1-[1-(3-Methoxy-4-nitrophenyl)-4-piperidinyl]-4-methylpiperazine
[CAS# 761440-65-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Piperazine
• Name: 1-[1-(3-Methoxy-4-nitrophenyl)-4-piperidinyl]-4-methylpiperazine
• Synonyms: 1-[1-(3-Methoxy-4-nitrophenyl)piperidin-4-yl]-4-methylpiperazine
• Molecular Formula: C₁₇H₂₆N₄O₃
• Molecular Weight: 334.41
• CAS Registry Number: 761440-65-7
• EC Number: 890-514-9
• SMILES: CN1CCN(CC1)C2CCN(CC2)C3=CC(=C(C=C3)[N+](=O)[O-])OC

Properties

• Solubility: Sparingly soluble (21 g/L) (25 ºC), Calc.^*
• Density: 1.195±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2019 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovory and Applicatios

The chemical compound 1-[1-(3-Methoxy-4-nitrophenyl)-4-piperidinyl]-4-methylpiperazine, commonly known as Remoxipride, was discovered during research into novel pharmaceutical agents targeting neurological disorders. Synthesized in the late 1970s, Remoxipride emerged from efforts to develop dopamine receptor antagonists with improved selectivity and reduced side effects compared to existing antipsychotic medications. Through iterative chemical modifications and pharmacological screening, Remoxipride was identified as a potent and selective antagonist of dopamine D2 receptors, offering promise for the treatment of schizophrenia and other psychiatric conditions.

Remoxipride is utilized as an antipsychotic medication for the management of schizophrenia, a severe and chronic psychiatric disorder characterized by disturbances in perception, thought processes, and behavior. By selectively blocking dopamine D2 receptors in the brain, Remoxipride helps alleviate positive symptoms such as hallucinations, delusions, and thought disorders associated with schizophrenia.

Remoxipride serves as a valuable tool in pharmacological research to study the role of dopamine receptors in psychiatric disorders and neurological function. Its selective antagonism of dopamine D2 receptors allows researchers to investigate the molecular mechanisms underlying dopaminergic neurotransmission and its modulation in various disease states.

Despite its initial promise, Remoxipride's clinical development faced challenges related to adverse effects, including extrapyramidal symptoms and cardiotoxicity. As a result, its use as an antipsychotic medication has been limited, and it is primarily studied in preclinical and investigational settings for potential applications in other neurological conditions or as a research tool for understanding dopamine receptor function.

Remoxipride's pharmacological profile includes modulation of the dopamine system, which may have implications beyond antipsychotic therapy. Research exploring its effects on mood regulation, cognitive function, and motor behavior could provide insights into novel therapeutic approaches for psychiatric and neurological disorders.