50-52-2

Basic information

• Product Name: Thioridazine
• Synonyms: THIORIDAZINE;10-((1-methyl-2-piperidyl)ethyl)-2-(methylthio)-phenothiazin;10-(2-(1-methyl-2-piperidinyl)ethyl)-2-(methylthio)-10h-phenothiazin;10-(2-(1-methyl-2-piperidyl)ethyl)-2-(methylthio)-phenothiazin;10-(2-(1-Methyl-2-piperidyl)ethyl)-2-(methylthio)phenothiazine;10-[2-(1-Methyl-2-piperdiyl)ethyl]-2-(methylthio)phenothiazine;10-[2-(1-Methyl-2-piperidinyl)ethyl]-2-(methylsulfanyl)-10H-phenothiazine;10H-Phenothiazine, 10-[2-(1-methyl-2-piperidinyl)ethyl]-2-(methylthio)-
• CAS NO: 50-52-2
• Molecular Formula: C₂₁H₂₆N₂S₂
• Molecular Weight: 370.57
• EINECS: 200-044-2
• Product Categories: Thioridazine
• Mol File: 50-52-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 72-74°
• Boiling Point: bp0.02 230°
• Flash Point: 9℃
• Appearance: /
• Density: 1.1693 (rough estimate)
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: ?20°C
• Solubility: Practically insoluble in water, very soluble in methylene chloride, freely soluble in methanol, soluble in ethanol (96 per cent).
• PKA: 9.5(at 25℃)
• Water Solubility: 1.113mg/L(22.5 oC)
• CAS DataBase Reference: Thioridazine(CAS DataBase Reference)
• NIST Chemistry Reference: Thioridazine(50-52-2)
• EPA Substance Registry System: Thioridazine(50-52-2)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25-52/53
• Safety Statements: 16-36/37-45-61
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 1
• Hazardous Substances Data: 50-52-2(Hazardous Substances Data)

Usage

Description

Thioridazine, also known as Mellaril, is an antipsychotic drug belonging to the phenothiazine class. It is characterized by its "atypical" properties, which may be attributed to its extensive bioconversion to active metabolites. Thioridazine is a phenothiazine derivative with a methylsulfanyl substituent at the 2-position and a (1-methylpiperidin-2-yl)ethyl group at the N-10 position. It is known for its therapeutic and side effects involving the blockade of brain dopamine receptors, as well as actions mediated via blockage of muscarinic cholinergic and α-adrenergic receptors. Thioridazine is presented as colorless crystals and is soluble in water and alcohol.

Uses

Used in Pharmaceutical Industry:
Thioridazine is used as an antipsychotic agent for the treatment of various forms of schizophrenia, psychosis, and neurosis. It is particularly effective in addressing mental and emotional disorders accompanied by fear, stress, and excitement. However, it is considered inferior to aminazine in terms of antipsychotic activity.
In addition to its primary use as an antipsychotic medication, Thioridazine's chemical properties and solubility in water and alcohol may also make it suitable for other applications within the pharmaceutical industry, such as a component in the formulation of other drugs or as a research tool for studying the effects of phenothiazine derivatives on the central nervous system.

Therapeutic Function

Tranquilizer

Synthesis

Thioridazine, 10-[2-(1-methyl-2-piperidyl)ethyl]-2-(methylthio)phenothiazine (6.1.9), is synthesized in an analogous manner by alkylating 2-methylthiophenothiazine with 2-(2-chloroethyl)-1-methylpiperidine [29,30].

InChI:InChI=1/C21H26N2S2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(24-2)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3

Upstream product

• 129846-85-1 N-(2-(1-methyl-2-piperidynyl)ethyl)-2-(2-fluorophenylthio)-5-(methylthio)aniline 
• 99970-41-9 10H-phenothiazine-2-thiol 
• 1783-81-9 3-methylmercaptoaniline 
• 16463-38-0 potassium 2-chlorobenzoate 
• 18902-93-7 N-(3'-methylthiophenyl)anthranylic acid 
• 101895-74-3 2-benzylsulfanyl-10H-phenothiazine 
• 13313-45-6 N-(3-methylthiophenyl)phenylamine 
• 7643-08-5 2-(methylthio)-10H-phenothiazine 
• 32672-69-8 mesoridazine besylate 
• 129846-82-8 2-(2-fluorophenylthio)-5-(methylthio)nitrobenzene 
• 129846-83-9 2-(2-fluorophenylthio)-5-(methylthio)aniline 
• 2557-78-0 2-fluorothiophenol 
• 1199-36-6 1-chloro-4-(methylthio)-2-nitrobenzene 

Downstream Products

• 10538-32-6 Northioridazine 
• 130-61-0 thioridazine Hydrochloride 
• 14759-06-9 sulforidazine 
• 7776-05-8 Thioridazine 5-sulfoxide 
• 5588-33-0 mesoridazine 
• 103827-30-1 N-Oxide thioridazine 

Relevant articles and documents

Combination of experimental and in silico methods for the assessment of the phototransformation products of the antipsychotic drug/metabolite Mesoridazine

The lack of studies on the fate and effects of drug metabolites in the environment is of concern. As their parent compounds, metabolites enter the aquatic environment and are subject to biotic and abiotic process. In this regard, photolysis plays an important role. This study combined experimental and in silico quantitative structure-activity relationship (QSAR) methods to assess the fate and effects of Mesoridazine (MESO), a pharmacologically active human drug and metabolite of the antipsychotic agent Thioridazine, and its transformation products (TPs) formed through a Xenon lamp irradiation. After 256 min, the photodegradation of MESO ? besylate (50 mg L? 1) achieved 90.4% and 6.9% of primary elimination and mineralization, respectively. The photon flux emitted by the lamp (200–600 nm) was 169.55 J cm? 2. Sixteen TPs were detected by means of liquid chromatography-high resolution mass spectrometry (LC-HRMS), and the structures were proposed based on MSn fragmentation patterns. The main transformation reactions were sulfoxidation, hydroxylation, dehydrogenation, and sulfoxide elimination. A back-transformation of MESO to Thioridazine was evidenced. Aerobic biodegradation tests (OECD 301 D and 301F) were applied to MESO and the mixture of TPs present after 256 min of photolysis. Most of TPs were not biodegraded, demonstrating their tendency to persist in aquatic environments. The ecotoxicity towards Vibrio fischeri showed a decrease in toxicity during the photolysis process. The in silico QSAR tools QSARINS and US-EPA PBT profiler were applied for the screening of TPs with character of persistence, bioaccumulation, and toxicity (PBT). They have revealed the carbazole derivatives TP 355 and TP 337 as PBT/vPvB (very persistent and very bioaccumulative) compounds. In silico QSAR predictions for mutagenicity and genotoxicity provided by CASE Ultra and Leadscope indicated positive alerts for mutagenicity on TP 355 and TP 337. Further studies regarding the carbazole derivative TPs should be considered to confirm their hazardous character.

Anti-proliferative drugs

The present invention relates to methods for the treatment of diseases associated with hyper-proliferation of cells by administering to a subject in need a therapeutically effective amount of at least one psychotropic agent. Specific proliferative diseases against which psychotropic agents were found to be effective are cancer, including multi-drug resistant cancer and diseases associated with hyper-proliferation of the skin cells, such as psoriasis and hyperkeratosis.

Stability of some phenothiazine free radicals.

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