Fenfluramine

Base Information

• Chemical Name: Fenfluramine
• CAS No.: 458-24-2
• Deprecated CAS: 5220-89-3,25990-46-9
• Molecular Formula: C₁₂H₁₆F₃N
• Molecular Weight: 231.261
• European Community (EC) Number: 206-968-2,207-276-3
• UNII: 2DS058H2CF
• DSSTox Substance ID: DTXSID4023044
• Nikkaji Number: J5.760F
• Wikipedia: Fenfluramine
• Wikidata: Q418928
• NCI Thesaurus Code: C81418
• RXCUI: 4328
• Metabolomics Workbench ID: 143595
• ChEMBL ID: CHEMBL87493
• Mol file: 458-24-2.mol

Synonyms:Fenfluramine;Fenfluramine Hydrochloride;Fenfluramine Hydrochloride, (+-)-Isomer;Fenfluramine Hydrochloride, R Isomer;Fenfluramine Hydrochloride, R-Isomer;Fenfluramine, (+-)-Isomer;Fenfluramine, R Isomer;Fenfluramine, R-Isomer;Fintepla;Hydrochloride, Fenfluramine;Isomeride;Pondimin

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Fenfluramine

Chemical Property:

• Melting Point: 170°C
• Boiling Point: 243.1 ºC at 760 mmHg
• PKA: pKa 9.10 (Uncertain)
• Flash Point: 100.8 ºC
• PSA: 12.03000
• Density: 1.078 g/cm³
• LogP: 3.63680
• Storage Temp.: ?20°C
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 231.12348400
• Heavy Atom Count: 16
• Complexity: 203

Purity/Quality:

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45

MSDS Files:

Useful:

• Canonical SMILES: CCNC(C)CC1=CC(=CC=C1)C(F)(F)F
• Recent ClinicalTrials: A Study to Investigate the Long-Term Safety of ZX008 (Fenfluramine Hydrochloride) Oral Solution in Children and Adults With Epileptic Encephalopathy Including Dravet Syndrome and Lennox-Gastaut Syndrome
• Recent EU Clinical Trials: A PHASE 3, RANDOMIZED, DOUBLE-BLIND, PLACEBOCONTROLLED, FIXED-DOSE, MULTICENTER STUDY TO EXAMINE THE EFFICACY AND SAFETY OF ZX008 IN SUBJECTS WITH CDKL5 DEFICIENCY DISORDER FOLLOWED BY AN OPEN-LABEL EXTENSION
• Uses: Anorexic.
• Therapeutic Function: Anorexic

Technology Process of Fenfluramine

There total 28 articles about Fenfluramine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.3%

3-(trifluoromethyl)phenylacetone (21906-39-8) + ethylamine (75-04-7,85404-22-4) → Fenfluramine (458-24-2,3239-44-9,5220-89-3,37577-24-5)

Guidance literature:

With sodium tris(acetoxy)borohydride; In methanol; water; at 25 ℃; for 16h; Temperature;

Reference yield:

3-(trifluoromethyl)phenylacetone (21906-39-8) + ethanamine hydrochloride (557-66-4) → Fenfluramine (458-24-2,3239-44-9,5220-89-3,37577-24-5)

Guidance literature:

3-(trifluoromethyl)phenylacetone; ethanamine hydrochloride; With sodium hydroxide; In methanol; at 20 ℃; for 4.5h;

With sodium tetrahydroborate; water; In methanol; at 0 - 20 ℃; for 2h; Temperature; Reagent/catalyst; Solvent; Time;

Reference yield:

1-ethyl-2-<3-(trifluoromethyl)benzyl>aziridine (59287-43-3) → Fenfluramine (458-24-2,3239-44-9,5220-89-3,37577-24-5) + Diethyl-[1-methyl-2-(3-trifluoromethyl-phenyl)-ethyl]-amine

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 19 ℃; for 16h; under 750.06 Torr; Yield given. Yields of byproduct given;

upstream raw materials:

diethyl sulfate

<1-methyl-2-(3-phenyl)ethyl>phosphoramidate de diethyle

ethanol

1-ethyl-2-<3-(trifluoromethyl)benzyl>aziridine

Downstream raw materials:

C₁₉H₂₀F₃NO₂

N-idrossifenfluramina

C₂₁H₂₄F₃NO₄

Refernces

The structure of nitrones derived from amphetamines

10.1111/j.2042-7158.1974.tb09281.x

The research investigates the structure of nitrones derived from amphetamines, specifically focusing on the major in vitro metabolic product of fenfluramine. Initially, the authors identified the major metabolic product as a nitrone, deducing its structure based on its reduction to N-hydroxyfenfluramine and subsequent regeneration using lithium aluminium hydride and yellow mercuric oxide. They initially proposed structure IIa for this nitrone but later revised it to IIIa after further studies and mass spectral evidence suggested that structures IIa and IIIa could not be differentiated by mass spectral data alone. The authors used various chemicals in their research, including N-hydroxy-N-n-propylamphetamine, N-ethyl-N-hydroxyamphetamine, yellow mercuric oxide, lithium aluminium hydride, and m-chloroperbenzoic acid. They also employed techniques such as gas chromatography, nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry to analyze and confirm the structures of the nitrones. The study ultimately concluded that nitrones of general structure III are the major and likely exclusive initial products of mild oxidation of N-alkyl-N-hydroxyamphetamines, and these nitrones are more stable than previously suggested.