| Identification | Back 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 Information | Back 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 | [References]
[1] SOLOMON H. SNYDER Henry I Y David Greenberg. Antischizophrenic drugs: Affinity for muscarinic cholinergic receptor sites in the brain predicts extrapyramidal effects[J]. Journal of psychiatric research, 1974, 11: Pages 91-95. DOI: 10.1016/0022-3956(74)90078-8
[2] TUOMISTO J. A new modification for studying 5-HT uptake by blood platelets: a re-evaluation of tricyclic antidepressants as uptake inhibitors*[J]. Journal of Pharmacy and Pharmacology, 1974, 26 2: 92-100. DOI: 10.1111/j.2042-7158.1974.tb09231.x
[3] S L DE CASTRO M de N D M M N Soeiro. Trypanosoma cruzi: effect of phenothiazines on the parasite and its interaction with host cells.[J]. Memorias do Instituto Oswaldo Cruz, 1992, 87 2: 209-215. DOI: 10.1590/s0074-02761992000200007
[4] S. DASTIDAR. Triflupromazine: a microbicide non-antibiotic compound.[J]. Acta microbiologica et immunologica Hungarica, 2004, 51 1-2 1: 75-83. DOI: 10.1556/amicr.51.2004.1-2.5 |
| Chemical Properties | Back 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 Data | Back 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 |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Spectrum Chemical Manufacturing Corp.
|
| Telephone: |
021-021-021-67601398-809-809-809 15221380277 |
| Website: |
www.spectrumchemical.com/oa_html/index.jsp?minisite=10020&respid=22372&language=us |
| Company Name: |
Cool Pharm, Ltd
|
| Telephone: |
021-60455363 18019463053 |
| Website: |
www.coolpharm.com |
|