146-54-3 Usage
Description
Triflupromazine, also known by the brand name Vesprin, is a member of the phenothiazine class of compounds. It is characterized by a 10H-phenothiazine structure with a trifluoromethyl substituent at the 2-position and a 3-(dimethylamino)propyl group at the N-10 position. Triflupromazine is a potent antipsychotic agent that has been widely used in the treatment of various psychiatric disorders.
Uses
Used in Psychiatric Practice:
Triflupromazine is used as an antipsychotic agent for managing psychomotor excitement in patients with schizophrenia, particularly those exhibiting paranoid and manic-depressive conditions. It is also utilized in the treatment of neurosis, helping to alleviate symptoms and improve the overall mental health of patients.
Used in Schizophrenia Treatment:
In the treatment of schizophrenia, triflupromazine is used as an antipsychotic agent to help control the symptoms of the disorder. It works by stabilizing the mood and reducing the intensity of hallucinations and delusions, thereby improving the patient's overall quality of life.
Used in Manic-Depressive Conditions:
Triflupromazine is employed as a mood stabilizer for patients with manic-depressive conditions, also known as bipolar disorder. It helps to regulate the patient's mood swings and reduce the severity of both manic and depressive episodes.
Used in Neurosis Treatment:
For patients suffering from neurosis, triflupromazine is used as an anxiolytic and antipsychotic agent. It helps to alleviate anxiety, tension, and other symptoms associated with neurotic disorders, promoting a sense of calm and well-being.
Originator
Vesprin,Squibb,US,1957
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.
Therapeutic Function
Tranquilizer
Safety Profile
Poison 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.
Synthesis
Triflupromazine, 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].
Check Digit Verification of cas no
The CAS Registry Mumber 146-54-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 6 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 146-54:
(5*1)+(4*4)+(3*6)+(2*5)+(1*4)=53
53 % 10 = 3
So 146-54-3 is a valid CAS Registry Number.
InChI:InChI=1/C18H19F3N2S/c1-22(2)10-5-11-23-14-6-3-4-7-16(14)24-17-9-8-13(12-15(17)23)18(19,20)21/h3-4,6-9,12H,5,10-11H2,1-2H3
146-54-3Relevant articles and documents
A Focused Library of Psychotropic Analogues with Neuroprotective and Neuroregenerative Potential
Uliassi, Elisa,Pena-Altamira, Luis Emiliano,Morales, Aixa V.,Massenzio, Francesca,Petralla, Sabrina,Rossi, Michele,Roberti, Marinella,Martinez Gonzalez, Loreto,Martinez, Ana,Monti, Barbara,Bolognesi, Maria Laura
, p. 279 - 294 (2019)
Overcoming the lack of effective treatments and the continuous clinical trial failures in neurodegenerative drug discovery might require a shift from the prevailing paradigm targeting pathogenesis to the one targeting simultaneously neuroprotection and neuroregeneration. In the studies reported herein, we sought to identify small molecules that might exert neuroprotective and neuroregenerative potential as tools against neurodegenerative diseases. In doing so, we started from the reported neuroprotective/neuroregenerative mechanisms of psychotropic drugs featuring a tricyclic alkylamine scaffold. Thus, we designed a focused-chemical library of 36 entries aimed at exploring the structural requirements for efficient neuroprotective/neuroregenerative cellular activity, without the manifestation of toxicity. To this aim, we developed a synthetic protocol, which overcame the limited applicability of previously reported procedures. Next, we evaluated the synthesized compounds through a phenotypic screening pipeline, based on primary neuronal systems. Phenothiazine 2Bc showed improved neuroregenerative and neuroprotective properties with respect to reference drug desipramine (2Aa). Importantly, we have also shown that 2Bc outperformed currently available drugs in cell models of Alzheimer's and Parkinson's diseases and attenuates microglial activation by reducing iNOS expression.
Assembly of substituted phenothiazines by a sequentially controlled CuI/L-proline-catalyzed cascade C-S and C-N bond formation
Dawei, Ma.,Geng, Qian,Zhang, Hui,Jiang, Yongwen
supporting information; experimental part, p. 1291 - 1294 (2010/05/17)
(Chemical equation presented) In the pro-line of fire: A general and efficient cascade reaction approach to substituted phenothiazines, which relies on controlled sequential Cul/L-prolinecatalyzed C-S and C-N bond formations, is described. DMSO = dimethylsulfoxide.
