ChemicalBook--->CAS DataBase List--->1098-60-8

1098-60-8

1098-60-8 Structure

1098-60-8 Structure
IdentificationBack Directory
[Name]

TRIFLUPROMAZINE HYDROCHLORIDE
[CAS]

1098-60-8
[Synonyms]

Neoprin
Flumazin
Fluorofen
triflupromazineHCl
LABOTEST-BB LT00772332
Fluopromazine hydrochloride
trifluopromazinehydrochloride
TRIFLUPROMAZINE HYDROCHLORIDE
Triupromazine Hydrochloride (200 mg)
Triflupromazine Hydrochloride (200 mg)
TRIFLUPROMAZINE HYDROCHLORIDE VETRANAL,
TRIFLUPROMAZINE HYDROCHLORIDE USP/EP/BP
Triflupromazine Hydrochloride (1686003)
10-(3-dimethylaminopropyl)-2-(trifluoromethyl)phenothiazinehydrochloride
n,n-dimethyl-2-(trifluoromethyl)-10h-phenothiazine-10-propanaminmonohydr
10-(3-(dimethylamino)propyl)-2-(trifluoromethyl)-phenothiazinmonohydrochlo
10-[3-(Dimethylamino)-1-propyl]-2-(trifluoromethyl)phenothiazine Hydrochloride
2-(Trifluoromethyl)-10-[3-(dimethylamino)propyl]-10H-phenothiazine·hydrochloric acid
10H-Phenothiazine-10-propanamine, N,N-dimethyl-2-(trifluoromethyl)-, monohydrochloride
10H-Phenothiazine-10-propanamine,N,N-dimethyl-2-(trifluoromethyl)-, hydrochloride (1:1)
N,N-Dimethyl-3-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)propan-1-amine hydrochloride
[EINECS(EC#)]

214-149-6
[Molecular Formula]

C18H20ClF3N2S
[MDL Number]

MFCD00058103
[MOL File]

1098-60-8.mol
[Molecular Weight]

388.88
Hazard InformationBack Directory
[Chemical Properties]

White powder

[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.
[storage]

Store at -20°C
Chemical PropertiesBack Directory
[Melting point ]

174.0 to 179.0 °C
[storage temp. ]

Keep in dark place,Inert atmosphere,Room temperature
[solubility ]

DMF: 5mg/mL; DMSO: 3mg/mL; Ethanol: 5mg/mL; Ethanol:PBS (pH 7.2) (1:10): 0.09mg/mL
[Water Solubility ]

Soluble in water
[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 DataBack Directory
[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
Spectrum DetailBack Directory
[Spectrum Detail]

TRIFLUPROMAZINE HYDROCHLORIDE(1098-60-8)1HNMR
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