80125-14-0

Basic information

• Product Name: Remoxipride
• Synonyms: (S)-Remoxipride;3-Bromo-2,6-dimethoxy-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]benzamide;3-Bromo-2,6-dimethoxy-N-[[[2S,(-)]-1-ethylpyrrolidine-2α-yl]methyl]benzamide;3-Bromo-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-2,6-dimethoxybenzamide;(S)-3-BroMo-N-((1-ethylpyrrolidin-2-yl)Methyl)-2,6-diMethoxybenzaMide;REMOXIPRIDE;Remoxipride [USAN:BAN:INN];(S)-3-Bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2，6-dimethoxybenzamide
• CAS NO: 80125-14-0
• Molecular Formula: C₁₆H₂₃BrN₂O₃
• Molecular Weight: 371.27
• Mol File: 80125-14-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 439.9°C at 760 mmHg
• Flash Point: 219.8°C
• Appearance: /
• Density: 1.292
• Vapor Pressure: 6.17E-08mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: 2-8°C
• PKA: pKa 8.9 (Uncertain)
• CAS DataBase Reference: Remoxipride(CAS DataBase Reference)
• NIST Chemistry Reference: Remoxipride(80125-14-0)
• EPA Substance Registry System: Remoxipride(80125-14-0)

Safety Data

• Hazardous Substances Data: 80125-14-0(Hazardous Substances Data)

Usage

Uses

Antipsychotic.

General Description

Remoxipride is a D2 receptorblocker.It is as effective as haloperidol with fewer EPS andautonomic side effects. Negative symptoms of schizophreniaare diminished. The drug is classed as an atypical antipsychotic.Life-threatening aplastic anemia was reported with itsuse, which prompted its withdrawal from the market.With respect to the atypical antipsychotics, two eventslong in the past may shed some light on the events of today.The field of reuptake-inhibiting antidepressants arose whenonly a very small structural change was made in an antipsychoticdrug, and the new activity noted. (The antipsychoticactivity remained.) Therefore, small changes in structurecan produce antipsychotics that are active against depressivesymptoms. Likewise, small changes in structure could provideselectivity among D2 receptors.

InChI:InChI=1/C16H23BrN2O3/c1-4-19-9-5-6-11(19)10-18-16(20)14-13(21-2)8-7-12(17)15(14)22-3/h7-8,11H,4-6,9-10H2,1-3H3,(H,18,20)

Upstream product

• 73219-89-3 3-bromo-2,6-dimethoxybenzoic acid 
• 22795-99-9 (S)-2-(Aminomethyl)-1-ethylpyrrolidine 
• 84225-91-2 5-bromo-2,6-dimethoxybenzoic acid chloride 
• 84277-13-4 di-D-(-)-tartrate salt of (S)-2-aminomethyl-1-ethylpyrrolidine 
• 1466-76-8 2-6-dimethoxybenzoic acid 

Relevant articles and documents

3-Aminomethylbiphenyls. A New Class of Dopamine Receptor Ligands

A series of 3-aminomethylbiphenyls were prepared in three steps from 3-phenylbenzoic acid and their affinities for the D2, D3 and D4 dopamine receptor subtypes determined. Most of the compounds described contained unique amine subunits of known dopaminergic agents. The compounds containing the amino tails present in the antipsychotic drugs haloperidol, pimozide and miliperidine displayed selectivity for the D2 receptor. Five-fold selectivity for the D4 receptor was observed in the compound 1-(3-biphenyl)-4-(2-pyrimidyl)piperazine. This selectivity for D4 vs. D2 receptors is comparable to that observed with the atypical antipsychotic clozapine.