|Other names||R-47456; R-50656|
|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||393.462 g·mol−1|
|3D model (JSmol)|
Pirenperone (INN, USAN, BAN; developmental code names R-47456, R-50656) is a serotonin receptor antagonist described as an antipsychotic and tranquilizer which was never marketed. It is a relatively selective antagonist of the serotonin 5-HT2 receptors and has been used in scientific research to study the serotonin system. In the 1980s, the drug was found to block the effects of the lysergic acid diethylamide (LSD) in animals, and along with ketanserin, led to the elucidation of the 5-HT2A receptor as the biological mediator of the effects of serotonergic psychedelics.
The sidechain is formed from the cyclization of 2-aminopyridine with 2-Acetylbutyrolactone (2) in PPA gave 3-(2-hydroxyethyl)-2-methylpyrido[1,2-a]pyrimidin-4-one [41078-67-5] (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 [56346-57-7] has 12 known named uses.
The alkylation between 3-(2-chloroethyl)-2-methylpyrido[1,2-a]pyrimidin-4-one [41078-70-0] (1) and 4-(4-fluorobenzoyl)piperidine hydrochloride [25519-78-2] (2) afforded pirenperone (3).
- J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 994–. ISBN 978-1-4757-2085-3.
- I.K. Morton; Judith M. Hall (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 223–. ISBN 978-0-7514-0499-9.
- Francis C. Colpaert; Robert Balster (6 December 2012). Transduction Mechanisms of Drug Stimuli. Springer Science & Business Media. pp. 29–. ISBN 978-3-642-73223-2.
- Nichols DE (2016). "Psychedelics". Pharmacol. Rev. 68 (2): 264–355. doi:10.1124/pr.115.011478. PMC 4813425. PMID 26841800.
- EP0037265 idem Ludo E. J. Kennis, Josephus C. Mertens; U.S. Patent 4,342,870 (1982 to Janssen Pharmaceutica N.V.).