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Flumexadol

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Flumexadol
Clinical data
ATC code
  • None
Identifiers
  • 2-(3-(Trifluoromethyl)phenyl)morpholine
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC11H12F3NO
Molar mass231.218 g·mol−1
3D model (JSmol)
  • C1COC(CN1)C2=CC(=CC=C2)C(F)(F)F
  • InChI=1S/C11H12F3NO/c12-11(13,14)9-3-1-2-8(6-9)10-7-15-4-5-16-10/h1-3,6,10,15H,4-5,7H2
  • Key:GXPYCYWPUGKQIJ-UHFFFAOYSA-N

Flumexadol (INN; developmental codesCERM-1841 and1841-CERM) is adrug described and researched as a non-opioidanalgesic which was never marketed.[1][2][3][4] It has been found to act as anagonist of theserotonin5-HT1A (pKi = 7.1) and5-HT2C (pKi = 7.5)receptors and, to a much lesser extent, of the5-HT2A (pKi = 6.0) receptor.[5][6] According to Nilsson (2006) in a paper on 5-HT2C receptor agonists as potentialanorectics, "The (+)-enantiomer of this compound showed [...] affinity for the 5-HT2C receptor (Ki) 25 nM) [...] and was 40-fold selective over the 5-HT2A receptor in receptor binding studies. The racemic version [...], also known as 1841 CERM, was originally reported to possess analgesic properties while no association with 5-HT2C receptor activity was mentioned."[4] It is implied that flumexadol might be employable as an anorectic in addition to analgesic.[4] Though flumexadol itself has never been approved for medical use,oxaflozane (brand name Conflictan) is aprodrug of the compound that was formerly used clinically inFrance as anantidepressant andanxiolytic agent.[5][7][8]

Synthesis

[edit]
Thieme Synthesis:[9] Patent:[10]

Halogenation of 2-chloroethyl vinyl ether (1) with molecular bromine gives 1,2-dibromo-1-(2-chloroethoxy)ethane (2).Grignard reaction with 3-bromobenzotrifluoride (3) gives 1-[2-bromo-1-(2-chloroethoxy)ethyl]-3-(trifluoromethyl)benzene (4). Treatment with benzylamine gives 4-benzyl-2-[3-(trifluoromethyl) phenyl]morpholine (5).Catalytic hydrogenation strips the benzylprotecting group completing the synthesis of flumexadol (6).

See also

[edit]

References

[edit]
  1. ^Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 561–.ISBN 978-1-4757-2085-3.
  2. ^Hache J, Diamantis W, Sofia D, Streichenberger G (1978). "The pharmacology of 1841 CERM, a new analgesic".Arzneimittel-Forschung.28 (4):642–645.PMID 312104.
  3. ^Kucharczyk N, Yang JT, Valia KH, Stiefel FJ, Sofia RD (November 1979). "Metabolites of 2-(3-trifluoromethylphenyl)tetrahydro-1,4-oxazine (CERM) 1841) in rats and dogs".Xenobiotica; the Fate of Foreign Compounds in Biological Systems.9 (11):703–711.doi:10.3109/00498257909042338.PMID 532219.
  4. ^abcNilsson BM (July 2006). "5-Hydroxytryptamine 2C (5-HT2C) receptor agonists as potential antiobesity agents".Journal of Medicinal Chemistry.49 (14):4023–4034.doi:10.1021/jm058240i.PMID 16821762.
  5. ^abBégué JP, Bonnet-Delpon D (2 June 2008).Bioorganic and Medicinal Chemistry of Fluorine. John Wiley & Sons. pp. 303–.ISBN 978-0-470-28187-1.
  6. ^Leysen DC (February 1999). "Selective 5-HT2C agonists as potential antidepressants".IDrugs.2 (2):109–120.PMID 16160946.
  7. ^Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 909–.ISBN 978-1-4757-2085-3.
  8. ^Swiss Pharmaceutical Society (2000).Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. p. 766.ISBN 3-88763-075-0.
  9. ^Busch N, Moleyre J, Simond J, Bondivenne R, Labrid C (1976). "Tetrahydro-1, 4-Oxazines. I. New Synthesis Method and a Study of Their Interaction With Tryptaminergic D Receptors".European Journal of Medicinal Chemistry.11:201–207.
  10. ^FR 95182, "Process for the synthesis of 2-4-disubstituted tetrahydro 1,4-oxazines", assigned to Centre Europeen de Recherches Mauvernay CERM 
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
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