84-97-9

Basic information

• Product Name: 10-[3-(4-methyl-1-piperazinyl)propyl]-10H-phenothiazine
• Synonyms: 10-[3-(4-methyl-1-piperazinyl)propyl]-10H-phenothiazine;Perazine;10-[3-[4-Methyl-1-piperazinyl] propyl] phenothiazine;10H-Phenothiazine, 10-(3-(4-methyl-1-piperazinyl)propyl)-, (Z)-2-buten edioate (1:2);10-[3-(4-Methylpiperazinyl)propyl]phenothiazine;NSC 638694;P 725;Pernazine
• CAS NO: 84-97-9
• Molecular Formula: C₂₀H₂₅N₃S
• Molecular Weight: 339.4976
• EINECS: 201-578-9
• Product Categories: Heterocyclic Compounds;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 84-97-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 51-53°C
• Boiling Point: bp0.001 160-170° (air bath temp)
• Flash Point: 252.3°C
• Appearance: /
• Density: 1.1341 (rough estimate)
• Vapor Pressure: 6.91E-10mmHg at 25°C
• Refractive Index: 1.5605 (estimate)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: 7.66±0.10(Predicted)
• CAS DataBase Reference: 10-[3-(4-methyl-1-piperazinyl)propyl]-10H-phenothiazine(CAS DataBase Reference)
• NIST Chemistry Reference: 10-[3-(4-methyl-1-piperazinyl)propyl]-10H-phenothiazine(84-97-9)
• EPA Substance Registry System: 10-[3-(4-methyl-1-piperazinyl)propyl]-10H-phenothiazine(84-97-9)

Safety Data

• Hazardous Substances Data: 84-97-9(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline Solid

Uses

Antipsychotic.

Definition

ChEBI: A phenothiazine derivative in which 10H-phenothiazinecarries a 3-(4-methylpiperazin-1-yl)propyl substituent at the N-10 position.

Safety Profile

Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion and subcutaneous routes. Human toxic effects by unspecified route. When heated to decomposition it emits very toxic fumes of NOx and SOx.

InChI:InChI=1/C20H25N3S/c1-21-13-15-22(16-14-21)11-6-12-23-17-7-2-4-9-19(17)24-20-10-5-3-8-18(20)23/h2-5,7-10H,6,11-16H2,1H3

Upstream product

• 109-01-3 1-methyl-piperazine 
• 92357-95-4 10-(3-bromopropyl)phenothiazine 
• 92-84-2 10H-phenothiazine 
• 3240-48-0 N-Desmethylperazine 
• 5909-59-1 10-(3-chloropropyl)-10H-phenothiazine 
• 362-04-9 methyl β-(10-phenothiazinyl)propionate 
• 89755-05-5 10H-phenothiazine-10-propanoyl chloride 
• 1698-80-2 10H-phenothiazine-10-propanenitrile 
• 102551-31-5 4-(3-phenothiazin-10-yl-propyl)-piperazine-1-carbodithioic acid 
• 104-16-5 3-(N-methylpiperazinyl)propyl chloride 
• 91508-47-3 β-(10-phenothiazinyl)propion-4-methylpiperazide 
• 95128-72-6 4-(3-phenothiazin-10-yl-propyl)-piperazine-1-carboxylic acid ethyl ester 

Downstream Products

• 6002-77-3 Perazine dimaleate 
• 90331-31-0 Perazin-1-methyl-4-benzyl-dichlorid 
• 90331-28-5 Perazin-4-methyliodid 
• 74167-55-8 Perazin-1,4-dimethyliodid 
• 90331-29-6 Perazin-4-benzylbromid 

Relevant articles and documents

Phenothiazine compound as well as preparation method and application thereof

The invention discloses a phenothiazine compound which has the advantages of novel structural general formula and framework, high efficiency, low toxicity and better inhibitory activity on LSD1. The invention also discloses a preparation method of the compound. The preparation method has the characteristics of mild reaction conditions, simplicity in operation and high reaction yield. According to the invention, phenothiazine is taken as a raw material, active groups are respectively introduced to a parent of phenothiazine, and new phenothiazine pharmacophores are synthesized; and phenothiazine compounds are designed and synthesized by modification with piperazine, morpholine, piperidine and other groups. The compound retains the activity of phenothiazine and also has the characteristics of modification groups, so that the biological activity of original molecules is improved, and the anti-tumor activity of target molecules is improved. The invention also discloses an application of the compound in preparation of LSD1-targeted antitumor drugs, and the compound shows good inhibitory activity on LSD1 and shows good development potential.

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.

Synthesis of Perazine

A novel synthesis of perazine (10-(4-methylpiperazinyl-3-propyl)phenothiazine), likely to be applicable to 10-dialkylaminopropyl phenothiazines generally, is described.