Pirenperone

Pirenperone
Clinical data
Other names	R-47456; R-50656; Pirenpirone
Identifiers
	IUPAC name 3-[2-[4-(4-Fluorobenzoyl)piperidin-1-yl]ethyl]-2-methylpyrido[1,2-a]pyrimidin-4-one;
CAS Number	75444-65-4;
PubChem CID	4847;
ChemSpider	4681;
UNII	Y9FMC4513X;
KEGG	D05495;
ChEBI	CHEBI:92444;
ChEMBL	ChEMBL18331;
CompTox Dashboard (EPA)	DTXSID9045182 ;
ECHA InfoCard	100.071.081
Chemical and physical data
Formula	C23H24FN3O2
Molar mass	393.462 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C(C(=O)N2C=CC=CC2=N1)CCN3CCC(CC3)C(=O)C4=CC=C(C=C4)F;
	InChI InChI=1S/C23H24FN3O2/c1-16-20(23(29)27-12-3-2-4-21(27)25-16)11-15-26-13-9-18(10-14-26)22(28)17-5-7-19(24)8-6-17/h2-8,12,18H,9-11,13-15H2,1H3; Key:HXCNRYXBZNHDNE-UHFFFAOYSA-N;

Pirenperone (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, BANTooltip British Approved Name; developmental code names R-47456, R-50656) is a serotonin receptor antagonist closely related to ketanserin and risperidone which is described as an antipsychotic and tranquilizer and was never marketed.^[1]^[2]

Quick Facts Clinical data, Other names ...

It is a relatively selective antagonist of the serotonin 5-HT_2A receptor and has been used in scientific research to study the serotonin system.^[3]^[2]^[4]^[5] Its affinities (K_i) for serotonin and other receptors have been reported to be 0.3 to 1.1 nM for the serotonin 5-HT_2A receptor, 6.5 nM for the serotonin 5-HT₇ receptor, 20 nM for the α_1B-adrenergic receptor, 20 nM for the α_2B-adrenergic receptor, 61 nM for the serotonin 5-HT_2B receptor, 60 to 77 nM for the serotonin 5-HT_2C receptor, 485 to 1,700 nM for the serotonin 5-HT_1A receptor, and >1,000 or 6,600 nM for the serotonin 5-HT_1B receptor, whereas other receptors were not reported.^[3]^[5]

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-HT_2A receptor as the biological mediator of the effects of serotonergic psychedelics.^[6]

See also