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80125-14-0

80125-14-0 Structure

80125-14-0 Structure
IdentificationMore
[Name]

Remoxipride
[CAS]

80125-14-0
[Synonyms]

REMOXIPRIDE
Remoxipride [USAN:BAN:INN]
(S)-3-Bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,6-dimethoxybenzamide
A-33547
FLA-731
Roxiam
(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
[Molecular Formula]

C16H23BrN2O3
[MDL Number]

MFCD00869705
[Molecular Weight]

371.27
[MOL File]

80125-14-0.mol
Chemical PropertiesBack Directory
[alpha ]

D20 -64° (c = 2 in ethanol)
[Boiling point ]

439.9±45.0 °C(Predicted)
[density ]

1.292
[storage temp. ]

2-8°C
[pka]

pKa 8.9 (Uncertain)
[CAS DataBase Reference]

80125-14-0(CAS DataBase Reference)
[NIST Chemistry Reference]

Remoxipride(80125-14-0)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Thionyl chloride-->2,6-Dimethoxybenzoic acid-->2-(Aminomethyl)-1-ethylpyrrolidine
Hazard InformationBack Directory
[Uses]

Antipsychotic.
[Definition]

ChEBI: 3-bromo-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-2,6-dimethoxybenzamide is a dimethoxybenzene.
[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.
[in vivo]

(S)-Remoxipride (0.1-100 μM/kg; i.p. 60 min prior to apomorphine) blockades apomorphine-induced behaviors s in rats and vomiting in dogs[1]. (S)-Remoxipride (0.1-10 mg/kg; i.p. 30 min prior to apomorphine) displaces [3H]spiperone from both striatal and extra-striatal areas[1].

Animal Model:Male Sprague-Dawley rats[1]
Dosage:0.1-100 μM/kg
Administration:Intraperitoneal injection; 0.1-100 μM/kg; 60 min prior to apomorphine
Result:Blocked apomorphine-induced hyperactivity and dose-dependent blockaded apomorphine-induced behaviors in vivo.
Animal Model:Male and female beagle dogs[1]
Dosage:0.25-5 μM/kg
Administration:Oral gavage; 0.25-5 μM/kg; 60 min prior to apomorphine
Result:Blocked apomorphine-induced vomiting in dogs.
[IC 50]

D2 Receptor: 1.57 μM (IC50); D1 Receptor: >100 μM (IC50); α1-Adrenoccptor: 42 μM (IC50)
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