146561-59-3

Basic information

• Product Name: 3-(4-benzylpiperazin-1-yl)-1-cyclobutyl-1-hydroxy-1-phenylpropan-2-one
• Synonyms: 2-propanone, 1-cyclobutyl-1-hydroxy-1-phenyl-3-[4-(phenylmethyl)-1-piperazinyl]-; 3-(4-Benzylpiperazinyl)-1-cyclobutyl-1-hydroxy-1-phenyl-2-propanone
• CAS NO: 146561-59-3
• Molecular Formula: C₂₄H₃₀N₂O₂
• Molecular Weight: 378.5072
• Mol File: 146561-59-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 527.7°C at 760 mmHg
• Flash Point: 273°C
• Density: 1.18g/cm³
• Vapor Pressure: 5.77E-12mmHg at 25°C
• Refractive Index: 1.607
• CAS DataBase Reference: 3-(4-benzylpiperazin-1-yl)-1-cyclobutyl-1-hydroxy-1-phenylpropan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-benzylpiperazin-1-yl)-1-cyclobutyl-1-hydroxy-1-phenylpropan-2-one(146561-59-3)
• EPA Substance Registry System: 3-(4-benzylpiperazin-1-yl)-1-cyclobutyl-1-hydroxy-1-phenylpropan-2-one(146561-59-3)

Safety Data

• Hazardous Substances Data: 146561-59-3(Hazardous Substances Data)

Usage

Classification

Synthetic opioid derivative

Pharmacological action

Strong agonist at the μ-opioid receptor

Effects

Analgesia, sedation, euphoria

Risk factors

High potential for abuse and addiction, respiratory depression, overdose

Medical approval

Not approved for medical use

Legal status

Controlled as a Schedule I substance in many countries

Upstream product

• 135134-16-6 1-cyclobutyl-1-hydroxy-1-phenyl-2-propanone 
• 2759-28-6 1-phenylmethylpiperazine 
• 135134-17-7 3-bromo-1-cyclobutyl-1-hydroxy-1-phenyl-2-propanone 

Relevant articles and documents

Synthesis and antimuscarinic activity of some 1-cycloalkyl-1-hydroxy-1- phenyl-3-(4-substituted piperazinyl)-2-propanones and related compounds

A new class of substituted 1-phenyl-3-piperazinyl-2-propanones with antimuscarinic activity is reported. As part of a structure-activity relationship study of this class, various structural modifications, particularly ones involving substitution of position 1 and the terminal piperazine nitrogen, were investigated. The objective of this study was to derive new antimuscarinic agents with potential utility in treating urinary incontinence associated with bladder muscle instability. These compounds were examined for M1, M2, and M3 muscarinic receptor selectivity in isolated tissue assays and for in vivo effects on urinary bladder contraction, mydriasis, and salivation in guinea pigs. Potency and selectivity in these assays were influenced most notably by the nature of the substituent group on the terminal nitrogen of the piperazine moiety. Benzyl substitution was particularly advantageous in producing compounds with functional M3 receptor (smooth muscle) and bladder selectivity; it provided several candidates for clinical study. In vivo, 3-(4-benzylpiperazinyl)-1-cyclobutyl-1-hydroxy-1- phenyl-2-propanone (24) demonstrated 11- and 37-fold separations in its effect on bladder function versus mydriatic and salivation responses, respectively. The corresponding 2-chlorobenzyl derivative 25 was more than 178-fold selective for M3 versus M1 and M2 muscarinic receptors. 3-(4- Benzylpiperazinyl)-1,1-diphenyl-1-hydroxy-2-propanone (51) was 18-fold selective for M3 versus M1 and 242-fold selective for M3 versus M2 receptors. It was also selective in guinea pigs, where it displayed 20- and 41-fold separations between bladder function and effect on mydriasis and salivation, respectively. In general, the results of this study are consistent with the proposition that the described piperazinylpropanones interact with muscarinic receptors in a hydrogen-bonded form that presents a conformation similar to that apparently adopted by classical antimuscarinic agents.