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(+)-FENFLURAMINE HYDROCHLORIDE

(+)-FENFLURAMINE HYDROCHLORIDE Basic information
Product Name:(+)-FENFLURAMINE HYDROCHLORIDE
Synonyms:FENFLURAMINEHCL(DEXTRO-);(S)-N-Ethyl-α-methyl-3-(trifluoromethyl)benzeneethanamine;[S,(+)]-N-Ethyl-α-methyl-m-(trifluoromethyl)phenethylamine;ethyl-[1-methyl-2-[3-(trifluoromethyl)phenyl]ethyl]amine;(+)-FENFLURAMINE HYDROCHLORIDE--DEA*SCHE DULE IV ITE;DBGIVFWFUFKIQN-VIFPVBQESA-N;d-n-ethyl-alpha-methyl-m-trifluoromethylphenethylamine;redux
CAS:3239-44-9
MF:C12H16F3N
MW:231.26
EINECS:
Product Categories:
Mol File:3239-44-9.mol
(+)-FENFLURAMINE HYDROCHLORIDE Structure
(+)-FENFLURAMINE HYDROCHLORIDE Chemical Properties
alpha D25 +9.5° (c = 8 in ethanol)
Boiling point 108-112 °C(Press: 12 Torr)
density 1.078±0.06 g/cm3(Predicted)
pka10.23±0.19(Predicted)
Safety Information
Hazard Codes T
Risk Statements 23/24/25
Safety Statements 22-36/37/39-45
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS SH6824000
Hazardous Substances Data3239-44-9(Hazardous Substances Data)
ToxicityLD50 orally in rats: 114.6 mg/kg (Le Douarec)
MSDS Information
ProviderLanguage
SigmaAldrich English
(+)-FENFLURAMINE HYDROCHLORIDE Usage And Synthesis
OriginatorDexfenfluramine,Interneuron Pharmaceuticals (Lexington, Mass), for Wyeth Laboratories Inc
UsesAppetite suppressant (systemic).
DefinitionChEBI: The S-enantiomer of fenfluramine. It stimulates the release of serotonin and selectively inhibits its reuptake, but unlike fenfluramine it does not possess catecholamine agonist activity. It was formerly given by mouth as the hydrochloride in the treatment of obesity, but, like fenfluramine, was withdrawn wolrdwide following reports of valvular heart defects.
Manufacturing ProcessTo 10.65 parts acetic anhydride there were added, with cooling, 8 parts 1-(3- trifluoromethylphenyl)-2-aminopropane and 100 parts water. The mixture was neutralized with 30 parts sodium carbonate. The organic layer was extracted twice with 50 parts ether. The ether solutions were washed with 25 parts water and dried over potassium carbonate. On distillation there were obtained 9 parts 1-(3-trifluoromethylphenyl)-2-acetyl-aminopropane. 9 parts of it were reduced in solution in 100 parts ether with 1.7 parts lithium and aluminium hydride with 20 parts ether. The suspension was refluxed for 4 hours, hydrolysed with 2 parts water, 2 parts 4 N sodium hydroxide and then 6 parts water. The precipitate was drained washed with 50 parts ether, the filtrate was extracted twice with 50 parts 0.5 N sulfuric acid. The acidic layers were separated by sedimentation and neutralized with 100 parts 4 N sodium hydroxide, the separated amine was extracted with 200 parts ether. There were obtained 6 parts 1-(3-trifluoromethylphenyl)-2-ethylaminopropane (boiling point 108°-112°C at 12 mm). The hydrochloride thereof was recrystallized from mixture of ethyl alcohol and ether (melting point 166°C).
S-Isomer was prepared the next way. To a solution of 160 parts of dibenzoyl d-tartaric acid in 1600 parts of anhydrous ethanol were added for 15 minutes 80 parts of dl-1-(3-trifluoromethylphenyl)-2-ethylaminopropane. After 15 additional minutes, 90.5 parts of crystalline solid were isolated. When this product was recrystallized from 1300 parts of anhydrous ethanol, there was obtained 70 parts of dibenzoyl d-tartarate acid salt of L-1-(3- trifluoromethylphenyl)-2-ethylaminopropane. This salt was treated with 500 parts of 4 N NaOH. The mixture was extracted with 2x200-part portions of diethyl ether and the ether extract was re-extracted with 100 parts of 4 N hydrodiboric acid. After treatment with 120 parts of 4 N NaOH, the free amine amounting to 25 parts distills at 105°-107°C (17.5 mm.). [α]D25: - 9.6° (c=8% in ethanol).
Brand nameRedux (Interneuron);Diomeride.
Therapeutic FunctionAntiobesity
(+)-FENFLURAMINE HYDROCHLORIDE Preparation Products And Raw materials
Raw materialsDIBENZOATE-->Lithium Aluminum Hydride-->Norfenfluramine-->D-Tartaric acid
Tag:(+)-FENFLURAMINE HYDROCHLORIDE(3239-44-9) Related Product Information
(+)-Fenfluramine hydrochloride,S(+)-FENFLURAMINE HYDROCHLORIDE SEROTONI N UPTAKE INHI (+/-)-FENFLURAMINE HYDROCHLORIDE,FENFLURAMINE HYDROCHLORIDE,FENFLURAMINE HYDROCHLORIDE MM(CRM STANDARD) FENFLURAMINE HYDROCHLORIDE,fenfluramine hydrochloride*methanol solution,FENFLURAMINE HYDROCHLORIDE--DEA*SCHEDULE IV ITEM,(+/-)-FENFLURAMINE HYDROCHLORIDE R(-)-FENFLURAMINE HYDROCHLORIDE (R)-ALPHA-(3-TRIFLUOROMETHYL-BENZYL)-PROLINE-HCL (S)-2-{Bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl}pyrrolidine (+)-FENFLURAMINE HYDROCHLORIDE (R)-3-(3-TRIFLUOROMETHYL-BENZYL)-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER (R)-2-(3-TRIFLUOROMETHYL-BENZYL)-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER (S)-ALPHA-(3-TRIFLUOROMETHYL-BENZYL)-PROLINE-HCL (R)-2-(3,5-BIS-TRIFLUOROMETHYL-BENZYL)-PIPERAZINE (S)-2-{Bis[3,5-bis(trifluoromethyl)phenyl]methoxy-methyl}pyrrolidine hydrochloride BOC-(S)-ALPHA-(3-TRIFLUOROMETHYL-BENZYL)-PROLINE (R)-3-(3-TRIFLUOROMETHYL-BENZYL)-PIPERAZIN-2-ONE (R)-2-(3,5-BIS-TRIFLUOROMETHYL-BENZYL)-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER BOC-(R)-ALPHA-(3-TRIFLUOROMETHYL-BENZYL)-PROLINE (R)-3-(3,5-BIS-TRIFLUOROMETHYL-BENZYL)-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilanyloxy)methyl]pyrrolidine, (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilyloxy)methyl]pyrrolidine, (S)-α,α-[3,5-Bis(trifluoromethyl)phenyl]prolinol trimethylsilyl ether