3239-45-0

Basic information

• Product Name: (+)-Fenfluramine hydrochloride
• Synonyms: (S)-N-ethyl-alpha-methyl-m-(trifluoromethyl)phenethylamine hydrochloride;S(+)-FENFLURAMINE HYDROCHLORIDE SEROTONI N UPTAKE INHI;(+)-Fenfluramine Hydrochlorid;(+)-N-Ethyl-a-methyl-m-(trifluoromethyl)phenethylamine Hydrochloride;(aS)-N-Ethyl-a-methyl-3-(trifluoromethyl)benzeneethanamine Hydrochloride;Glypolix;Isomeride;S5614 HCl
• CAS NO: 3239-45-0
• Molecular Formula: C12H17ClF3N
• Molecular Weight: 267.7182896
• EINECS: 221-806-0
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Amines;Aromatics
• Mol File: 3239-45-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 159-163°C
• Boiling Point: 243.1 °C at 760 mmHg
• Flash Point: 100.8 °C
• Appearance: white to off-white/
• Storage Temp.: Desiccate at RT
• Solubility: H2O: soluble10mg/mL
• CAS DataBase Reference: (+)-Fenfluramine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Fenfluramine hydrochloride(3239-45-0)
• EPA Substance Registry System: (+)-Fenfluramine hydrochloride(3239-45-0)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 22-36/37/39-45
• RIDADR: UN 2811
• WGK Germany: 3
• RTECS: SH6824000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 3239-45-0(Hazardous Substances Data)

Usage

Description

(+)-Fenfluramine hydrochloride, also known as Redux, is a white crystalline powder that was formerly used as an anorexic agent for the treatment of obesity. It is the (+)-isomer of fenfluramine, obtained by resolution using d-camphoric acid and conversion to the HCl salt. (+)-Fenfluramine hydrochloride selectively stimulates the release of serotonin and inhibits its reuptake, without possessing catecholamine agonist activity. It acts as a 5-HT agonist, with no dopaminergic or noradrenergic activity, and is involved in various mechanisms such as inhibiting the presynaptic release of serotonin, being a reuptake inhibitor, a 5-HT1B receptor agonist, and a postsynaptic 5-HT2C receptor agonist.

Uses

Used in Pharmaceutical Industry:
(+)-Fenfluramine hydrochloride is used as an anorexic agent for the treatment of obesity. It was marketed under the brand name Redux in Europe, Canada, and the US. (+)-Fenfluramine hydrochloride works by increasing serotonin levels in the brain, which helps suppress appetite and promote weight loss. However, due to its side effects, including primary pulmonary hypertension, brain serotonin neurotoxicity, and valvular heart disease, Redux was withdrawn worldwide.
Used in Research and Development:
(+)-Fenfluramine hydrochloride is also used in research and development for studying the effects of serotonin on appetite and weight regulation. Its selective action on serotonin pathways provides valuable insights into the development of new drugs for obesity treatment, with a focus on minimizing side effects.

Originator

Servier (France)

Biological Activity

Indirectly agonizes serotonin receptors via inhibition of 5-HT re-uptake and stimulation of 5-HT release. Anorectic agent; decreases growth hormone, insulin, leptin, fat mass, lean mass and increases ghrelin in diet-switched diet-induced obese mice.

Biochem/physiol Actions

(+)-Fenfluramine is a serotonin uptake inhibitor; anoxexic. (+)-Fenfluramine is neurotoxic on prolonged administration or at high dosage. (+)-Fenfluramine releases serotonin from axon terminals by a nonexocytotic mechanism.

Upstream product

• 21906-39-8 3-(trifluoromethyl)phenylacetone 
• 557-66-4 ethanamine hydrochloride 
• 217320-76-8 (S),(S)-N-ethyl-N-(1-phenylethyl)-α-methyl-3-(trifluoromethyl)benzeneethanamine hydrochloride 
• 108-10-1 4-methyl-2-pentanone 
• 78-93-3 butanone 
• 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.

Method of treating nausea and vomiting with certain substituted-phenylalkylamino (and aminoacid) derivatives and other serotonin depleting agents

A method for the treatment of emesis in a mammal, which method comprises administering to said mammal an emesis inhibiting amount of a compound which depletes serotonin in the brain of mammals; among which are compounds having the formula: STR1 wherein, R is selected from hydrogen, loweralkyl, trifluoromethyl, carboxyl, or loweralkoxycarbonyl; R1 and R2 are hydrogen or loweralkyl; Z is trifluoromethyl or halogen; the optical isomers and pharmaceutically acceptable salts thereof; two of the preferred compounds of the invention are fenfluramine and norfenfluramine.