Thioridazine

Base Information

• Chemical Name: Thioridazine
• CAS No.: 50-52-2
• Deprecated CAS: 57129-06-3
• Molecular Formula: C21H26N2S2
• Molecular Weight: 370.583
• Hs Code.: 2934302300
• European Community (EC) Number: 200-044-2
• UNII: N3D6TG58NI
• DSSTox Substance ID: DTXSID6023656
• Nikkaji Number: J4.104A
• Wikipedia: Thioridazine
• Wikidata: Q58375
• NCI Thesaurus Code: C61971
• RXCUI: 10502
• Pharos Ligand ID: NWN99PURSF1L
• Metabolomics Workbench ID: 42994
• ChEMBL ID: CHEMBL479
• Mol file: 50-52-2.mol

Synonyms:Aldazine;Apo Thioridazine;Apo-Thioridazine;ApoThioridazine;Meleril;Mellaril;Melleretten;Melleril;Melleryl;Melzine;Rideril;Sonapax;Thioridazine;Thioridazine HCL;Thioridazine Hydrochloride;Thioridazine neurazpharm;Thioridazine-neurazpharm;Thioridazineneurazpharm;Thiozine

Chemical Property of Thioridazine

Chemical Property:

• Melting Point: 72-74°
• Refractive Index: 1.5800 (estimate)
• Boiling Point: 515.665 °C at 760 mmHg
• PKA: 9.5(at 25℃)
• Flash Point: 265.665 °C
• PSA: 57.08000
• Density: 1.237 g/cm³
• LogP: 5.88850
• Storage Temp.: ?20°C
• Solubility.: Practically insoluble in water, very soluble in methylene chloride, freely soluble in methanol, soluble in ethanol (96 per cent).
• Water Solubility.: 1.113mg/L(22.5 oC)
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 370.15374118
• Heavy Atom Count: 25
• Complexity: 432

Purity/Quality:

99.9% ^*data from raw suppliers

Thioridazine solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25-52/53
• Safety Statements: 16-36/37-45-61

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antipsychotic Agents
• Canonical SMILES: CN1CCCCC1CCN2C3=CC=CC=C3SC4=C2C=C(C=C4)SC
• Recent ClinicalTrials: Family Intervention in Recent Onset Schizophrenia Treatment (FIRST)
• Recent EU Clinical Trials: Cognitive effects of adjuntive Vortioxetine in early Schizophrenia
• Description: An antipsychotic drug of the phenothiazine class. It is of particular interest because of its “atypical” properties, some of which may be due to its extensive bioconversion to active metabolites. The therapeutic and side effects of thioridazine and its metabolites involve blockade of brain dopamine receptors, but also actions mediated via blockage of muscarininc cholinergic and α-adrenergic receptors.
• Uses: In terms of antipsychotic activity, thioridazine is inferior to aminazine. It is most effective in mental and emotional disorders accompanied by fear, stress, and excitement. It is prescribed for various forms of schizophrenia, psychosis, and neurosis. Mellaril(Novartis).
• Therapeutic Function: Tranquilizer

Technology Process of Thioridazine

There total 26 articles about Thioridazine 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: 26.0%

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-{2-[2-(methylthio)-10H-phenothiazin-10-yl]ethyl}piperidine-1-carboxylate → thioridazine (50-52-2,52496-67-0,57129-06-3,114488-10-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 50 ℃; for 18h; Inert atmosphere;

Reference yield:

N-(2-(1-methyl-2-piperidynyl)ethyl)-2-(2-fluorophenylthio)-5-(methylthio)aniline (129846-85-1) → thioridazine (50-52-2,52496-67-0,57129-06-3,114488-10-7)

Guidance literature:

With sodium hydride; In dimethyl sulfoxide; for 6.5h; Heating;

Reference yield:

1-chloro-4-(methylthio)-2-nitrobenzene (1199-36-6) → thioridazine (50-52-2,52496-67-0,57129-06-3,114488-10-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / K₂CO₃ / dimethylformamide / 3.5 h / 60 °C

2: 99 percent / active carbon, N₂H₄, FeCl₃*6H₂O / ethanol / 10 h / Heating

3: 23 percent / 80percent NaH / xylene / 3 h / Heating

4: 80percent NaH / dimethylsulfoxide / 6.5 h / Heating

With iron(III) chloride; sodium hydride; potassium carbonate; pyrographite; hydrazine hydrate; In ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; xylene;

upstream raw materials:

N-(2-(1-methyl-2-piperidynyl)ethyl)-2-(2-fluorophenylthio)-5-(methylthio)aniline

1-chloro-4-(methylthio)-2-nitrobenzene

2-fluorothiophenol

2-(2-fluorophenylthio)-5-(methylthio)aniline

Downstream raw materials:

mesoridazine

Thioridazine 5-sulfoxide

thioridazine Hydrochloride

Northioridazine

Refernces

• 1、 -. "THE (S)-ENANTIOMER OF MEPAZINE". Page/Page column 47; 49. . Retrieved 2015/01/16.
• 2、 Sindelar, Karel,Holubek, Jiri,Koruna, Ivan,Hrubantova, Marta. "MODIFIED SYNTHESES OF 2-(METHYLTHIO)-10-(2-(1-METHYL-2-PIPERIDINYL)ETHYL)PHENOTHIAZINE (THIORIDAZINE) AND 1-(3-(2-(METHYLSULFONYL)-10-PHENOTHIAZINYL)PROPYL)-PIPERIDINE-4-CARBOXAMIDE (METOPIMAZINE)". . p. 1586 - 1601. Retrieved 2007/10/02.