Trifluoperazine

Base Information

• Chemical Name: Trifluoperazine
• CAS No.: 117-89-5
• Molecular Formula: C21H24 F3 N3 S
• Molecular Weight: 407.503
• Hs Code.: 2934300000
• European Community (EC) Number: 204-219-4
• UNII: 214IZI85K3
• DSSTox Substance ID: DTXSID1046928
• Nikkaji Number: J5.293K
• Wikipedia: Trifluoperazine
• Wikidata: Q1752915
• NCI Thesaurus Code: C62084
• RXCUI: 10800
• Pharos Ligand ID: 11XN832CV5S1
• Metabolomics Workbench ID: 43119
• ChEMBL ID: CHEMBL422
• Mol file: 117-89-5.mol

Synonyms:Apo Trifluoperazine;Apo-Trifluoperazine;ApoTrifluoperazine;Eskazine;Flupazine;Stelazine;Terfluzine;Trifluoperazine;Trifluoperazine HCL;Trifluoperazine Hydrochloride;Trifluoroperazine;Trifluperazine;Triftazin

Chemical Property of Trifluoperazine

Chemical Property:

• Appearance/Colour: white to yellowish crystalline powder
• Vapor Pressure: 2.32E-10mmHg at 25°C
• Boiling Point: 506°Cat760mmHg
• PKA: pKa 8.05±0.04(H2O t = 20 0.5 I not reported but pKa was stated to be independent of I.) (Uncertain)
• Flash Point: 259.8°C
• PSA: 35.02000
• Density: 1.239g/cm³
• LogP: 4.88640
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Water Solubility.: 12.23mg/L(24 oC)
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 407.16430344
• Heavy Atom Count: 28
• Complexity: 510

Purity/Quality:

98%,99%, ^*data from raw suppliers

10-[3-(4-Methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): UN NO.
• Hazard Codes: UN NO.

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antipsychotic Agents
• Canonical SMILES: CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)C(F)(F)F
• Recent ClinicalTrials: The Use of Trifluoperazine in Transfusion Dependent DBA
• Recent EU Clinical Trials: Randomized multicentric open-label phase III clinical trial to evaluate the efficacy of continual treatment versus discontinuation based in the presence of prodromes in a first episode of non-affective psychosis.
• Uses: Antipsychotic. 10-[3-(4-Methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine is a psychoactive drug. Trifluoperazine 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.
• Therapeutic Function: Tranquilizer
• Clinical Use: Schizophrenia and other psychoses Anxiety Severe nausea and vomiting
• Drug interactions: Potentially 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.

Technology Process of Trifluoperazine

There total 5 articles about Trifluoperazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

1-methyl-piperazine (109-01-3) + 10-(3-iodopropyl)-2-(trifluoromethyl)-10H-phenothiazine (939382-31-7) → Trifluoperazine (117-89-5)

Guidance literature:

With potassium phosphate; In N,N-dimethyl-formamide; at 80 ℃; for 2h;

DOI:10.1016/j.bmcl.2007.03.064

Reference yield:

2-(trifluoromethyl)-10H-phenothiazine (92-30-8) → Trifluoperazine (117-89-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide / 2 h / 80 °C

1.2: NaI / acetone / 48 h / Heating

2.1: K₃PO₄ / dimethylformamide / 2 h / 80 °C

With potassium phosphate; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2007.03.064

Reference yield:

C21H24F3N3S(1+) → Trifluoperazine (117-89-5) + trifluoroperazine sulfoxide (1549-88-8)

Guidance literature:

With water; In sulfuric acid; at 24.84 ℃; Concentration; pH-value; Kinetics;

DOI:10.1007/s11243-011-9531-x

upstream raw materials:

1-methyl-piperazine

10-(3-iodopropyl)-2-(trifluoromethyl)-10H-phenothiazine

2-(trifluoromethyl)-10H-phenothiazine

Downstream raw materials:

1,4-bis-(2-hydroxyimino-2-phenyl-ethyl)-1-methyl-4-[3-(2-trifluoromethyl-phenothiazin-10-yl)-propyl]-piperazinediium; dibromide

1-((2R,3R,4S,5S,6S)-6-Carboxy-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-1-methyl-4-[3-(2-trifluoromethyl-phenothiazin-10-yl)-propyl]-piperazin-1-ium; chloride

Trifluoperazin-4-methyliodid

Trifluoperazin-1,4-dimethyliodid

Refernces

• 1、 Craig et al.. "-". . p. 709. Retrieved 1957.
• 2、 Madrid, Peter B.,Polgar, Willma E.,Toll, Lawrence,Tanga, Mary J.. "Synthesis and antitubercular activity of phenothiazines with reduced binding to dopamine and serotonin receptors". . p. 3014 - 3017. Retrieved 2008/02/07.