Flumexadol
Chemical compound
From Wikipedia, the free encyclopedia
Flumexadol (INN; 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.[1][2][3][4] It 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][6][7]
- None
| |
| Clinical data | |
|---|---|
| Drug class | Serotonin 5-HT1A receptor agonist; Serotonin 5-HT2C receptor agonist; Serotonin 5-HT2A receptor agonist |
| ATC code |
|
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C11H12F3NO |
| Molar mass | 231.218 g·molâ1 |
| 3D model (JSmol) | |
| |
| |
Pharmacology
Pharmacodynamics
Flumexadol has been found to act as an agonist of the serotonin 5-HT1A receptor (Ki = 79 nM), of the serotonin 5-HT2C receptor (Ki = 32 nM), and, to a much lesser extent, of the serotonin 5-HT2A receptor (Ki = 1,000 nM).[5][8] 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."[4]
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).