triflupromazine

triflupromazine Basic information
Product Name:triflupromazine
Synonyms:dimethyl(3-(2-trifluoromethylphenothiazin-10-yl)propyl)amine;fluopromazine;triflupromazine;TRIFLUOROPROMAZINE;10-[3-(Dimethylamino)propyl]-2-(trifluoromethyl)-10H-phenothiazine;Trifluopromazine;Vetame;N,N-dimethyl-3-[2-(trifluoromethyl)phenothiazin-10-yl]propan-1-amine
CAS:146-54-3
MF:C18H19F3N2S
MW:352.4170696
EINECS:2056736
Product Categories:
Mol File:146-54-3.mol
triflupromazine Structure
triflupromazine Chemical Properties
Melting point 25°C
Boiling point bp0.7 176°; bp0.4 162-164°
density 1.2198 (estimate)
refractive index nD23 1.5780
pkapKa 9.41(H2O (extrap) t = 24±1 I~0.002) (Uncertain)
Water Solubility 1.762mg/L(24 ºC)
Safety Information
Hazardous Substances Data146-54-3(Hazardous Substances Data)
MSDS Information
triflupromazine Usage And Synthesis
OriginatorVesprin,Squibb,US,1957
UsesIn psychiatric practice, triflupromazine is used for psychomotor excitement in patients with schizophrenia for paranoid and manic-depressive conditions, and for neurosis.
UsesAntipsychotic.
DefinitionChEBI: A member of the class of phenothiazines that is 10H-phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-(dimethylamino)propyl group at the N-10 position.
Manufacturing ProcessApproximately 3.8 grams of sodamide is freshly prepared from 2.25 grams of sodium, 90 grams of liquid ammonia and a catalytic trace of ferric nitrate. The ammonia is allowed to evaporate. A solution of 19.1 grams of 2-trifluoromethylphenothiazine (prepared by the Bernthsen thionation of 3- trifluoromethyldiphenylamine) in 160 ml of dry benzene is added to the reaction flask followed by 18 grams of 3-chloro-1-dimethylaminopropane. The reaction mixture is heated at reflux for 20 hours. After washing the cooled mixture with 130 ml of water, the organic layer is extracted with several portions of dilute hydrochloric acid. The acid extracts are combined and neutralized with ammonium hydroxide solution. The oily free base is extracted into benzene and purified by distillation to give 19.6 grams of 10-(3'- dimethylaminopropyl)-2-trifluoromethylphenothiazine, boiling point 177° to 181°C at 1 mm. The free base (7 grams) is converted to the hydrochloride salt by reacting an alcoholic solution of the base with hydrogen chloride gas.
Evaporation of the volatiles in vacuo leaves an amorphous solid which is recrystallized from ethanol/ether to pink crystals, MP 173° to 174°C, the hydrochloride salt of the free base prepared above.
Brand nameVesprin (Apothecon).
Therapeutic FunctionTranquilizer
Safety ProfilePoison by ingestion, intravenous, and intraperitoneal routes. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of F-, NOx, and SOx. See also FLUORIDES.
SynthesisTriflupromazine, 2-trifluoromethyl-10-(3-dimethylaminopropyl) phenothiazine (6.1.3), also is synthesized by the alkylation of 2-trifluoromethylphenothiazine using 3-dimethylaminopropylchloride in the presence of sodium amide [7–12].
triflupromazine Preparation Products And Raw materials
Raw materialsSodium amide-->2-(Trifluoromethyl)phenothiazine
Fluphenazine decanoate Trifluoperazine dihydrochloride TRIFLUPROMAZINE HYDROCHLORIDE Ciclofenazine Fluacizine fluphenazine O-enantate FLUPHENAZINE HYDROCHLORIDE FLUPHENAZINE DIMALEATE SALT Ftorpropazine FLUPHENAZINE N-MUSTARD DIHYDROCHLORIDE Homofenazine Trifluomeprazine FLUPHENAZINE Duoperone Oxaflumazine AZAFTOZINE Trifluoperazine triflupromazine

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