1033-68-7

Basic information

• Product Name: 1-Phenethyl-4-phenylpiperazine
• Synonyms: 1-Phenethyl-4-phenylpiperazine
• CAS NO: 1033-68-7
• Molecular Formula: C₁₈H₂₂N₂
• Molecular Weight: 266.3807
• Mol File: 1033-68-7.mol
• Article Data: 8

Chemical Properties

• Melting Point: 77-78 °C
• Boiling Point: 397°Cat760mmHg
• Flash Point: 177.5°C
• Appearance: /
• Density: 1.061g/cm³
• Vapor Pressure: 1.63E-06mmHg at 25°C
• Refractive Index: 1.582
• PKA: 7.51±0.10(Predicted)
• CAS DataBase Reference: 1-Phenethyl-4-phenylpiperazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Phenethyl-4-phenylpiperazine(1033-68-7)
• EPA Substance Registry System: 1-Phenethyl-4-phenylpiperazine(1033-68-7)

Safety Data

• Hazardous Substances Data: 1033-68-7(Hazardous Substances Data)

Usage

General Description

1-Phenethyl-4-phenylpiperazine is a chemical compound that belongs to the class of piperazines, which are often used in the pharmaceutical industry. It is a psychoactive drug that acts as a stimulant and has been studied for its potential use in treating depression and anxiety. 1-Phenethyl-4-phenylpiperazine has also been identified as a designer drug and has been found in some illicit substances. It is known to have a similar structure to other psychoactive compounds and may have similar effects on the central nervous system, although its specific mechanisms of action are not fully understood. 1-Phenethyl-4-phenylpiperazine is considered a controlled substance in some countries due to its potential for abuse and its psychoactive effects. Research on this compound continues to explore its potential therapeutic uses and its potential risks to public health.

InChI:InChI=1/C18H22N2/c1-3-7-17(8-4-1)11-12-19-13-15-20(16-14-19)18-9-5-2-6-10-18/h1-10H,11-16H2

Upstream product

• 92-54-6 4-phenyl-1-piperazine 
• 103-63-9 1-phenyl-2-bromoethane 
• 100-42-5 styrene 
• 60-12-8 2-phenylethanol 
• 20020-27-3 2-phenylethyl mesylate 
• 50-00-0 formaldehyd 
• 62673-31-8 benzyl(bromo)zinc 
• 622-24-2 2-phenylethyl chloride 

Relevant articles and documents

Ru-catalyzed β-selective and enantioselective addition of amines to styrenes initiated by direct arene-exchange

A catalytic β-selective addition of amines to styrenes proceeded in the presence of cationic Ru complexes combined with diphosphine ligands. In the reaction of α-methylstyrene, an enantioselective addition was achieved by using xylylBINAP.

Straightforward three-component synthesis of diarylmethylpiperazines and 1,2-diarylethylpiperazines

Several functionalized diarylmethylpiperazines and 1,2-diarylethylpiperazines have been synthesized in moderate to high yield according to a one-step three-component coupling between an aromatic or a benzylic organozinc reagent, a piperazine derivative, and an aromatic aldehyde. The procedure can be extended to the synthesis of benzylpiperazine derivatives or β-arylethylpiperazines toward the use of paraformaldehyde or aliphatic aldehydes.

Interaction of arylpiperazines with the dopamine receptor D2 binding site

The docking of several 1-benzyl-4-arylpiperazines to the dopamine receptor (DAR) D2 was examined. The results demonstrated that the interaction of protonated N1 of the piperazine ring with Asp 86 (III.32) and edge-to-face interactions of the aromatic ring of the arylpiperazine part of the ligand with Phe 178 (VI.44), Trp 182 (VI.48) and Tyr 216 (VII.58) of the receptor, represent the major stabilizing forces. Besides, the hydrogen bond acceptor group in position 2 of the phenylpiperazine aromatic ring could build one more hydrogen bond with Trp 182 (VI.48). Bulky substituents in position 4 were not tolerated due to the unfavorable sterical interaction with Phe 178 (VI.44). Substituents in position 2 and 3 were found to be sterically well tolerated. Introduction of electron attractive -NO2 group in position 3 of arylpiperazines decreased, while electron donors (-OMe) and the second aromatic ring (naphthyl) increased the binding affinity comparing to that of the phenylpiperazine 1. This can be explained in terms of favoured edge-to-face interactions in ligands with a high negative electrostatic surface potential (ESP) in the centre of aromatic residue of arylpiperazines. Thus, besides the salt bridges and hydrogen bonds, edge-to-face interactions significantly contribute to arylpiperazine ligands to form complexes with the DAR D2. Phe 178 (VI.44), Trp 182 (VI.48) and Tyr 216 (VII.58) can be considered as a part of the ancillary DAR D2 pocket preserved in most G protein-coupled receptors of the A class and obviously, the arylpiperazine structural motif represents one of the privileged structures that bind to this pocket.