5588-33-0

Basic information

• Product Name: mesoridazine
• Synonyms: 10-[2-(1-methyl-2-piperidyl)ethyl]-2-methylsulfinyl-phenothiazine;10-[2-(1-methylpiperidin-2-yl)ethyl]-2-methylsulfinylphenothiazine;10-[2-(1-methylpiperidin-2-yl)ethyl]-2-methylsulfinyl-phenothiazine;10-[2-(1-Methyl-2-piperidinyl)ethyl]-2-(Methylsulfinyl)-phenothiazine;1-Methyl-2-[2-[2-(Methylsulfinyl)phenothiazin-10-yl]ethyl]piperidine;NSC 186066;Thioridazine-2-sulfoxide;TPS 23
• CAS NO: 5588-33-0
• Molecular Formula: C21H26N2OS2
• Molecular Weight: 386.581
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 5588-33-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 128-131 °C
• Boiling Point: 570.5°Cat760mmHg
• Flash Point: 298.9°C
• Appearance: /
• Density: 1.1234 (rough estimate)
• Vapor Pressure: 4.99E-13mmHg at 25°C
• Refractive Index: 1.5950 (estimate)
• PKA: 9.84±0.10(Predicted)
• CAS DataBase Reference: mesoridazine(CAS DataBase Reference)
• NIST Chemistry Reference: mesoridazine(5588-33-0)
• EPA Substance Registry System: mesoridazine(5588-33-0)

Safety Data

• Hazardous Substances Data: 5588-33-0(Hazardous Substances Data)

Usage

Chemical Properties

Pale Pink Solid

Uses

Different sources of media describe the Uses of 5588-33-0 differently. You can refer to the following data:
1. Mesoridazine (Thioridazine EP Impurity B) is an antipsychotic.
2. Mesoridazine is an antipsychotic.

Definition

ChEBI: A phenothiazine substituted at position 2 (para to the S atom) by a methylsulfinyl group, and on the nitrogen by a 2-(1-methylpiperidin-2-yl)ethyl group.

Therapeutic Function

Tranquilizer

InChI:InChI=1/C21H26N2OS2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(26(2)24)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3

Upstream product

• 50-52-2 thioridazine 

Downstream Products

• 14759-06-9 sulforidazine 
• 145823-24-1 1-((2R,3R,4S,5S,6S)-6-Carboxy-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-2-[2-(2-methanesulfinyl-phenothiazin-10-yl)-ethyl]-1-methyl-piperidinium; chloride 

Relevant articles and documents

Facile syntheses of the three major metabolites of thioridazine

Efficient, mild syntheses of the three major metabolites 2-4 of the important antipsychotic drug thioridazine (1) have been developed. The cardiotoxic metabolite 2 with a ring sulfoxide moiety was prepared in 96% yield by oxidation of 1 with NaIO4 under acidic conditions. Four different procedures were elaborated for the selective side-chain sulfide oxidation of 1 to mesoridazine (3), giving rise to yields of up to 91%. Finally, sulforidazine (4) was synthesised via oxidation of the sulfoxide 3 in the presence of either KMnO4 or t-BuOOH under basic conditions. Except for the oxidation with t-BuOOH. all reactions took place under mild conditions within a few minutes, were nicely reproducible, and afforded medium-to-high yields of the desired products, which could be readily purified by column chromatography.

Stability of some phenothiazine free radicals.

-