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HomeProduct name listTRIFLUPROMAZINE HYDROCHLORIDE

TRIFLUPROMAZINE HYDROCHLORIDE

Synonym(s):N,N-Dimethyl-2-(trifluoromethyl)-10H-phenothiazine-10-propanamine monohydrochloride

  • CAS NO.:1098-60-8
  • Empirical Formula: C18H20ClF3N2S
  • Molecular Weight: 388.88
  • MDL number: MFCD00058103
  • EINECS: 214-149-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 20:33:22
TRIFLUPROMAZINE HYDROCHLORIDE Structural

What is TRIFLUPROMAZINE HYDROCHLORIDE?

Description

Triflupromazine is a phenothiazine with diverse biological activities. It binds to muscarinic receptors in isolated rat corpus striatum (IC50 = 100 μM in a radioligand binding assay). Triflupromazine inhibits serotonin (5-HT) uptake by isolated rat brainstem synaptosomes (IC50 = 0.8 μM). It inhibits T. cruzi infection in mouse peritoneal macrophages when used at a concentration of 12.5 μM. Triflupromazine is active against S. aureus, shigellae, and vibrios (MICs = 2-100 μg/ml) in vitro and is protective against S. typhimurium infection in mice when administered at a dose of 30 μg per animal. Formulations containing triflupromazine were previously used as antipsychotics.

Originator

Vesprin,Squibb,US,1957

The Uses of TRIFLUPROMAZINE HYDROCHLORIDE

analgesic, antiinflammatory, antipyretic, COX-II inhibitor

What are the applications of Application

Triflupromazine hydrochloride is a neurology research compound

Manufacturing Process

Approximately 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 name

Vesprin (Bristol-Myers Squibb).

Therapeutic Function

Tranquilizer

General Description

Triflupromazinehydrochloride, 10-[3-(dimethylamino)propyl]-2-(trifluoromethyl)phenothiazine monohydrochloride (Vesprin), has agreater milligram potency as an antipsychotic, higher EPS,but lower sedative and hypotensive effects than chlorpromazine.The 2-CF3 versus the 2-Cl is associated with thesechanges. Overall, the drug has uses analogous to those ofchlorpromazine.

Properties of TRIFLUPROMAZINE HYDROCHLORIDE

Melting point: 174.0 to 179.0 °C
storage temp.  Keep in dark place,Inert atmosphere,Room temperature
Water Solubility  Soluble in water
solubility  DMF: 5mg/mL; DMSO: 3mg/mL; Ethanol: 5mg/mL; Ethanol:PBS (pH 7.2) (1:10): 0.09mg/mL
form  neat
color  White to Light yellow
λmax 305nm(H2O)(lit.)
Merck  14,9685
BRN  3801519
Stability: Hygroscopic
CAS DataBase Reference 1098-60-8

Safety information for TRIFLUPROMAZINE HYDROCHLORIDE

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H301:Acute toxicity,oral
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

Computed Descriptors for TRIFLUPROMAZINE HYDROCHLORIDE

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