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Flumexadol
Chemical compound From Wikipedia, the free encyclopedia
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Flumexadol (INN; developmental codes CERM-1841 and 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-HT1A (pKi = 7.1) and 5-HT2C (pKi = 7.5) receptors and, to a much lesser extent, of the 5-HT2A (pKi = 6.0) receptor.[5][6] According to Nilsson (2006) in a paper on 5-HT2C receptor agonists as potential anorectics, "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 a prodrug of the compound that was formerly used clinically in France as an antidepressant and anxiolytic agent.[5][7][8]
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Synthesis
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 benzyl protecting group completing the synthesis of flumexadol (6).
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See also
References
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