653-03-2

Basic information

• Product Name: butaperazine
• Synonyms: butaperazine;1-[10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazin-2-yl]butan-1-one;1-[10-[3-(4-Methyl-1-piperazinyl)propyl]-10H-phenothiazin-2-yl]-1-butanone;AHR-712;Bayer-1362;Riker-595
• CAS NO: 653-03-2
• Molecular Formula: C₂₄H₃₁N₃OS
• Molecular Weight: 409.59
• EINECS: 211-493-9
• Mol File: 653-03-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: bp0.05 270-280°
• Appearance: /
• CAS DataBase Reference: butaperazine(CAS DataBase Reference)
• NIST Chemistry Reference: butaperazine(653-03-2)
• EPA Substance Registry System: butaperazine(653-03-2)

Safety Data

• Hazardous Substances Data: 653-03-2(Hazardous Substances Data)

Usage

Originator

Bayer 1362,Bayer

Uses

Antipsychotic.

Manufacturing Process

To a suspension of sodamide in liquid ammonia is added of 2- buterylphenothiazine. After stirring for one hour, there is added 1-bromo-3- chloropropane. The ammonia is allowed to evaporate and the residue is diluted with the water. The mixture is extracted with ether and the ether solution is dried over anhydrous sodium sulfate, filtered and concentrated. The residue consists of crude 10-(3-chloropropyl)-2-buterylphenothiazine as viscous oil and is used in the next step without further purification. A mixture of 1-methylpiperazine and crude 10-(3-chloropropyl)-2- buterylphenothiazine is heated on a steam bath for 18 hours. The mixture is diluted with the water and extracted with ether. The ether solution is extracted with dilute hydrochloric acid. The aqueous acid solution is made alkaline with sodium hydroxide and the product is extracted with ether. The ether extracts are dried and concentrated to a residue consisting of the free base 2-butyryl-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazine.

InChI:InChI=1S/C24H31N3OS/c1-3-7-22(28)19-10-11-24-21(18-19)27(20-8-4-5-9-23(20)29-24)13-6-12-26-16-14-25(2)15-17-26/h4-5,8-11,18H,3,6-7,12-17H2,1-2H3

Upstream product

• 109-01-3 1-methyl-piperazine 

Downstream Products

• 1063-55-4 Butaperazindibimaleinat 

Relevant articles and documents

Synthesis and biochemical characterization of new phenothiazines and related drugs as MDR reversal agents

Chemotherapy is one of the most important methods in the treatment of cancer. However, development of drug resistance during chemotherapy is the leading cause of treatment failure and decreased survival in cancer patients. Multidrug resistance (MDR) is one of the extensively studied forms of drug resistance for more than 30 years. The members of ATP-binding cassette protein family are responsible for multidrug resistance with P-glycoprotein as most representative transporter. To overcome multidrug resistance, pharmacological modulation of the transporters by efflux pump inhibitors seem to be the first choice, but preclinical studies did not lead to clinical applications. Therefore, a systematical research for pharmacophor structures is a promising strategy to increase the efficacy of those drugs still influencing multidrug resistance. In this study a range of phenothiazine derivatives was synthesizied with systematical variation of three molecule domains. The biochemical determination of multidrug resistance reversal activity was achieved with the crystalviolet assay on LLC-PK1/MDR1 cells. The results will be discussed considering of hypotheses in the literature directed to new structure-acitivity relationships to overcome drug resistance in the future.