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Fluoxetine hydrochloride

Basic information Antidepressants Safety Related Supplier
Fluoxetine hydrochloride Basic information
Fluoxetine hydrochloride Chemical Properties
  • Melting point:158-159°C
  • alpha -0.05~+0.05°
  • Flash point:9℃
  • storage temp. 2-8°C
  • solubility H2O: soluble (sparingly)
  • form solid
  • color white
  • Water Solubility Soluble in dimethylsulfoxide and water.
  • InChIKeyGIYXAJPCNFJEHY-UHFFFAOYSA-N
  • CAS DataBase Reference56296-78-7(CAS DataBase Reference)
  • EPA Substance Registry SystemFluoxetine hydrochloride (56296-78-7)
Safety Information
Fluoxetine hydrochloride Usage And Synthesis
  • AntidepressantsFluoxetine hydrochloride is a selective serotonin reuptake inhibitor (SSRI),it is adapted to the treatment of various depressive disorders, including mild or major depression, bipolar disorder depression, psychogenic depression and depressive neurosis. The mechanism is inhibiting neuronal uptake of serotonin from the synaptic cleft, increasing this neurotransmitter in the gap for practical use , thereby improving the emotional state,and treating depressive disorders. Common adverse reactions are dry mouth, loss of appetite, nausea, insomnia, fatigue,  a few cases of anxiety and headaches are seen . Because fluoxetine hydrochloride has longer half-life, patients whose liver and kidney function are poor or elderly patients, should appropriately reduce the dose. Children should be applied in accordance with the doctor's advice. Patients who has the history of epilepsy, pregnancy or lactation women should use with caution . If rash or fever occurs, the drug should be discontinued immediately and symptomatic treatment should be given. It  is not appropriate to be used with monoamine oxidase inhibitor (MAOI) ; if necessary, the drug should be discontinued after five weeks, before switching to a monoamine oxidase inhibitor (MAOI).
  • DescriptionFluoxetine hydrochloride is a serotonin-selective antidepressant approved for the treatment of major depressive disorders, including those with concomitant anxiety. It also appears effective in the treatment of obesity.
  • Chemical PropertiesWhite to Off-White Powder
  • OriginatorLilly (USA)
  • UsesA labelled selective serotonin reuptake inhibitor (SSRI). Used as an antidepressant.
  • UsesA selective serotonin reuptake inhibitor (SSRI). Used as an antidepressant.
  • UsesA selectiive derotonin reuptake inhibitor. Used as an antidepressant
  • Manufacturing ProcessAbout 600 g of β-dimethylaminopropiophenone hydrochloride were converted to the corresponding free base by the action of 1.5 N aqueous sodium hydroxide. Free base was dissolved in 2 L of THF, and the resulting solution added in dropwise fashion to a solution of 4 moles of diborane in 4 L of THF. The reaction mixture was stirred overnight. An additional mole of diborane in 1 L of THF was added, and the reaction mixture stirred again overnight. Next, 2 L of aqueous hydrochloric acid were added to decompose any excess diborane present. The tetrahydrofuran was removed by evaporation. The acidic solution was extracted twice with 1 L portions of benzene, and the benzene extracts were discarded. The acidic solution was then made basic with an excess of 5 N aqueous sodium hydroxide. The basic solution was extracted three times with 2 L portions of benzene. The combined extracts washed with a saturated aqueous sodium chloride and then dried. Evaporation of the solvent in vacuo yields 442 g of N,N-dimethyl-3-phenyl-3hydroxypropylamine.
    A solution containing 442 g of N,N-dimethyl-3-phenyl-3-hydroxypropylamine in 5 L of chloroform was saturated with dry gaseous hydrogen chloride. 400 mL of thionyl chloride were then added to the solution at a rate sufficient to maintain reflux. The solution was refluxed an additional 5 hours. Evaporation of the chloroform and other volatile constituents in vacuo yielded N,Ndimethyl-3-phenyl-3-chloropropylamine hydrochloride which was collected by filtration, and the filter cake washed twice with 1.5 L portions of acetone. The washed crystals weighed about 500 g and melted at 181-183°C with decomposition. An additional 30 g of compound were obtained from the acetone wash by standard crystallization procedures. The structure of the above compound was verified by NMR and titration.
    A solution of 50 g p-trifluoromethylphenol, 12 g of solid sodium hydroxide and 400 mL of methanol were added 29.8 g of N,N-dimethyl 3-phenyl-3chloropropylamine hydrochloride. The resulting reaction mixture was refluxed for about 5 days and then cooled. The methanol was removed by evaporation, and the resulting residue taken up in a mixture of ether and 5 N aqueous sodium hydroxide. The ether layer was separated and washed twice with 5 N aqueous sodium hydroxide and three times with water. The ether layer was dried, and the ether removed by evaporation in vacuo to yield as a residue N,N-dimethyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine.
    To a solution 8.1 g of cyanogen bromide in 500 mL benzene and 50 mL of toluene at 5°C in nitrogen was added dropwise a solution of 12.146 g of N,Ndimethyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine in 40 mL of benzene. The temperature of the reaction mixture was allowed to rise slowly to room temperature, at which temperature stirring was continued overnight while still maintaining a nitrogen atmosphere. 100 mL of benzene were added. The reaction mixture was washed twice with water, once with 2 N aqueous sulfuric acid and then with water until neutral. The organic layer was dried, and the solvents removed therefrom by evaporation in vacuo to yield about 9.5 g of an oil comprising N-methyl-N-cyano-3-(p-trifluoromethylphenoxy)-3phenylpropylamine.
    The reaction mixture containing 100 g potassium hydroxide, 85 mL water, 400 mL ethylene glycol and 9.50 g of N-methyl-N-cyano-3-(ptrifluoromethylphenoxy)-3-phenylpropylamine was heated to refluxing temperature for 20 hours, and was then cooled. 500 mL of water were added. The reaction mixture was extracted with three 500 mL portions of ether. The combined extracts washed with water. The water wash was discarded. The ether solution was next contacted with 2 N aqueous hydrochloric acid. The acidic aqueous layer was separated. A second aqueous acidic extract with 2 N hydrochloric acid was made followed by three aqueous extracts and an extract with saturated aqueous sodium chloride. The aqueous layers were all combined and made basic with 5 N aqueous sodium hydroxide. N-methyl 3(p-trifluoromethylphenoxy)-3-phenylpropylamine, formed in the above reaction, was insoluble in the basic solution and separated. The amine was extracted into ether. Two further ether extractions were carried out. The ether extracts were combined, and the combined extracts washed with saturated aqueous sodium chloride and then dried. Evaporation of the ether in vacuo yielded about 6.3 g of N-methyl-3-(p-trifluoromethylphenoxy)-3phenylpropylamine. The amine free base was converted to the corresponding hydrochloride salt.
  • brand nameProzac (Lilly); Sarafem (Lilly); Sarafem (Warner Chilcott).
  • Therapeutic FunctionAntidepressant
  • Biological ActivitySelective serotonin reuptake inhibitor. Binds to the human 5-HT transporter with a K i of 0.9 nmol/l and is between 150- and 900- fold selective over 5-HT 1A , 5-HT 2A , H 1 , α 1 , α 2 -adrenergic, and muscarinic receptors. Antidepressant. Also available as part of the Serotonin Uptake Inhibitor Tocriset™ .
Fluoxetine hydrochloride Preparation Products And Raw materials
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