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CAS

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404-82-0

Fenfluramine hydrochloride, also known as Pondimin, is a crystalline solid that is unique among its group of drugs due to its sedative effects rather than excitatory ones. It is an (±)N-ethyl-α-methyl-3-(trifluoromethyl)phenethylamine hydrochloride, which primarily acts through central serotoninergic mechanisms rather than central noradrenergic ones. Its structure suggests a more apolar or hydrophobic character than amphetamine, indicating a tropism for serotoninergic neurons and an indirect mechanism of action. The increased levels of serotonin lead to greater serotonin receptor activation, which enhances serotoninergic transmission in the hypothalamus, suppressing appetite for carbohydrates. However, it was withdrawn from human use after reports of heart valve damage and pulmonary hypertension.

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  • 404-82-0 Structure

  • Basic information

    1. Product Name: Fenfluramine hydrochloride
    2. 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
    3. CAS NO:404-82-0
    4. Molecular Formula: C12H16F3N*ClH
    5. Molecular Weight: 267.72
    6. EINECS: 206-968-2
    7. Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Amines;Aromatics
    8. Mol File: 404-82-0.mol

  • Chemical Properties

    1. Melting Point: 1660C
    2. Boiling Point: 243.1 °C at 760 mmHg
    3. Flash Point: 100.8 °C
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: 2-8°C
    8. Solubility: N/A
    9. CAS DataBase Reference: Fenfluramine hydrochloride(CAS DataBase Reference)
    10. NIST Chemistry Reference: Fenfluramine hydrochloride(404-82-0)
    11. EPA Substance Registry System: Fenfluramine hydrochloride(404-82-0)

  • Safety Data

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

404-82-0 Usage

Uses

Used in Pharmaceutical Industry:
Fenfluramine hydrochloride was used as an appetite suppressant for the treatment of obesity and diabetes. Its action on serotonin receptors, particularly 5-HT1B and 5-HT2C, led to satiety effects and a preference for lower-fat food intake. However, due to its toxicity and withdrawal from the market, alternative treatments are now sought for these conditions.

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

Check Digit Verification of cas no

The CAS Registry Mumber 404-82-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,0 and 4 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 404-82:
(5*4)+(4*0)+(3*4)+(2*8)+(1*2)=50
50 % 10 = 0
So 404-82-0 is a valid CAS Registry Number.
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

404-82-0Downstream Products

404-82-0Relevant articles and documents

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

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Page/Page column 10-12, (2021/06/22)

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.

NEW METHOD FOR SYNTHESIS OF FENFLURAMINE, AND NEW COMPOSITIONS COMPRISING IT

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Paragraph 0109, (2018/08/09)

A new process for preparing the fenfluramine molecule and new compositions containing fenfluramine obtainable with the claimed process.

FENFLURAMINE COMPOSITIONS AND METHODS OF PREPARING THE SAME

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, (2017/07/14)

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

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, (2008/06/13)

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.