827614-48-2

Basic information

• Product Name: 1-(2,4-DICHLOROPHENYL)-PIPERAZINE DIHYDROCHLORIDE
• Synonyms: 1-(2,4-Dichlorophenyl)piperazinedihydrochloride 1-(2,4-Dichlorophenyl)-piperazine dihydrochloride 1-(2,4-Dichloro-phenyl)-piperazine dihydrochloride;1-(2,4-Dichlorophenyl)piperazine dihydrochloride;4-dichlorophenyl)piperazine dihydrochloride;1-(2,4-DICHLOROPHENYL)PIPERAZINE 2HCL
• CAS NO: 827614-48-2
• Molecular Formula: C10H14Cl4N2
• Molecular Weight: 304.04
• Mol File: 827614-48-2.mol

Chemical Properties

• Boiling Point: 362.6 °C at 760 mmHg
• Flash Point: 173.1 °C
• Appearance: /
• Vapor Pressure: 1.91E-05mmHg at 25°C
• CAS DataBase Reference: 1-(2,4-DICHLOROPHENYL)-PIPERAZINE DIHYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4-DICHLOROPHENYL)-PIPERAZINE DIHYDROCHLORIDE(827614-48-2)
• EPA Substance Registry System: 1-(2,4-DICHLOROPHENYL)-PIPERAZINE DIHYDROCHLORIDE(827614-48-2)

Safety Data

• Hazardous Substances Data: 827614-48-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(2,4-Dichlorophenyl)-piperazin dihydrochloride is used as an intermediate in the preparation of various pharmaceuticals for its ability to facilitate the synthesis of active drug compounds.
Used in Psychiatric Disorders Treatment:
In the field of psychiatry, 1-(2,4-Dichlorophenyl)-piperazin dihydrochloride is used as a potential therapeutic agent for the treatment of various psychiatric disorders, including anxiety and depression, due to its potential anxiolytic and antidepressant properties.
Used in Antipsychotic Drug Development:
1-(2,4-Dichlorophenyl)-piperazin dihydrochloride is also being investigated for its potential as an antipsychotic agent, highlighting its utility in the development of medications aimed at managing psychotic symptoms in conditions such as schizophrenia.

InChI:InChI=1/C10H12Cl2N2.2ClH/c11-8-1-2-10(9(12)7-8)14-5-3-13-4-6-14;;/h1-2,7,13H,3-6H2;2*1H

Upstream product

• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 
• 554-00-7 2,4-Dichloroaniline 

Relevant articles and documents

Design, synthesis and docking study of 4-arylpiperazine carboxamides as monoamine neurotransmitters reuptake inhibitors

Rational drug design method has been used to generate 4-arylpiperazine carboxamides in an effort to develop safer, more potent and effective monoamine neurotransmitters reuptake inhibitors. Out of twenty-seven synthesized compounds, compound 9 displayed potent monoamine neurotransmitter reuptake inhibitory activity against HEK cells transfected with hSERT or hNET. A Surflex-Dock docking model of 9 was also studied.

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.

Design, synthesis and in vitro activity of 1,4-disubstituted piperazines and piperidines as triple reuptake inhibitors

Monoamine transporters regulate the concentration of monoamine neurotransmitters, which are essential for vital physiological processes, and their dysfunction can cause several central nervous system diseases. Monoamine transporters currently appear to be the potential target in the management of these disorders. In this study, homologation and bioisosterism techniques have been used in the designing of new 1,4-disubstituted piperazines and piperidines. These derivatives were synthesized and evaluated as potential triple reuptake inhibitors for studying the structure-activity relationships. The most advanced compound, 1-(4-(5-benzhydryl-1H-tetrazol-1-yl)butyl)-4-(3-phenylpropyl)piperazine (2i), was able to inhibit monoamine neurotransmitter reuptake in an in vitro test (IC50?=?158.7?nM for 5-HT, 99?nM for NE and 97.5?nM for DA). These novel potent triple reuptake inhibitor-based 1,4-disubstituted piperazine and piperidine scaffolds deserve further systematic optimization and pharmacological evaluation.

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.