Thioridazine Chemical Properties

Melting point:

72-74°

Boiling point:

bp0.02 230°

Density 

1.1693 (rough estimate)

refractive index 

1.5800 (estimate)

Flash point:

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).

pka

9.5(at 25℃)

Water Solubility 

1.113mg/L(22.5 ºC)

NIST Chemistry Reference

10H-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 Data

50-52-2(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 995 ±39 mg/kg (Goldenthal)

Thioridazine Usage And Synthesis

Description

An 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 Properties

Colorless crystals. Soluble in water and alcohol.

Originator

Mellaril,Sandoz,US,1959

Uses

Mellaril(Novartis).

Uses

In 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.

Definition

ChEBI: 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 Process

N-(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 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].

Thioridazine(50-52-2)Related Product Information

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