Flumexadol ( INN) (developmental code name CERM-1841 or 1841-CERM) is a

drug A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via insuffla ...

described and researched as a non- opioid

analgesic An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...

which was never marketed. It has been found to act as an

agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...

of the

serotonin Serotonin () or 5-hydroxytryptamine (5-HT) is a monoamine neurotransmitter. Its biological function is complex and multifaceted, modulating mood, cognition, reward, learning, memory, and numerous physiological processes such as vomiting and vas ...

5-HT_1A (pK_i = 7.1) and 5-HT_2C (pK_i = 7.5)

receptor Receptor may refer to: * Sensory receptor, in physiology, any structure which, on receiving environmental stimuli, produces an informative nerve impulse *Receptor (biochemistry), in biochemistry, a protein molecule that receives and responds to a ...

s 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 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." 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 Oxaflozane ( INN) (brand name Conflictan) is an antidepressant and anxiolytic drug that was introduced by Solvay in France in 1982 for the treatment of depression but has since been discontinued. It is a prodrug of flumexadol (''N''-dealkyloxaf ...

(brand name Conflictan) is a

prodrug A prodrug is a medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug ...

of the compound that was formerly used clinically in France as an

antidepressant Antidepressants are a class of medication used to treat major depressive disorder, anxiety disorders, chronic pain conditions, and to help manage addictions. Common side-effects of antidepressants include dry mouth, weight gain, dizziness, hea ...

and anxiolytic 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 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