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 Antipsychotics, also known as neuroleptics, are a class of psychotropic medication primarily used to manage psychosis (including delusions, hallucinations, paranoia or disordered thought), principally in schizophrenia but also in a range o ...

and

tranquilizer A tranquilizer is a drug that is designed for the treatment of anxiety, fear, tension, agitation, and disturbances of the mind, specifically to reduce states of anxiety and tension. Etymology Tranquilizer, as a term, was first used by F.F. Yonk ...

which was never marketed. It is a relatively selective antagonist of the serotonin 5-HT₂ receptors and has been used in

scientific research The scientific method is an empirical method for acquiring knowledge that has characterized the development of science since at least the 17th century (with notable practitioners in previous centuries; see the article history of scientific ...

to study the serotonin system. In the 1980s, the drug was found to block the effects of the

lysergic acid diethylamide Lysergic acid diethylamide (LSD), also known colloquially as acid, is a potent psychedelic drug. Effects typically include intensified thoughts, emotions, and sensory perception. At sufficiently high dosages LSD manifests primarily mental, v ...

(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. ...

, 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 prod ...

with

2-Acetylbutyrolactone 2-Acetylbutyrolactone (ABL) is a derivative of γ-butyrolactone that is used as a precursor in organic synthesis, and it is used to identify primary amines through chemical fluorescence. Preparation 2-Acetylbutyrolactone can be prepared by a ...

(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 Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula . It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride. It is manufactured industrially on a large scale from phosp ...

. 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