Pirenperone (, , ; developmental code names R-47456, R-50656) is a

serotonin receptor antagonist A serotonin antagonist, or serotonin receptor antagonist, is a drug used to inhibit the action at serotonin (5-HT) receptors. Types 5-HT2A antagonists Antagonists of the 5-HT2A receptor are sometimes used as atypical antipsychotics (contrast wi ...

described as an antipsychotic and tranquilizer which was never marketed. It is a relatively selective

antagonist An antagonist is a character in a story who is presented as the chief foe of the protagonist. Etymology The English word antagonist comes from the Greek ἀνταγωνιστής – ''antagonistēs'', "opponent, competitor, villain, enemy, riv ...

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-HT₂ receptors and has been used in scientific research to study the

system. In the 1980s, the drug was found to block the effects of the lysergic acid diethylamide (LSD) in animals, and along with

ketanserin Ketanserin (INN, USAN, BAN) (brand name Sufrexal; former developmental code name R41468) is a drug used clinically as an antihypertensive agent and in scientific research to study the serotonin system; specifically, the 5-HT2 receptor family. I ...

, led to the elucidation of the 5-HT_2A receptor as the biological mediator of the effects of serotonergic psychedelics.

Synthesis

The sidechain is formed from the cyclization of

2-aminopyridine 2-Aminopyridine is an organic compound with the formula H2NC5H4N. It is one of three isomeric aminopyridines. It is a colourless solid that is used in the production of the drugs piroxicam, sulfapyridine, tenoxicam, and tripelennamine. It is pr ...

with 2-Acetylbutyrolactone (2) in PPA gave 3-(2-hydroxyethyl)-2-methylpyrido

,2-a The comma is a punctuation mark that appears in several variants in different languages. It has the same shape as an apostrophe or single closing quotation mark () in many typefaces, but it differs from them in being placed on the baseline o ...

yrimidin-4-one 1078-67-5(3). Halogenation replaces the hydroxy with the chloride leaving group. Many syntheses do both steps in one-pot with phosphorus oxychloride. The

4-(4-Fluorobenzoyl)Piperidine A coxless four is a rowing boat used in the sport of competitive rowing. It is designed for four persons who propel the boat with sweep oars, without a coxswain. The crew consists of four rowers, each having one oar. There are two rowers on th ...

6346-57-7has 12 known named uses. Pirenperone synthesis

The alkylation between 3-(2-chloroethyl)-2-methylpyrido

yrimidin-4-one 1078-70-0(1) and 4-(4-fluorobenzoyl)piperidine hydrochloride 5519-78-2(2) afforded pirenperone (3).

References

5-HT2 antagonists Antipsychotics Anxiolytics Fluoroarenes Ketones Piperidines Pyridopyrimidines {{Nervous-system-drug-stub

Synthesis

See also

References