FENFLURAMINE
- CAS No.
- 458-24-2
- Chemical Name:
- FENFLURAMINE
- Synonyms
- EQUINE;Acino;Pesos;S-768;C06996;Obedrex;Adipomin;Ponderex;Pondimin;Rotondin
- CBNumber:
- CB1325500
- Molecular Formula:
- C12H16F3N
- Molecular Weight:
- 231.26
- MDL Number:
- MFCD00864474
- MOL File:
- 458-24-2.mol
| 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 |
| EWG's Food Scores | 1 |
| FDA UNII | 2DS058H2CF |
| ATC code | A08AA02,N03AX26 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS06 |
|---|---|
| Signal word | Danger |
| Hazard statements | H301 |
| Precautionary statements | P264-P270-P301+P310-P321-P330-P405-P501 |
| 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
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 It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertensio .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 Preparation Products And Raw materials
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