2-Methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]aniline
[CAS# 761440-75-9]

Identification

• Classification: Organic raw materials >> Amino compound >> Cycloalkylamines, aromatic monoamines, aromatic polyamines and derivatives and salts
• Name: 2-Methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]aniline
• Synonyms: [2-Methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]amine
• Molecular Formula: C₁₇H₂₈N₄O
• Molecular Weight: 304.43
• CAS Registry Number: 761440-75-9
• SMILES: CN1CCN(CC1)C2CCN(CC2)C3=CC(=C(C=C3)N)OC

Properties

• Solubility: Soluble (94 g/L) (25 °C), Calc.^*
• Density: 1.126±0.06 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

2-Methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]aniline, commonly known as Trazodone, was discovered in the 1960s during research into novel antidepressant medications. Chemists were exploring structural modifications of existing psychoactive compounds to develop safer and more effective treatments for depression and anxiety disorders. Through systematic synthesis and pharmacological screening, Trazodone was identified as a potent serotonin antagonist and reuptake inhibitor (SARI), exerting its therapeutic effects by modulating serotonin neurotransmission in the brain.

Trazodone is widely prescribed as an antidepressant medication for the treatment of major depressive disorder (MDD), a common psychiatric condition characterized by persistent feelings of sadness, hopelessness, and loss of interest or pleasure in daily activities. By inhibiting the reuptake of serotonin and antagonizing serotonin receptors, Trazodone helps alleviate depressive symptoms and improve mood in patients with MDD. Trazodone may also be used as an adjunctive therapy in combination with other antidepressant medications or mood stabilizers to enhance treatment efficacy and address specific symptoms, such as insomnia or anxiety, in patients with treatment-resistant depression or comorbid psychiatric conditions.

Trazodone is commonly prescribed off-label for the treatment of insomnia, particularly in patients who experience difficulty falling asleep or maintaining sleep continuity. Its sedative properties and favorable side effect profile make it a preferred choice for promoting sleep onset and improving sleep quality in individuals with insomnia. In some cases, Trazodone may be used off-label to manage symptoms of anxiety disorders, such as generalized anxiety disorder (GAD) or post-traumatic stress disorder (PTSD). Its serotonin modulating effects may help alleviate anxiety symptoms and improve overall psychological well-being in certain patient populations.

Trazodone serves as a valuable tool in pharmacological research to study the role of serotonin neurotransmission in mood regulation and psychiatric disorders. Its unique pharmacological profile as a SARI allows researchers to investigate the molecular mechanisms underlying antidepressant efficacy and explore potential targets for novel therapeutic interventions.

Beyond its use as an antidepressant and hypnotic agent, Trazodone is studied in sleep medicine for its effects on sleep architecture, sleep continuity, and rapid eye movement (REM) sleep suppression. Research into its mechanisms of action and long-term effects on sleep parameters may provide insights into its potential applications in the management of sleep disorders.

References

2021. A Novel and Highly Selective FAK Inhibitor. Synfacts, 17(3).
DOI: 10.1055/s-0040-1719409

2017. Brigatinib. Pharmaceutical Substances
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-02-0179