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FENFLURAMINE

FENFLURAMINE Basic information
Product Name:FENFLURAMINE
Synonyms:FENFLURAMINE;AURORA KA-7683;AURORA KA-7684;1-(meta-Trifluoromethyl-phenyl)-2 ethylaminopropane;3-(Trifluoromethyl)-N-ethyl-alpha-methylphenethylamine;Acino;Adipomin;N-Ethyl-1-[3-(trifluoromethyl)phenyl]-2-propanamine
CAS:458-24-2
MF:C12H16F3N
MW:231.26
EINECS:207-276-3
Product Categories:
Mol File:458-24-2.mol
FENFLURAMINE Structure
FENFLURAMINE Chemical Properties
Melting point 170°C
Boiling point bp12 108-112°
density 1.0950 (estimate)
storage temp. -20°C
solubility Chloroform (Slightly), Methanol (Slightly)
pkapKa 9.10 (Uncertain)
form Oil
color Colourless to Pale Yellow
Stability:Hygroscopic
CAS DataBase Reference458-24-2
Safety Information
Hazard Codes F,T
Risk Statements 11-23/24/25-39/23/24/25
Safety Statements 16-36/37-45
Hazardous Substances Data458-24-2(Hazardous Substances Data)
ToxicityLD50 i.p. in mice: 144 mg/kg
MSDS Information
FENFLURAMINE Usage And Synthesis
OriginatorObenon,Neofarma
UsesAnorexic.
DefinitionChEBI: A secondary amino compound that is 1-phenyl-propan-2-amine in which one of the meta-hydrogens is substituted by trifluoromethyl, and one of the hydrogens attached to the nitrogen is substituted by an ethyl group. It binds to the serotonin reu take pump, causing inhbition of serotonin uptake and release of serotonin. The resulting increased levels of serotonin lead to greater serotonin receptor activation which in turn lead to enhancement of serotoninergic transmission in the centres of feeding ehavior located in the hypothalamus. This suppresses the appetite for carbohydrates. Fenfluramine was used as the hydrochloride for treatment of diabetes and obesity. It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertensio .
Manufacturing Process38.5 parts of (trifluoromethyl-3'-phenyl)-1-oximino-2-propane in 550 parts of ethanol (with ammonia) was hydrogenated under pressure of hydrogen 90 kg with a catalyst nickel Reney (20 parts). After a completion of reaction to the reaction mixture was added 1000 parts of water and 300 parts of hydrochloric acid. The mixture was concentrated in vacuo and extracted with 450 parts of ether. To an aqueous phase was added the sodium carbonate and the mixture was extracted with 500 parts of ether. Organic phase was concentrated in vacuo to obtain 29 g of 1-(meta-trifluoromethyl-phenyl)-2-ethylaminopropane. B.P. 96°C at 17 mm.
Brand namePondimin (Robins).
Therapeutic FunctionAnorexic
World Health Organization (WHO)Fenfluramine, dexfenfluramine and phentermine were approved individually more than 20 years ago in the USA for single-drug, short-term treatment of obesity. The manufacturers of fenfluramine and dexfenfluramine have since voluntarily withdrawn both products from the market worldwide. Phentermine remains available.
Flucetorex 1-(alpha-Methyl-m-trifluoromethylphenethylamino)acetylurea BENFLUOREX HYDROCHLORIDE (R)-ALPHA-(3-TRIFLUOROMETHYL-BENZYL)-PROLINE-HCL FENFLURAMINE-D10 FENFLURAMINE N,N-Diethyl-alpha-methyl-m-trifluoromethylphenethylamine R(-)-FENFLURAMINE HYDROCHLORIDE alpha-Methyl-N-(3-phenyl-2-propynyl)-m-trifluoromethylphenethylamine BOC-(S)-ALPHA-(3-TRIFLUOROMETHYL-BENZYL)-PROLINE N-(2-Chloroethyl)-alpha-methyl-m-trifluoromethylphenethylamine BOC-(R)-ALPHA-(3-TRIFLUOROMETHYL-BENZYL)-PROLINE 2-(3-TRIFLUOROMETHYL-BENZYL)-PIPERAZINE FENFLURAMINE HYDROCHLORIDE (+)-FENFLURAMINE HYDROCHLORIDE,(+)-fenfluramine hydrochloride--dea*schedule iv I,(s)-fenfluramin N-NITROSOFENFLURAMINE (S)-ALPHA-(3-TRIFLUOROMETHYL-BENZYL)-PROLINE-HCL R(-)-FENFLURAMINE HYDROCHLORIDE LESS ACT IVE ENANTIOME,l-fenfluramin
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