Flumexadol (; developmental codes CERM-1841 and 1841-CERM) is a serotonin receptor modulator which was described and researched as a non-opioid analgesic but was never marketed. It might be employable as an anorectic in addition to analgesic. 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.
Pharmacology Pharmacodynamics Flumexadol has been found to act as an agonist of the serotonin 5-HT1A receptor (Ki = 79nM), of the serotonin 5-HT2C receptor (Ki = 32nM), and, to a much lesser extent, of the serotonin 5-HT2A receptor (Ki = 1,000nM). According to Nilsson (2006) in a paper on serotonin 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."
Chemistry 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).
See also Oxaflozane Befiradol Fenfluramine Fludorex Fluminorex TFMPP
References
External links Flumexadol - Isomer Design