TRIFLUPROMAZINE HYDROCHLORIDE Property

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

color 

White to Light yellow

λmax

305nm(H2O)(lit.)

Merck 

14,9685

BRN 

3801519

Stability:

Hygroscopic

CAS DataBase Reference

1098-60-8

Safety

Hazard Codes 

Xn

Risk Statements 

20/21/22

Safety Statements 

36

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

SO8925000

HazardClass 

6.1

PackingGroup 

III

HS Code 

2934302300

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

TRIFLUPROMAZINE HYDROCHLORIDE Chemical Properties,Usage,Production

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

Uses

analgesic, antiinflammatory, antipyretic, COX-II inhibitor

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.