Thioridazine

Thioridazine Basic information
Product Name:Thioridazine
Synonyms:THIORIDAZINE;10-[2-(1-Methyl-2-piperidyl)]-2-[methylthio] phenothiazine;THIORIDAZINE,1.0MG/MLINMETHANOL;10-[2-(1-ethyl-2-piperidyl)ethyl]-2-(methylthio)phenothiazine;10H-Phenothiazine, 10-[2-(1-methyl-2-piperidinyl)ethyl]-2-(methylthio)- (9CI);dl-Thioridazine;Phenothiazine, 10-[2-(1-methyl-2-piperidyl)ethyl]-2-(methylthio)- (6CI, 8CI);Thioril
CAS:50-52-2
MF:C21H26N2S2
MW:370.57
EINECS:200-044-2
Product Categories:Thioridazine
Mol File:50-52-2.mol
Thioridazine Structure
Thioridazine Chemical Properties
Melting point 72-74°
Boiling point bp0.02 230°
density 1.1693 (rough estimate)
refractive index 1.5800 (estimate)
Fp 9℃
storage temp. Sealed in dry,Room Temperature
solubility Practically insoluble in water, very soluble in methylene chloride, freely soluble in methanol, soluble in ethanol (96 per cent).
pka9.5(at 25℃)
form neat
Water Solubility 1.113mg/L(22.5 ºC)
NIST Chemistry Reference10H-Phenothiazine, 10-[2-(1-methyl-2-piperidyl)ethyl]-2-methylthio-(50-52-2)
Safety Information
Hazard Codes F,T
Risk 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
HS Code 2934302300
Hazardous Substances Data50-52-2(Hazardous Substances Data)
ToxicityLD50 orally in rats: 995 ±39 mg/kg (Goldenthal)
MSDS Information
Thioridazine Usage And Synthesis
DescriptionAn antipsychotic drug of the phenothiazine class. It is of particular interest because of its “atypical” properties, some of which may be due to its extensive bioconversion to active metabolites. The therapeutic and side effects of thioridazine and its metabolites involve blockade of brain dopamine receptors, but also actions mediated via blockage of muscarininc cholinergic and α-adrenergic receptors.
Chemical PropertiesColorless crystals. Soluble in water and alcohol.
OriginatorMellaril,Sandoz,US,1959
UsesMellaril(Novartis).
UsesIn terms of antipsychotic activity, thioridazine is inferior to aminazine. It is most effective in mental and emotional disorders accompanied by fear, stress, and excitement. It is prescribed for various forms of schizophrenia, psychosis, and neurosis.
DefinitionChEBI: A phenothiazine derivative having a methylsulfanyl subsitituent at the 2-position and a (1-methylpiperidin-2-yl)ethyl] group at the N-10 position.
Manufacturing ProcessN-(m-methylmercapto-phenyl)-aniline (MP 59° to 61°C) is prepared by condensing m-methylmercapto-aniline (BP 163° to 165°C/16 mm Hg) with the potassium salt of o-chloro-benzoic acid and decarboxylating the resultant N- (m-methylmercapto-phenyl)-anthranilic acid (MP 139° to 141°C) by heating, and then distilling.
9.87 parts of N-(m-methylmercapto-phenyl)-aniline are heated with 2.93 parts of sulfur and 0.15 part of powdered iodine for 15 minutes in a bath at about 160°C. Upon termination of the ensuing evolution of hydrogen sulfide, animal charcoal is added to the reaction mixture and recrystallization carried out first from 40 parts by volume of chlorobenzene, and then from 25 to 30 parts by volume of benzene at the boiling temperature. The obtained citronyellow 3-methylmercapto-phenothiazine has a MP of 138° to 140°C.
17.82 parts of 2-methylmercapto-phenothiazine, 3.4 parts of finely pulverized sodamide and 80 parts by volume of absolute xylene are heated to boiling for two hours at a bath temperature of 180°C under a reflux condenser and while stirring the reaction mixture. Without interrupting the heating, a solution of 13.2 parts of 2-(N-methyl-piperidyl-2')-1chloro-ethane in 40 parts by volume of absolute xylene is then added dropwise in the course of 1 1/2 hours. After further heating for 3 hours, the reaction mixture is cooled and, after the addition of 5 parts of ammonium chloride, is shaken three times with water, using 25 parts by volume each time. The xylene solution is extracted once with 35 parts by volume of 3 normal acetic acid and then three times, each time with 15 parts by volume of the said acid, after which the acetic acid extract is washed with 60 parts by volume of ether and is then made phenolphthalein-alkaline by means of 25 parts by volume of concentrated aqueous caustic soda solution.
The precipitated oily base is taken up in a total of 100 parts by volume of benzene. The benzene layer, dried over potassium carbonate, is filtered and then evaporated under reduced pressure. The residue from the evaporation is distilled in a high vacuum; after separating a preliminary distillate which passes over up to 228°C under a pressure of 0.92 mm Hg, the principal fraction, 2-methylmercapto-10-[2'-(N-methyl-piperidyl-2'')-ethyl- 1']phenothiazine, which distills over at 228° to 232°C under the lastmentioned pressure, is collected. The analytically pure base has a BP of 230°C/0.02 mm Hg.


Therapeutic FunctionTranquilizer
SynthesisThioridazine, 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].

Synthesis_50-52-2

Thioridazine Preparation Products And Raw materials
Thioridazine-d3 Hydrochloride Triacetonediamine THIORIDAZINE FOR SYSTEM SUITABILITY Methyl thioridazine N-oxide THIORIDAZINE - REFERENCE SPECTRUM Mesoridazine Besylate THIORIDAZINE /THIORIDAZINE HCL METHYL ETHYLCELLULOSE PIPERIDINE, 2-(2-CHLOROETHYL)-1-METHYL [THIORIDAZINE BASE] Thioridazine sulfoxide,thioridazine-5-sulfoxide Thioridazine chloridate,THIORIDAZINE HCL Thioridazine-D3HCl (R)-Thioridazine,(R)-(+)-Thioridazine ISOMETHIOZIN Kresoxim-methyl THIORIDAZINE HYDROCHLORIDE (S)-(-)-Thioridazine,(S)-Thioridazine

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