Fupentixol dihydrochloride

Fupentixol dihydrochloride Basic information
Product Name:Fupentixol dihydrochloride
Synonyms:4-(3-(2-(trifluoromethyl)thioxanthen-9-ylidene)propyl)-1-piperazineethanold;4-(3-(2-trifluoromethylthioxanth-9-ylidene)propyl)-1-piperazineethanodih;flupentixolhydrochloride;fx703;thioxanthene,9-(3-(4-(2-hydroxyethyl)piperazinyl)propylidene)-2-trifluoromethy;2-[4-[3-[(EZ)-2-(TRIFLUOROMETHYL)-9H-THIOXANTHEN-9-YLIDENE]PROPYL] PIPERAZIN-1-YL]ETHANOL DIHYDROCHLORIDE;(4-[3-[2-TRIFLUOROMETHYL)-9H-THIOXANTHEN-9-YLIDENE]PROPYL]-1-PIPERAZINEETHANOL 2HCL;FUPENTIXOL DIHYDROCHLORIDE
CAS:2413-38-9
MF:C23H25F3N2OS.2ClH
MW:507.44
EINECS:219-321-4
Product Categories:Antipsychotic;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
Mol File:2413-38-9.mol
Fupentixol dihydrochloride Structure
Fupentixol dihydrochloride Chemical Properties
Melting point 237-239 °C(Solv: ethanol (64-17-5); methanol (67-56-1))
storage temp. Sealed in dry,2-8°C
solubility H2O: soluble
form solid
color white or off-white
Water Solubility soluble
CAS DataBase Reference2413-38-9
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22
Safety Statements 36/37/39
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS TL9900000
ToxicityLD50 oral in rat: 791mg/kg
MSDS Information
ProviderLanguage
SigmaAldrich English
Fupentixol dihydrochloride Usage And Synthesis
Chemical PropertiesLight Brown Solid
OriginatorEmergil ,Labaz, France,1971
UsesNeuroleptic agent related structurally to thiothixene. Antipsychotic; neuroleptic agent; dopamine receptor antagonist.
DefinitionChEBI: Cis-flupenthixol dihydrochloride is the dihydrochloride salt of cis-flupenthixol. It has a role as a geroprotector. It contains a cis-flupenthixol(2+).
Manufacturing ProcessA mixture of 200 grams of 2-benzoyloxyethanol in 2 liters of pyridine at -5°C is treated with 275 grams of p-toluenesulfonyl chloride and the resulting mixture is stirred at 0°C for 2 hours. Water is added slowly at 0° to 5°C. Extracting with chloroform, washing the extract with dilute hydrochloric acid, water and potassium bicarbonate, and evaporating the solvent leaves benzyloxyethyl p-toluenesulfonate.
A mixture of 186 grams of the above prepared p-toluenesulfonate, 106 grams of N-ethoxycarbonylpiperazine, 44 grams of potassium carbonate and 800 ml of toluene is refluxed for 21 hours, then filtered and extracted with dilute hydrochloric acid. The extract is basified with sodium hydroxide and extracted into chloroform. Evaporation of the chloroform and distillation of the residue in vacuo gives 1-benzyloxyethyl-4-ethoxy-carbonylpiperazine, BP 153° to 156°C (0.15 mm).
Hydrolysis and decarboxylation of this ester (188 grams) is accomplished by refluxing with 155 grams of potassium hydroxide, 155 ml of water and 1,550 ml of ethanol for four days. Filtering, concentrating, adding water to the residue, acidifying with hydrochloric acid, heating to 90°C, saturating with potassium carbonate, extracting into chloroform, evaporating and distilling the chloroform gives N-benzoyloxyethylpiperazine.
A mixture of 50 grams of the above prepared piperazine, 30.1 grams of sodium carbonate and 200 ml of benzene is heated to reflux and treated with 39.5 grams of 3-bromopropanol over 1.5 hours. The resulting mixture is refluxed for 2 hours, then filtered, extracted with dilute hydrochloric acid, basified, extracted with benzene, and the extracts are concentrated and distilled to give l-benzyloxyethyl-4-(3-hydroxypropyl)-piperazine, BP 188° to 190°C (0.15 mm). The free base is converted to the dihydrochloride salt by treatment of an alcoholic solution with ethereal hydrogen chloride to separate the salt.
Thionyl chloride (67 grams) is added over 15 minutes to a mixture of 39.5 grams of the above prepared dihydrochloride salt and 400 ml of chloroform. Refluxing for 4 hours, cooling and filtering yields the dihydrochloride salt of lbenzyloxyethyl-4-(3-chloropropyl)-piperazine, MP 201° to 202°C. The salt in aqueous solution is basified. Extraction with ether and evaporation of the solvent yields the free base.
Magnesium (1.3 grams) in 8 ml of refluxing tetrahydrofuran is treated with 1 ml of ethyl bromide. A solution of 22.7 grams of l-benzyloxyethyl-4-(3chloropropyl)-piperazine in 50 ml of tetrahydrofuran is added slowly and the mixture is refluxed for 1 hour.
A solution of 13.2 grams of 2-trifluoromethyl-9-xanthenone in tetrahydrofuran is added over 1 hour to 16.0 grams of 3-(4-benzyloxyethyl-1-piperazinyl) propylmagnesium chloride, prepared as above, in tetrahydrofuran while gentlyrefluxing. Refluxing is continued for 2 hours. Concentrating, pouring the residue into ammonium chloride, ice and water, extracting with ether, evaporating the extracts and treating the residue with concentrated hydrochloric acid at 95°C for 1 hour gives a mixture of cis and trans 9-[3-(4hydroxyethyl-1-piperazinyl)propylidene]-2-trifluoromethylxanthene dihydrochloride. Fractional crystallization from ethanol-ether separates the isomers. The free bases are obtained by neutralizing an aqueous solution of the dihydrochloride, extracting into ether and evaporating the ether in vacuo.





Therapeutic FunctionTranquilizer
Biological Activitymic: 10-100 μg/ml in most of the strainsflupenthixol, introduced in 1965 by lundbeck, marketed under brand names such asdepixol.flupenthixolis atypical antipsychoticdrugof thethioxantheneclass. in addition to single drug preparations, flupenthixol is also available asflupentixol/melitracen, which is acombination product.
in vitrothe minimum inhibitory concentration of flupenthixol was determined by the national committee for clinical laboratory standards agar dilution method. mics ranged from 10–100 μg/ml for most of the strains, whilst some strains were inhibited at even lower concentrations. the mode of action of flupenthixol was found to be bacteriostatic against staphylococcus aureus and vibrio cholerae [1].
in vivoin the in vivo experiments, flupenthixol was able to contribute significant protection to a swiss strain of white mice challenged with 50 median lethal dose of a mouse-virulent strain at a drug concentration of 15 μg/mouse. moreover, flupenthixol reduced remarkably the number of viable bacteria in organs and blood of mice treated with flupenthixol [1].
storageDesiccate at RT
references[1] jeyaseeli l,gupta ad,asok kumar k,mazumdar k,dutta nk,dastidar sg. antimicrobial potentiality of the thioxanthene flupenthixol through extensive in vitro and in vivo experiments. int j antimicrob agents.2006 jan;27(1):58-62.
[2] kong ds,yeo sh. an open
Fupentixol dihydrochloride Preparation Products And Raw materials
Raw materialsMagnesium-->Hydrochloric acid-->Ethyl N-piperazinecarboxylate-->2-Benzyloxyethanol-->Thionyl chloride-->3-Bromo-1-propanol-->Bromoethane-->Tosyl chloride-->Potassium hydroxide
Piperacillin EQUILIN Fupentixol dihydrochloride Propyl gallate N-Aminoethylpiperazine Sibutramine hydrochloride Tramadol hydrochloride 1-Methylpiperazine ETHANOLAMINE HYDROCHLORIDE Thioxanthen-9-one 2-Ethylhexyl ferulate Piperazine Cetirizine hydrochloride 1-AdaMantanethylaMine Homopiperazine Dihydrochloride Diphenhydramine Hydrochloride Propyl butyrate

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