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

dl-fenfluramine hydrochloride

C₂₁H₂₄F₃NO₄

Refernces

• 1、 -. "FENFLURAMINE COMPOSITIONS AND METHODS OF PREPARING THE SAME". Paragraph 0104; 0106; 0107; 0119; 0120. . Retrieved 2017/07/14.
• 2、 Goument, B.,Duhamel, L.,Mauge, R.. "Syntheses of (S)-fenfluramine from (R) or (S)-1-propan-2-ol". . p. 450 - 458. Retrieved 2007/10/02.