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Trifluoperazine

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  • Trifluoperazine
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  • 2023-09-04
  • CAS:117-89-5
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  • Trifluoperazine
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  • 2021-08-20
  • CAS:117-89-5
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  • Purity: 99%
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Trifluoperazine Basic information
Product Name:Trifluoperazine
Synonyms:Trifluoperazine (base and/or unspecified salts);TRIFLUOPERAZINE;10-[3-(4-Methylpiperazin-1-yl)propyl]-2-trifluoromethyl-10H-phenothiazine;10-(3-(4-methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)-phenothiazin;10-(3-(4-Methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)phenothiazine;10-(gamma-(n’-methylpiperazino)propyl)-2-trifluoromethylphenothiazine;10-(gamma-(n’-methylpiperazino)propyl)-2-trifluoromethylphenothiozine;10-(gamma-(N'-Methylpiperazino)propyl)-2-trifluoromethylphenothiozine
CAS:117-89-5
MF:C21H24F3N3S
MW:407.5
EINECS:204-219-4
Product Categories:Organics
Mol File:117-89-5.mol
Trifluoperazine Structure
Trifluoperazine Chemical Properties
Melting point 232°C
Boiling point bp0.6 202-210°
density 1.2060 (estimate)
storage temp. Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility DMSO (Slightly), Methanol (Slightly), Water (Slightly)
form Solid
pkapKa 8.05±0.04(H2O t = 20 0.5 I not reported but pKa was stated to be independent of I.) (Uncertain)
color White to Off-White
Water Solubility 12.23mg/L(24 ºC)
NIST Chemistry ReferenceTrifluoperazine(117-89-5)
Safety Information
Hazardous Substances Data117-89-5(Hazardous Substances Data)
ToxicityLD50 orally in rats, mice: 542.7, 424.0 mg/ml (Fowler)
MSDS Information
Trifluoperazine Usage And Synthesis
OriginatorStelazine,SKF,US,1958
Uses10-[3-(4-Methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine is a psychoactive drug.
UsesAntipsychotic.
UsesTrifluoperazine is one of the most active antipsychotic drugs. A moderate stimulatory effect accompanies the neuroleptic effect. Trifluoperazine is unique in that, patients instead of the usual stiffness and weakness characteristic of phenothazine derivatives, become more lively. This drug has a strong anticonvulsant activity. It is widely used in psychiatry for treating schizophrenia and other mental illnesses.
DefinitionChEBI: Trifluoperazine is a member of the class of phenothiazines that is phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-(4-methylpiperazin-1-yl)propyl group at the N-10 position. It has a role as a dopaminergic antagonist, an antiemetic, an EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor, an EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor, a calmodulin antagonist and a phenothiazine antipsychotic drug. It is a N-alkylpiperazine, a N-methylpiperazine, a member of phenothiazines and an organofluorine compound.
Manufacturing ProcessA mixture of 17.2 grams of 2-trifluoromethylphenothiazine, 3.1 grams of sodamide and 14 grams of 1-(3'-chloropropyl)-4-methylpiperazine in 200 ml of xylene is heated at reflux for 2 hours. The salts are extracted into 150 ml of water. The xylene layer is then extracted with several portions of dilute hydrochloric acid. The acid extracts are combined and neutralized with ammonium hydroxide solution. The product, 10-[3'-(4''-methyl-1''- piperazinyl)-propyl]-2-trifluoromethylphenothiazine, is taken into benzene and purified by vacuum distillation, BP 202° to 210°C at 0.6 mm.
Therapeutic FunctionTranquilizer
Clinical Use
Schizophrenia and other psychoses
Anxiety
Severe nausea and vomiting
SynthesisTrifluoperazine, 2-trifluoromethyl-10-[3-(4-methyl-1-piperazinyl) propyl]- phenothazine (6.1.5), is synthesized in the manner described above of alkylation using 2- trifluoromethylphenothazin-4-methyl-1-piperazinylpropylchloride [11,17–20].
Drug interactionsPotentially hazardous interactions with other drugs
Anaesthetics: enhanced hypotensive effect.
Analgesics: increased risk of convulsions with tramadol; enhanced hypotensive and sedative effects with opioids; increased risk of ventricular arrhythmias with methadone.
Anti-arrhythmics: increased risk of ventricular arrhythmias with anti-arrhythmics that prolong the QT interval, e.g. procainamide, disopyramide, dronedarone and amiodarone - avoid with amiodarone and dronedarone.
Antibacterials: increased risk of ventricular arrhythmias with delamanid and moxifloxacin - avoid with moxifloxacin.
Antidepressants: increased level of tricyclics; possibly increased risk of antimuscarinic side effects; risk of ventricular arrhythmias with citalopram and escitalopram - avoid; possible increased risk of convulsions with vortioxetine.
Antiepileptics: antagonism (convulsive threshold lowered).
Antimalarials: avoid with artemether/lumefantrine and piperaquine with artenimol.
Antipsychotics: increased risk of ventricular arrhythmias with droperidol and pimozide - avoid; possible increased risk of ventricular arrhythmias with risperidone.
Antivirals: concentration possibly increased with ritonavir; increased risk of ventricular arrhythmias with saquinavir - avoid.
Anxiolytics and hypnotics: increased sedative effects.
Atomoxetine: increased risk of ventricular arrhythmias.
Beta-blockers: enhanced hypotensive effect; increased risk of ventricular arrhythmias with sotalol.
Cytotoxics: increased risk of ventricular arrhythmias with arsenic trioxide.
Diuretics: enhanced hypotensive effect.
Lithium: increased risk of extrapyramidal side effects and possibly neurotoxicity.
Pentamidine: increased risk of ventricular arrhythmias.
MetabolismTrifluoperazine undergoes extensive first pass metabolism. The major metabolite is the possibly active N-oxide; other metabolites include the sulfoxide and the 7-hydroxy derivative.
Elimination occurs in the bile and urine.
Tag:Trifluoperazine(117-89-5) Related Product Information
3-Methyl-2-butanone 1-Methylpiperazine Propyl butyrate Chloromethyl isopropyl carbonate Propyl gallate Cyclopropyl methyl ketone Isopropyl alcohol Phenothiazine Oxaflumazine Ciclofenazine FLUPHENAZINE Fluphenazine decanoate Trifluoperazine dihydrochloride FLUPHENAZINE HYDROCHLORIDE 2-(Trifluoromethyl)phenothiazine FLUPHENAZINE N-MUSTARD DIHYDROCHLORIDE Trifluoperazine-D3 Dihydrochloride fluphenazine O-enantate