihydro-isobenzofuran-5-carbonitril;rac Demethyl Citalopram;S-Desmethylcitalopram;1-(4-Fluoro-phenyl)-1-(3-methylamino-propyl)-1,3-dihydro-isobenzofuran-5-carbonitrile Hydrochloride;racDemethyl Citalopram Hydrochloride;1-(3-Methylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile;1-(4-Fluoro-phenyl)-1-(3-methylamino-propyl)-1,3-dihydro-isobenzofuran-5-carbonitrile
• CAS NO: 144025-14-9
• Molecular Formula: C₁₉H₁₉FN₂O
• Molecular Weight: 310.37
• Product Categories: Various Metabolites and Impurities;Chiral Reagents;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 144025-14-9.mol

Chemical Properties

• Melting Point: 60-65°C
• Boiling Point: 429.4±45.0 °C(Predicted)
• Flash Point: 9℃
• Appearance: /
• Density: 1.20±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• PKA: 10.50±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: DEMETHYLCITALOPRAM(CAS DataBase Reference)
• NIST Chemistry Reference: DEMETHYLCITALOPRAM(144025-14-9)
• EPA Substance Registry System: DEMETHYLCITALOPRAM(144025-14-9)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 1
• Hazardous Substances Data: 144025-14-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
DEMETHYLCITALOPRAM is used as an antidepressant for the treatment of major depression associated with mood disorders. It acts by inhibiting the reuptake of serotonin, a neurotransmitter responsible for regulating mood, appetite, and sleep, among other functions. This increased availability of serotonin in the synaptic cleft helps alleviate the symptoms of depression and improve the overall well-being of the patient.
DEMETHYLCITALOPRAM is used as a metabolite in the development and understanding of the pharmacological effects of Citalopram. As an active metabolite, it contributes to the overall efficacy of the parent drug, Citalopram, in treating depression and mood disorders. This knowledge aids researchers and pharmaceutical companies in the development of more effective and targeted antidepressant medications.
In addition to its use as an antidepressant, DEMETHYLCITALOPRAM may also be utilized in research studies to better understand the mechanisms of action and potential side effects of SSRI antidepressants. This information can be valuable in the development of new treatments and therapies for depression and other mood disorders.
Overall, DEMETHYLCITALOPRAM plays a crucial role in the pharmaceutical industry as a component of antidepressant medications and as a subject of research for the advancement of mental health treatments.

Upstream product

• 1084839-40-6 (+)-desmethyl citalopram DPTTA salt 
• 1101848-95-6 (S)-(+)-1-(4-fluorophenyl)-1-(3-methylaminopropyl)-1,3-dihydroisobenzofuran-5-carbonitrile, (-)-di-p-toluoyl-D-tartaric acid salt 
• 128196-01-0 escitalopram 
• 219861-08-2 escitalopram oxalate 
• 59729-32-7 citalopram hydrobromide 
• 62498-67-3 rac-desmethylcitalopram 
• 1425794-07-5 C₂₂H₂₂ClFN₂O₃ 
• 190197-86-5 4-bromo-3-(bromomethyl)benzonitrile 
• 41963-20-6 4-bromo-3-methylbenzonirtile 
• 1352344-90-1 C₂₉H₃₇FN₂O₅ 
• 1352344-88-7 C₂₃H₃₇FN₂O₄ 
• 1352344-87-6 C₁₆H₂₄FNO₃ 
• 1352344-86-5 C₁₆H₂₀FNO₃ 
• 1352344-85-4 C₁₉H₂₆BNO₄ 

Downstream Products

• 166037-78-1 (+)-Didemethylcitalopram 
• 128196-01-0 escitalopram 
• 1425794-14-4 (S)-(3-(5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)propyl)dimethylselenonium trifluoromethanesulfonate 
• 1425794-09-7 (S)-1-(4-fluorophenyl)-1-(3-(methylthio)propyl)-1,3-dihydroisobenzofuran-5-carbonitrile 
• 1425794-12-2 (S)-1-(4-fluorophenyl)-1-(3-(methyselanyl)propyl)-1,3-dihydroisobenzofuran-5-carbonitrile 
• 1425794-11-1 (S)-(3-(5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)propyl)dimethylsulfonium trifluoromethanesulfonate 
• 1585941-23-6 (S)-1-(3-((3-(1,3-dioxoisoindolin-2-yl)propyl)(methyl)amino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile 
• 1585941-24-7 (S)-1-(3-((5-(1,3-dioxoisoindolin-2-yl)pentyl)(methyl)amino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile 
• 1585941-25-8 (S)-1-(3-((3-aminopropyl)(methyl)amino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile 
• 1585941-26-9 (S)-1-(3-((5-aminopentyl)(methyl)amino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile 

Relevant articles and documents

Preparation method of escitalopram oxalate demethylation impurity

The invention provides a brand-new preparation method of 1-(4- fluorophenyl)-1-(3-(fluorophenyl)propyl)-1,3-dihydroisobenzofiaran-5-formonitrile as an escitalopram oxalate process impurity. The brand-new preparation method provides a reference for qualitatively and quantitatively analyzing impurity conditions in a finished product of escitalopram oxalate, has an important effect on quality control of the escitalopram oxalate, and can promote safe medication of depressed patients.

Design, synthesis, and biological evaluation of a series of bifunctional ligands of opioids/SSRIs

A series of opioid and serotonin re-uptake inhibitors (SSRIs) bifunctional ligands have been designed, synthesized, and tested for their activities and efficacies at μ-, δ- and κ opioid receptors and SSRIs receptors. Most of the compounds showed high affinities for μ- and δ-opioid receptors and lower affinities for SSRIs and κ opioid receptors. A docking study on the μ-opioid receptor binding pocket has been carried out for ligands 3-11. The ligands 7 and 11 have displayed the highest binding profiles for the μ-opioid receptor binding site with ΔGbind (-12.14 kcal/mol) and Ki value (1.0 nM), and ΔGbind (-12.41 kcal/mol) and Ki value (0.4 nM), respectively. Ligand 3 was shown to have the potential of dual acting serotonin/norepinephrine re-uptake inhibitor (SNRI) antidepressant activity in addition to opioid activities, and thus could be used for the design of multifunctional ligands in the area of a novel approach for the treatment of pain and depression.

Novel and high affinity fluorescent ligands for the serotonin transporter based on (S)-citalopram

Novel rhodamine-labeled ligands, based on (S)-citalopram, were synthesized and evaluated for uptake inhibition at the human serotonin, dopamine, and norepinephrine transporters (hSERT, hDAT, and hNET, respectively) and for binding at SERT, in transiently

PERMANENTLY POSITIVELY CHARGED ANTIDEPRESSANTS

The present invention provides compounds comprising a substructure of below formula 3: or a salt or prodrug thereof and the use of such compounds in treatment of e.g. CNS disorders.

Enantioenriched synthesis of Escitalopram using lithiation-borylation methodology

The asymmetric synthesis of Escitalopram has been completed using a lithiation-borylation reaction as the key step. Suitably functionalized enantioenriched carbamate (er 98:2) and boronic ester coupling partners were prepared and following deprotonation with s-BuLi and borylation, the tertiary alcohol was obtained in 42% yield and 93:7 er. The lithiation-borylation reaction was found to tolerate nitrile, benzylic alcohol and N-Boc functionalities. The tertiary alcohol was converted to Escitalopram in three further steps.

Process for the Preparation of Escitalopram

The present invention provides a novel process for the preparation of a compound of Formula III, and novel processes for preparing escitalopram using the compound of Formula III.

Process for the preparation of escitalopram

The present invention relates to a novel process for the preparation of Escitalopram, which comprises: (ii) de-methylating (±)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile (Formula II) (Citalopram) to produce (±)-1-[3-(methylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile (desmethyl Citalopram) (XII), (iii) isolating the pure desmethyl Citalopram (XII), (iv) separating the enantiomers from the pure desmethyl Citalopram (XII) with an optically active acid to obtain (S)-(+)-1-[3-(methylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile ((S)-(+)-desmethyl Citalopram) (XIII), (v) methylating an enantiomerically pure compound (XIII) using suitable methylating agent to produce Escitalopram (I).

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.

Gas phase production of [11C]methyl iodide-d3. Synthesis and biological evaluation of S-[N-methyl-11C]citalopram and deuterated analogues

Three 11C-labelled tracers for the serotonin reuptake site, S-[N-methyl-11C]citalopram ([11C]-4), S-[N-methyl-d 3-11C]citalopram ([11C]-12), and S-[N-methyl-11C]citalopram-α,α-d

Studies on the stereoselective metabolism of citalopram by human liver microsomes and cDNA-expressed cytochrome P450 enzymes

The involvement of CYP enzymes in the metabolism of citalopram was studied, inclusive the conversion of demethylcitalopram to didemethylcitalopram and the formation of citalopram N-oxide, which both have not been considered previously. Using human mixed liver microsomes and cDNA-expressed CYP enzymes, we confirmed that CYP3A4, 2C19 and 2D6 are involved in the first demethylation step of citalopram, all favouring conversion of the biologically active S-enantiomer. Inhibitor studies indicated that at therapeutic citalopram concentrations CYP3A4 was responsible for 40-50% of demethylcitalopram formation, while the contribution of CYP2C19 increased and that of CYP2D6 tended to decrease with increasing drug concentration, CYP2D6 exclusively mediated the second demethylation step, and citalopram N-oxide was also exclusively formed by CYP2D6. None of the studied CYP enzymes mediated deamination to the propionic acid derivative.