16141-90-5

Usage

Uses

Used in Pharmaceutical Production:
1-(4-Fluorophenyl)piperazine hydrochloride is used as an active pharmaceutical ingredient for the development of medications that target the reuptake of neurotransmitters. Its role in inhibiting the reuptake of serotonin and norepinephrine makes it a key component in the treatment of conditions such as depression, anxiety, and other mood disorders.
Used in Neuroscience Research:
In the field of neuroscience, 1-(4-Fluorophenyl)piperazine hydrochloride is used as a research tool to study the effects of neurotransmitter reuptake inhibition on brain function. It helps researchers understand the complex interactions between neurotransmitters and the nervous system, contributing to the advancement of knowledge in neurobiology.
Used in Psychopharmacology:
1-(4-Fluorophenyl)piperazine hydrochloride is employed as a psychoactive substance in psychopharmacological studies. It is used to investigate the mechanisms of action of drugs that affect mood and behavior, providing insights into the development of novel therapeutic strategies for mental health disorders.
Used in Drug Safety and Toxicology Studies:
Due to its potential health hazards, 1-(4-Fluorophenyl)piperazine hydrochloride is also used in drug safety and toxicology research. It serves as a model compound to evaluate the risks associated with exposure to similar chemicals, guiding the development of safer pharmaceuticals and industrial chemicals.

InChI:InChI=1/C10H13FN2/c11-9-1-3-10(4-2-9)13-7-5-12-6-8-13/h1-4,12H,5-8H2

Upstream product

• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 
• 371-40-4 4-fluoroaniline 

Downstream Products

• 83082-17-1 6-<2-<4-(4-fluorophenyl)-1-piperazinyl>ethyl>-5,6,7,8-tetrahydro-1,6-naphthyridine 
• 83081-42-9 6-{3-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-propyl}-5,6,7,8-tetrahydro-[1,6]naphthyridine 
• 1163739-91-0 eremomycin AA₇-(4-(p-fluorophenyl)piperazin-1-yl)amide 
• 1092766-60-3 3-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}propyl-4-(4'-fluorophenyl)piperazine 
• 1092766-61-4 4-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}butyl-4-(4'-fluorophenyl)piperazine 
• 1092766-62-5 5-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}pentyl-4-(4'-fluorophenyl)piperazine 
• 120301-26-0 2-{4-[4-(4-fluorophenyl)piperazin-1-yl]butyl}-1H-isoindole-1,3(2H)-dione 

Relevant academic research and scientific papers

Design, synthesis, and systematic evaluation of 4-arylpiperazine- and 4-benzylpiperidine napthyl ethers as inhibitors of monoamine neurotransmitters reuptake

Two series of 4-arylpiperazine- and 4-benzylpiperidine naphthyl ethers were designed based on structure-activity relationship (SAR) and docking model of reported monoamine neurotransmitters reuptake inhibitors. The compounds were synthesized in 3-simple steps and their biological activities were evaluated. Several compounds were proven to be potent inhibitors of serotonin and norepinephrine reuptake. Computer docking was performed to study the interaction of the most potent compound 35 with human serotonin transporter. The results of the analyses suggest that 4-arylpiperazine- and 4-benzylpiperidine naphthyl ethers might be promising antidepressants worthy of further studies.

Design, synthesis, and evaluation of bitopic arylpiperazine-phthalimides as selective dopamine D3 receptor agonists

The dopamine D3 receptor (D3R) is a proven therapeutic target for the treatment of neurological and neuropsychiatric disorders. In particular, D3R-selective ligands that can eliminate side effects associated with dopamine D2 receptor (D2R) therapeutics have been validated. However, the high homology in signaling pathways and the sequence similarity between D2R and D3R have rendered the development of D3R-selective ligands challenging. Herein, we designed and synthesized a series of piperazine-phthalimide bitopic ligands based on a fragment-based and molecular docking inspired design. Compound 9i was identified as the most selective D3R ligand among these bitopic ligands. Its selectivity was improved compared to reference compounds 1 and 2 by 9- and 2-fold, respectively, and it was 21-fold more potent than compound 2. Molecular docking demonstrated that the orientation of Leu2.64 and Phe7.39 and the packing at the junction of helices may affect the specificity for D3R over D2R. Functional evaluation revealed that D3R-selective ligand 9i displayed a subpicomolar agonist activity at D3R with a 199-fold increase in potency compared to quinpirole. These results may be useful for the fragment-based design of bitopic compounds as selective D3R ligands.

Exploration of substituted arylpiperazine–tetrazoles as promising dual norepinephrine and dopamine reuptake inhibitors

In the search for potent dual norepinephrine and dopamine reuptake inhibitors, several substituted arylpiperazine–tetrazoles were designed, synthesized and evaluated for their neurotransmitter reuptake inhibitory activities. Various derivatives exhibited selective and strong neurotransmitter reuptake inhibitory activity. In particular, compounds with a three-carbon linker displayed selective and stronger potency than those with two-carbon and four-carbon linkers. Interestingly, six compounds, 9b, 9c, 9d, 9o, 9q and 9u displayed more effective activity than the standard drug, bupropion. The provided SAR data and potent biological activity can offer useful guidelines for designing dual norepinephrine and dopamine reuptake inhibitors as effective therapeutic agents for treatment of several central nervous system diseases.

Design, synthesis, and biological evaluation of arylpiperazine-benzylpiperidines with dual serotonin and norepinephrine reuptake inhibitory activities

The limitations of established serotonin (5-hydroxytryptamine, 5-HT) and norepinephrine (NE) reuptake inhibitors necessitate the development of safer and more effective therapeutic agents. Based on the structures of 4-benzylpiperidine carboxamides and trazodone, arylpiperazine-benzylpiperidines with chemical scaffolds different from those of marketed drugs were designed, synthesized, and evaluated for their neurotransmitter reuptake inhibitory activities. The majority of the synthesized compounds showed greater NE than 5-HT reuptake inhibition. The activities were even greater than those of the standard drug, venlafaxine hydrochloride were. The derivatives with a three-carbon linker showed better activities than the derivatives with a two-carbon linker. Among the newly synthesized compounds, 2d exhibited the strongest reuptake inhibition of the neurotransmitters (IC50 = 0.38 μM for NE and 1.18 μM for 5-HT). The biological activity data demonstrate that arylpiperazine-benzylpiperidines have the potential to be developed as a new class of therapeutic agents to treat neuropsychiatric and neurodegenerative disorders.

An efficient scale up process for synthesis of N-arylpiperazines

An efficient protocol for the synthesis of various substituted phenylpiperazines was developed using sulfolane as solvent. The protocol was clean, high yielding and products were obtained in high purities (≥99%). It was also fast and convenient, as the final products were precipitated as hydrochloride salts and could be obtained by filtration. Sulfolane, an aprotic, dipolar, high boiling and recoverable solvent was used as a substitute for common organic solvents.

Synthesis and biological evaluation of novel N-[3-(4-phenylpip-erazin-1-yl) -propyl]-carboxamide derivatives

A series of novel N-[3-(4-phenylpiperazin-1-yl)-propyl]-carboxamide derivatives were synthesised and studied for the potential treatment of HIV. These compounds were obtained through the efficient synthetic route that involved microwave assisted synthesis. These new compounds have been characterised by IR,1H NMR, MS and elemental analysis. The cell-cell fusion inhibitory activities of the compounds have also been evaluated.