20529-19-5

Basic information

• Product Name: 3-(4-phenylpiperazin-1-yl)propan-1-amine
• Synonyms: 3-(4-phenylpiperazin-1-yl)propan-1-amine;3-(4-phenyl-1-piperazinyl)-1-propanamine;3-(4-phenyl-1-piperazinyl)propan-1-amine;3-(4-phenyl-1-piperazinyl)propylamine
• CAS NO: 20529-19-5
• Molecular Formula: C₁₃H₂₁N₃
• Molecular Weight: 219.33
• Mol File: 20529-19-5.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 355.3°Cat760mmHg
• Flash Point: 166.2°C
• Appearance: /
• Density: 1.041g/cm³
• Vapor Pressure: 3.15E-05mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: 3-(4-phenylpiperazin-1-yl)propan-1-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-phenylpiperazin-1-yl)propan-1-amine(20529-19-5)
• EPA Substance Registry System: 3-(4-phenylpiperazin-1-yl)propan-1-amine(20529-19-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 20529-19-5(Hazardous Substances Data)

Usage

General Description

3-(4-phenylpiperazin-1-yl)propan-1-amine is a chemical compound with the molecular formula C13H20N2. It is an amphetamine derivative that belongs to the class of psychoactive drugs known as substituted phenethylamines. The compound has a piperazine ring with a phenyl group attached, along with an amine and a propyl chain. This chemical has been studied for its potential use as a central nervous system stimulant and has been associated with psychoactive effects, including increased energy, alertness, and euphoria. However, it is also known to have potential for abuse and can be harmful if not used appropriately. Due to its psychoactive effects, 3-(4-phenylpiperazin-1-yl)propan-1-amine is considered a controlled substance in many countries.

InChI:InChI=1/C13H21N3/c14-7-4-8-15-9-11-16(12-10-15)13-5-2-1-3-6-13/h1-3,5-6H,4,7-12,14H2

Upstream product

• 18505-84-5 3-[4-(phenyl)-piperazin-1-yl]-propionitrile 
• 124-40-3 dimethyl amine 
• 92-54-6 4-phenyl-1-piperazine 
• 5460-29-7 2-(3-bromopropyl)isoindole-1,3-dione 
• 25557-30-6 2-[3-(4-penylpiperazin-1-yl)propyl]-1H-isoindole-1,3(2H)-dione 
• 5003-71-4 3-bromopropylamine hydrochloride 
• 4004-95-9 1-phenylpiperazine hydrochloride 
• 367275-35-2 [3-(4-phenylpiperazin-1-yl)propyl]carbamic acid benzyl ester 

Downstream Products

• 96064-03-8 N-[3-(4-phenyl-piperazin-1-yl)-propyl]-benzamide 
• 25557-43-1 3-hydroxy-2-[3-(4-phenyl-piperazin-1-yl)-propyl]-2,3-dihydro-isoindol-1-one 

Relevant articles and documents

Computer-Aided Search for 5-Arylideneimidazolone Anticancer Agents Able To Overcome ABCB1-Based Multidrug Resistance

ABCB1 modulation is an interesting strategy in the search for new anticancer agents that can overcome multidrug resistance (MDR). Hence, 17 new 5-arylideneimidazolones containing an amine moiety, as potential ABCB1 inhibitors, were designed, synthesized, and investigated. The series was tested in both parental (PAR) and multidrug-resistant (MDR) ABCB1-overexpressing T-lymphoma cancer cells using cytotoxicity assays. The ABCB1-modulating activity was examined in rhodamine 123 accumulation tests, followed by Pgp-Glo Assay to determine the influence of the most active compounds on ATPase activity. Lipophilic properties were assessed both, in silico and experimentally (RP-TLC). Pharmacophore-based molecular modelling toward ABCB1 modulation was performed. The studies allowed the identification of anticancer agents (p-fluorobenzylidene derivatives) more potent than doxorubicin, with highly selective action on MDR T-lymphoma cells (selectivity index >40). Most of the investigated compounds showed ABCB1-modulating action; in particular, two 5-benzyloxybenzylidene derivatives displayed activity nearly as strong as that of tariquidar.

Design, Synthesis, Structure-Activity Relationship Studies, and Three-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) Modeling of a Series of O-Biphenyl Carbamates as Dual Modulators of Dopamine D3 Receptor and Fatty Acid Amide Hydrolase

We recently reported molecules designed according to the multitarget-directed ligand paradigm to exert combined activity at human fatty acid amide hydrolase (FAAH) and dopamine receptor subtype D3 (D3R). Both targets are relevant for tackling several types of addiction (most notably nicotine addiction) and other compulsive behaviors. Here, we report an SAR exploration of a series of biphenyl-N-[4-[4-(2,3-substituted-phenyl)piperazine-1-yl]alkyl]carbamates, a novel class of molecules that had shown promising activities at the FAAH-D3R target combination in preliminary studies. We have rationalized the structural features conducive to activities at the main targets and investigated activities at two off-targets: dopamine receptor subtype D2 and endocannabinoid receptor CB1. To understand the unexpected affinity for the CB1 receptor, we devised a 3D-QSAR model, which we then prospectively validated. Compound 33 was selected for PK studies because it displayed balanced affinities for the main targets and clear selectivity over the two off-targets. 33 has good stability and oral bioavailability and can cross the blood-brain barrier.

PHENYL CARBAMATES AND THEIR USE AS INHIBITORS OF THE FATTY ACID AMIDE HYDROLASE (FAAH) ENZYME AND MODULATORS OF THE D3 DOPAMINE RECEPTOR (D3DR)

The invention provides compounds of Formula (I) or pharmaceutically acceptable salts thereof wherein Ar', R1, R2, R3, R4, X, Y are as defined in the description of invention, as multi-target directed ligands (MT