144010-85-5

Usage

Uses

Used in Pharmaceutical Industry:
R-DESMETHYLCITALOPRAM is used as an antidepressant for treating depression and other mood disorders. It functions by inhibiting the reuptake of serotonin, thereby increasing its availability in the synaptic cleft and enhancing mood regulation.
R-DESMETHYLCITALOPRAM is used as an active pharmaceutical ingredient (API) for the development of antidepressant medications. Its role in modulating serotonin levels makes it a crucial component in the treatment of depression and related mood disorders, providing relief and improving the quality of life for patients suffering from these conditions.

InChI:InChI=1/C19H19FN2O.ClH/c1-22-10-2-9-19(16-4-6-17(20)7-5-16)18-8-3-14(12-21)11-15(18)13-23-19;/h3-8,11,22H,2,9-10,13H2,1H3;1H/t19-;/m1./s1

Upstream product

• 59729-33-8 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile 
• 59729-32-7 citalopram hydrobromide 
• 1101848-95-6 (S)-(+)-1-(4-fluorophenyl)-1-(3-methylaminopropyl)-1,3-dihydroisobenzofuran-5-carbonitrile, (-)-di-p-toluoyl-D-tartaric acid salt 
• 1084839-40-6 (+)-desmethyl citalopram DPTTA salt 
• 62498-67-3 rac-desmethylcitalopram 
• 219861-08-2 escitalopram oxalate 
• 1425794-07-5 C₂₂H₂₂ClFN₂O₃ 
• 128196-01-0 escitalopram 
• 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 

Downstream Products

• 144025-14-9 (+)-Desmethylcitalopram 
• 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 
• 166037-77-0 (-)-Didemethylcitalopram 
• 166037-78-1 (+)-Didemethylcitalopram 
• 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 

Relevant academic research and scientific papers

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.

Effect of CYP2D6 genetic polymorphism on the metabolism of citalopram in vitro

Genetic polymorphisms of CYP2D6 significantly influence the efficacy and safety of some drugs, which might cause adverse effects and therapeutic failure. We aimed at investigating the role of CYP2D6 in the metabolism of citalopram and identifying the effect of 24 CYP2D6 allelic variants we found in Chinese Han population on the metabolism of citalopram in vitro. These CYP2D6 variants expressed by insect cells system were incubated with 10-1000 μM citalopram for 30 min at 37 °C and the reaction was terminated by cooling to -80 °C immediately. Citalopram and its metabolites were analyzed by high-performance liquid chromatography (HPLC). The intrinsic clearance (Vmax/Km) values of the variants toward citalopram metabolites were significantly altered, 38-129% for demethylcitalopram and 13-138% for citalopram N-oxide when compared with CYP2D6?1. Most of the tested rare alleles exhibited significantly decreased values due to increased Km and/or decreased Vmax values. We conclude that recombinant system could be used to investigate the enzymes involved in drug metabolism and these findings suggest that more attention should be paid to subjects carrying these CYP2D6 alleles when administering citalopram in the clinic.

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.

Antiprotozoal amidine compounds

The invention is directed to a compound of formula I, as defined herein, or a pharmaceutically acceptable salt thereof; a pharmaceutical composition containing a compound of formula I, a method of treatment of a disorder or condition that may be treated by administration of the compound, the method comprising administering to a mammal in need of such treatment a compound of formula I as described above, and a method of treatment of a disorder or condition selected from the group consisting of Human African Trypanosomiasis (HAT), Chagas disease, malaria and Leishmaniasis, the method comprising administering to a mammal, including a human, in need of such treatment a compound of formula I as described above.

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

Design and synthesis of 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3- dihydroisobenzofuran-5-carbonitrile (citalopram) analogues as novel probes for the serotonin transporter S1 and S2 binding sites

The serotonin transporter (SERT) is the primary target for antidepressant drugs. The existence of a high affinity primary orthosteric binding site (S1) and a low affinity secondary site (S2) has been described, and their relation to antidepressant pharmacology has been debated. Herein, structural modifications to the N, 4, 5, and 4′ positions of (±)citalopram (1) are reported. All of the analogues were SERT-selective and demonstrated that steric bulk was tolerated at the SERT S1 site, including two dimeric ligands (15 and 51). In addition, eight analogues were identified with similar potencies to S-1 for decreasing the dissociation of [3H]S-1 from the S1 site via allosteric modulation at S2. Both dimeric compounds had similar affinities for the SERT S1 site (Ki = 19.7 and 30.2 nM, respectively), whereas only the N-substituted analogue, 51, was as effective as S-1 in allosterically modulating the binding of [3H]S-1 via S2.

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).