440121-09-5

Basic information

• Product Name: CitalopraM carboxylic acid iMpurity
• Synonyms: CitalopraM carboxylic acid iMpurity
• CAS NO: 440121-09-5
• Molecular Formula: C20H22FNO3
• Molecular Weight: 343.3919832
• Mol File: 440121-09-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: CitalopraM carboxylic acid iMpurity(CAS DataBase Reference)
• NIST Chemistry Reference: CitalopraM carboxylic acid iMpurity(440121-09-5)
• EPA Substance Registry System: CitalopraM carboxylic acid iMpurity(440121-09-5)

Safety Data

• Hazardous Substances Data: 440121-09-5(Hazardous Substances Data)

Usage

General Description

Citalopram carboxylic acid is an impurity that can be found in the antidepressant medication Citalopram. It is formed as a metabolite of Citalopram in the body and can also be present as a impurity in the drug substance. This impurity is a carboxylic acid derivative and is known to have minimal pharmacological activity compared to the parent compound. However, it is important to monitor its levels in medication as higher concentrations of Citalopram carboxylic acid impurity can potentially lead to adverse effects on the body. Therefore, it is essential for pharmaceutical manufacturers to ensure that the levels of this impurity in Citalopram-containing medications are within acceptable limits to ensure the safety and efficacy of the drug.

Upstream product

• 59729-33-8 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile 
• 64372-56-1 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxamide 
• 128196-01-0 escitalopram 

Downstream Products

• 936846-17-2 C₂₀H₂₂FNO₂ 
• 1329745-98-3 (S)-4-dimethylamino-1-{1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-yl}-1-butanone 

Relevant articles and documents

Of escitalopram oxalate-related substance and its preparation method

The invention relates to an escitalopram oxalate related substance and a preparation method thereof, and particularly, relates to the related substance of an antidepressant drug, the escitalopram oxalate (namely, (S)-(+)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-formonitrile oxalate), represented as the formula (I) and a preparation method thereof. The escitalopram oxalate, as the target compound, is synthesized through reactions comprising hydrolysis, acylation, condensation, reduction, addition and oxidization to the compound (II) (namely, (S)-(+)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-formonitrile). According to the method, the compound (I) is chemically synthesized for the first time. By means of the method, the target compound can be obtained through high-efficient and quick separation.

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.