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)

pka

pKa 9.10 (Uncertain)

form 

Oil

color 

Colourless to Pale Yellow

Stability:

Hygroscopic

CAS DataBase Reference

458-24-2

Safety Information

Hazard Codes 

F,T

Risk Statements 

11-23/24/25-39/23/24/25

Safety Statements 

16-36/37-45

Hazardous Substances Data

458-24-2(Hazardous Substances Data)

Toxicity

LD50 i.p. in mice: 144 mg/kg

FENFLURAMINE Usage And Synthesis

Description

Fenfluramine is the only marketed anorectic agent that exerts its appetite depressant effect via a serotoninrgic mechanism. Its major metabolite, norfenfluramine, is believed to be the main active form in humans .

Originator

Obenon,Neofarma

Uses

Anorexic.

Definition

ChEBI: 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 It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertensio .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 Process

38.5 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 name

Pondimin (Robins).

Therapeutic Function

Anorexic

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.

Synthesis

Fenfluramine is prepared by reductive alkylation of norfenfluramine with acetaldehyde . The nor compound is obtained by catalytic hydrogenation of the oxime made from 3-trifluoromethlyphenyl acetone (Eq. 2).

FENFLURAMINE(458-24-2)Related Product Information

• R(-)-FENFLURAMINE HYDROCHLORIDE LESS ACT IVE ENANTIOME,l-fenfluramin
• (+)-FENFLURAMINE HYDROCHLORIDE,(+)-fenfluramine hydrochloride--dea*schedule iv I,(s)-fenfluramin
• BENFLUOREX HYDROCHLORIDE
• FENFLURAMINE
• Flucetorex
• FENFLURAMINE HYDROCHLORIDE
• S(+)-FENFLURAMINE HYDROCHLORIDE SEROTONI N UPTAKE INHI,(+)-Fenfluramine hydrochloride,(+)-Fenfluramine Hydrochlorid
• Fenfluramine hydrochloride
• DL-3-(4-Fluorophenyl)alanine
• 3-FLUORO-D-PHENYLALANINE
• 6-Fluorotryptamine hydrochloride
• 2-PhenylethylaMine
• 3-(TRIFLUOROMETHYL)PHENETHYLAMINE
• N-NITROSOFENFLURAMINE
• (R)-ALPHA-(3-TRIFLUOROMETHYL-BENZYL)-PROLINE-HCL
• R(-)-FENFLURAMINE HYDROCHLORIDE
• (S)-ALPHA-(3-TRIFLUOROMETHYL-BENZYL)-PROLINE-HCL
• N,N-Diethyl-alpha-methyl-m-trifluoromethylphenethylamine