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FENFLURAMINE

FENFLURAMINE
FENFLURAMINE structure
CAS No.
458-24-2
Chemical Name:
FENFLURAMINE
Synonyms
S-768;Acino;Pesos;C06996;EQUINE;Obedrex;Rotondin;Pondimin;Ponderex;Adipomin
CBNumber:
CB1325500
Molecular Formula:
C12H16F3N
Formula Weight:
231.26
MOL File:
458-24-2.mol

FENFLURAMINE Properties

Melting point:
170°C
Boiling point:
bp12 108-112°
Density 
1.0950 (estimate)
storage temp. 
?20°C
pka
pKa 9.10 (Uncertain)
EWG's Food Scores
1
FDA UNII
2DS058H2CF
SAFETY
  • Risk and Safety Statements
Hazard Codes  F,T
Risk Statements  11-23/24/25-39/23/24/25
Safety Statements  16-36/37-45
Toxicity LD50 i.p. in mice: 144 mg/kg

FENFLURAMINE Chemical Properties,Uses,Production

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 It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertensio .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

FENFLURAMINE Preparation Products And Raw materials

Raw materials

Preparation Products

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