Flumexadol

Flumexadol
Clinical data
ATC code	None;
Identifiers
	IUPAC name 2-(3-(Trifluoromethyl)phenyl)morpholine;
CAS Number	30914-89-7;
PubChem CID	65774;
ChemSpider	59194;
UNII	V9783UEL0F;
Chemical and physical data
Formula	C11H12F3NO
Molar mass	231.218 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1COC(CN1)C2=CC(=CC=C2)C(F)(F)F;
	InChI 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 code name CERM-1841 or 1841-CERM) is a drug described and researched as a non-opioid analgesic which was never marketed.[1][2][3][4] It has been found to act as an agonist of the serotonin 5-HT_1A (pK_i = 7.1) and 5-HT_2C (pK_i = 7.5) receptors and, to a much lesser extent, of the 5-HT_2A (pK_i = 6.0) receptor.[5][6] According to Nilsson (2006) in a paper on 5-HT_2C receptor agonists as potential anorectics, "The (+)-enantiomer of this compound showed [...] affinity for the 5-HT_2C receptor (K_i) 25 nM) [...] and was 40-fold selective over the 5-HT_2A receptor in receptor binding studies. Curiously, the racemic version [...], also known as 1841 CERM, was originally reported to possess analgesic properties while no association with 5-HT_2C 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 a prodrug of the compound that was formerly used clinically in France as an antidepressant and anxiolytic agent.[5][7][8]

References

J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 561–. ISBN 978-1-4757-2085-3.
Hache J, Diamantis W, Sofia D, Streichenberger G (1978). "The pharmacology of 1841 CERM, a new analgesic". Arzneimittelforschung. 28 (4): 642–5. PMID 312104.
Kucharczyk, N.; Yang, J. T.; Valia, K. H.; Stiefel, F. J.; Sofia, R. D. (1979). "Metabolites of 2-(3-Trifluoromethylphenyl)Tetrahydro-1,4-Oxazine (Cerm 1841) in Rats and Dogs". Xenobiotica. 9 (11): 703–711. doi:10.3109/00498257909042338. ISSN 0049-8254. PMID 532219.
Nilsson, Björn M. (2006). "5-Hydroxytryptamine 2C (5-HT2C) Receptor Agonists as Potential Antiobesity Agents". Journal of Medicinal Chemistry. 49 (14): 4023–4034. doi:10.1021/jm058240i. ISSN 0022-2623. PMID 16821762.
Jean-Pierre Bégué; Daniele Bonnet-Delpon (2 June 2008). Bioorganic and Medicinal Chemistry of Fluorine. John Wiley & Sons. pp. 303–. ISBN 978-0-470-28187-1.
Leysen DC (February 1999). "Selective 5-HT2C agonists as potential antidepressants". IDrugs : The Investigational Drugs Journal. 2 (2): 109–20. PMID 16160946.
J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 909–. ISBN 978-1-4757-2085-3.
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.

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[Elks2014a-1] J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 561–. ISBN 978-1-4757-2085-3.

[pmid312104-2] Hache J, Diamantis W, Sofia D, Streichenberger G (1978). "The pharmacology of 1841 CERM, a new analgesic". Arzneimittelforschung. 28 (4): 642–5. PMID 312104.

[KucharczykYang1979-3] Kucharczyk, N.; Yang, J. T.; Valia, K. H.; Stiefel, F. J.; Sofia, R. D. (1979). "Metabolites of 2-(3-Trifluoromethylphenyl)Tetrahydro-1,4-Oxazine (Cerm 1841) in Rats and Dogs". Xenobiotica. 9 (11): 703–711. doi:10.3109/00498257909042338. ISSN 0049-8254. PMID 532219.

[Nilsson2006-4] Nilsson, Björn M. (2006). "5-Hydroxytryptamine 2C (5-HT2C) Receptor Agonists as Potential Antiobesity Agents". Journal of Medicinal Chemistry. 49 (14): 4023–4034. doi:10.1021/jm058240i. ISSN 0022-2623. PMID 16821762.

[BéguéBonnet-Delpon2008-5] Jean-Pierre Bégué; Daniele Bonnet-Delpon (2 June 2008). Bioorganic and Medicinal Chemistry of Fluorine. John Wiley & Sons. pp. 303–. ISBN 978-0-470-28187-1.

[pmid16160946-6] Leysen DC (February 1999). "Selective 5-HT2C agonists as potential antidepressants". IDrugs : The Investigational Drugs Journal. 2 (2): 109–20. PMID 16160946.

[Elks2014b-7] J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 909–. ISBN 978-1-4757-2085-3.

[isbn3-88763-075-0-8] 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.

Flumexadol

See also

References