404-82-0

Basic information

• Product Name: Fenfluramine hydrochloride
• Synonyms: FENFLURAMINE HYDROCHLORIDE MM(CRM STANDARD);N-Ethyl-α-methyl-3-[trifluoromethyl] benzeneethanamine hydrochloride;N-Ethyl-a-methyl-3-(trifluoromethyl)benzeneethanamine Hydrochloride;(+)-n-ethyl-α-methyl-m-[trifluoromethyl]phenethylamine hydrochloride;rac Fenfluramine Hydrochloride;BenzeneethanaMine,N-ethyl-a-Methyl-3-(trifluoroMethyl)-,hydrochloride (1:1);(+)-N-Ethyl-α-methyl-m-[trifluoromethyl]phenethylamine;n-ethyl-1-[3-(trifluoromethyl)phenyl]-propan-2-amine
• CAS NO: 404-82-0
• Molecular Formula: C₁₂H₁₆F₃N*ClH
• Molecular Weight: 267.72
• EINECS: 206-968-2
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Amines;Aromatics
• Mol File: 404-82-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 1660C
• Boiling Point: 243.1 °C at 760 mmHg
• Flash Point: 100.8 °C
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Fenfluramine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Fenfluramine hydrochloride(404-82-0)
• EPA Substance Registry System: Fenfluramine hydrochloride(404-82-0)

Safety Data

• Hazard Codes: T
• Statements: 25-23/24/25
• Safety Statements: 7-16-36/37-45-36/37/39-22
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: DA0295500
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 404-82-0(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline Solid

Definition

ChEBI: The hydrochloride salt of fenfluramine. It binds to the serotonin reuptake 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 behavior located in the hypothalamus. This suppresses the appetite for carbohydrates. Fenfluramine hydrochloride was used for treatment of diabetes and obesity. It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertension.

Brand name

Pondimin (Robins).

General Description

Fenfluramine hydrochloride, (±)N-ethyl- -methyl-m-(trifluoromethyl)phenethylamine hydrochloride (Pondimin), isunique in this group of drugs, in that it tends to produce sedationrather than excitation. Effects are said to be mediatedprincipally by central serotoninergic, rather than central noradrenergic,mechanisms. In large doses in experimental animals,the drug is a serotonin neurotoxin.It was withdrawnfrom human use after reports of heart valve damage and pulmonaryhypertension. From its structure, more apolar or hydrophobiccharacter than amphetamine, tropism for serotoninergicneurons would be expected. Likewise, thestructure suggests an indirect mechanism. If an indirectmechanism were operative, then all postsynaptic 5-HT receptors could be activated. Evidence from several studies indicatesthat the 5-HT1B and the 5-HT2C receptors are mostresponsible for the satiety effects of 5-HT. 5-HT may alsoinfluence the type of food selected (e.g., lower-fat food intake).The(+) isomer, dexfenfluramine (Redux), has agreater tropism for 5-HT systems than the racemic mixture.It, too, was withdrawn because of toxicity.

Safety Profile

Poison by ingestion, intravenous, and intraperitoneal routes. Human systemic effects by ingestion: mydriasis, change in motor activity, nausea. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits very toxic fumes of F-, NOx, and HCl

InChI:InChI=1/C12H16F3N.ClH/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15;/h4-6,8-9,16H,3,7H2,1-2H3;1H/p-1

Upstream product

• 21906-39-8 3-(trifluoromethyl)phenylacetone 
• 557-66-4 ethanamine hydrochloride 
• 98-16-8 3-trifluoromethylaniline 
• 2338-76-3 3-trifluoromethylphenylacetonitrile 
• 351-35-9 3-(trifluoromethyl)phenylacetic acid 
• 458-24-2 Fenfluramine 

Relevant articles and documents

POLYMORPH OF N-ETHYL-1-(3-(TRIFLUOROMETHYL)PHENYL)PROPAN-2-AMINE HYDROCHLORIDE AND PROCESS FOR PREPARATION THEREOF

The present invention relates to a crystalline form of N-ethyl-1-(3-(trifluoro methyl) phenyl) propan-2-amine hydrochloride compound of formula-1, which is represented by the following structural formula. The present invention also relates to process for the preparation of crystalline form of compound of formula-1 and process for the preparation of compound of formula-1.

FENFLURAMINE COMPOSITIONS AND METHODS OF PREPARING THE SAME

Methods of preparing a fenfluramine active pharmaceutical ingredient are provided. Aspects of the method include (a) hydrolyzing a 2-(3-(trifluoromethyl)phenyl)acetonitrile composition to produce a 2-(3-(trifluoromethyl)phenyl)acetic acid composition; (b) reacting the 2-(3-(trifluoromethyl)phenyl)acetic acid composition with acetic anhydride and a catalyst to produce a 1-(3-(trifluoromethyl)phenyl)propan-2-one composition; and (c) reductively aminating the 1-(3-(trifluoromethyl)phenyl)propan-2-one composition with ethylamine using a borohydride reducing agent to produce a fenfluramine composition. Also provided are compositions and pharmaceutical ingredients prepared according to the subject methods including a pharmaceutically acceptable salt of fenfluramine and having less than 0.2% by weight in total of trifluoromethyl regioisomers.