Perlapine

Perlapine, sold under the brand names Hypnodine and Pipnodine, is a hypnotic and sedative of the tricyclic group which is marketed in Japan.^[1] It acts primarily as a potent antihistamine,^[2] and also has anticholinergic,^[2] antiserotonergic,^[3] antiadrenergic, and some antidopaminergic activity.^[3][4][5][6] The drug has relatively weak affinity for the dopamine D₂ receptor (IC₅₀Tooltip Half-maximal inhibitory concentration = 1,803 nM) and, in accordance, is said to be ineffective as an antipsychotic.^[6][7] However, it retains higher affinity for the dopamine D₁ receptor (IC₅₀ = 198 nM).^[6] Its IC₅₀ values are 19 nM for the α₁-adrenergic receptor, 4,945 nM for the α₂-adrenergic receptor, and 70 nM for the serotonin 5-HT_2A receptor.^[6] Perlapine is closely related to clotiapine, clozapine, fluperlapine, loxapine, and tilozepine.^[6]

Perlapine

Clinical data
Trade names	Hypnodine, Pipnodine
Other names	AW-14233; HF-2333; MP-11; PLP 100-127; 6-(4-Methyl-1-piperazinyl)morphanthridine
Identifiers
IUPAC name 6-(4-Methylpiperazin-1-yl)-11H-benzo[c][1]benzazepine
CAS Number	1977-11-3
PubChem CID	16106
ChemSpider	15291
UNII	4N8UJJ27IM
KEGG	D01438
ChEBI	CHEBI:31983
ChEMBL	ChEMBL340801
CompTox Dashboard (EPA)	DTXSID1048758
ECHA InfoCard	100.241.831
Chemical and physical data
Formula	C19H21N3
Molar mass	291.398 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN1CCN(CC1)C2=NC3=CC=CC=C3CC4=CC=CC=C42
InChI InChI=1S/C19H21N3/c1-21-10-12-22(13-11-21)19-17-8-4-2-6-15(17)14-16-7-3-5-9-18(16)20-19/h2-9H,10-14H2,1H3 Key:PWRPUAKXMQAFCJ-UHFFFAOYSA-N

Perlapine has been suggested as a potential ligand for certain DREADDs.^[8][9]