Flumexadol (

INN Inns are generally establishments or buildings where travelers can seek lodging, and usually, food and drink. Inns are typically located in the country or along a highway; before the advent of motorized transportation they also provided accommo ...

) (developmental code name CERM-1841 or 1841-CERM) is a drug described and researched as a non-

opioid Opioids are substances that act on opioid receptors to produce morphine-like effects. Medically they are primarily used for pain relief, including anesthesia. Other medical uses include suppression of diarrhea, replacement therapy for opioid use ...

analgesic which was never marketed. 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. According to Nilsson (2006) in a paper on 5-HT_2C receptor agonists as potential

anorectic An anorectic or anorexic is a drug which reduces appetite, resulting in lower food consumption, leading to weight loss. By contrast, an appetite stimulant is referred to as orexigenic. The term is (from the Greek ''ἀν-'' (an-) = "without" a ...

s, "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." It is implied that flumexadol 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 France (), officially the French Republic ( ), is a country primarily located in Western Europe. It also comprises of overseas regions and territories in the Americas and the Atlantic, Pacific and Indian Oceans. Its metropolitan area ...

as an antidepressant and

anxiolytic An anxiolytic (; also antipanic or antianxiety agent) is a medication or other intervention that reduces anxiety. This effect is in contrast to anxiogenic agents which increase anxiety. Anxiolytic medications are used for the treatment of anxiet ...

agent.

Synthesis

Ex 1: Halogenation of 2-chloro ethyl vinyl ether 10-75-8(1) with molecular bromine gives 1,2-dibromo-1-(2-chloroethoxy)ethane 4689-94-2(2).

Grignard reaction The Grignard reaction () is an organometallic chemical reaction in which alkyl, allyl, vinyl, or aryl-magnesium halides (Grignard reagent) is added to a carbonyl group in an aldehyde or ketone. This reaction is important for the formation of ...

with 3-bromobenzotrifluoride 01-78-5(3) gives 1- -Bromo-1-(2-chloroethoxy)ethyl3-(trifluoromethyl)benzene
CID:12343529
(4). Ex 4: Treatment with benzylamine gives 4-benzyl-2- -(trifluoromethyl) phenylorpholine
CID:213531
(5). Ex 6: Catalytric hydrogenation strips the benzyl protecting group completing the synthesis of flumexadol (6).

References

5-HT1A agonists 5-HT2A agonists 5-HT2C agonists Analgesics Anorectics Antidepressants Anxiolytics Phenylmorpholines Trifluoromethyl compounds {{analgesic-stub

Synthesis

See also

References