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 (IC₅₀ = 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

References

1. Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 811–. ISBN 978-3-88763-075-1.
2. Leysen JE, Niemegeers CJ (1985). "Neuroleptics". In Lajtha A (ed.). Alterations of Metabolites in the Nervous System. Boston, MA.: Springer Science & Business Media. pp. 331–361. ISBN 978-1-4757-6740-7.
3. Megens AA, Kennis LE (1996). "Risperidone and related 5HT2/D2 antagonists: a new type of antipsychotic agent?". Progress in Medicinal Chemistry. 33: 185–232. doi:10.1016/s0079-6468(08)70306-0. ISBN 9780444823106. PMID 8776944.
4. Hathway DE (31 October 2007). Foreign Compound Metabolism in Mammals. Royal Society of Chemistry. pp. 302–. ISBN 978-1-84755-608-0.
5. Liegeois JF, Bruhwyler J, Rogister F, Delarge J (April 1995). "Diarylazepine derivatives as potent atypical neuroleptic drugs: recent advances". Current Medicinal Chemistry. Bentham Science Publishers. 1 (6): 471–501.
6. Barnes TR (22 October 2013). Antipsychotic Drugs and Their Side-Effects. Elsevier Science. pp. 28, 34. ISBN 978-1-4832-8810-9.
7. American College of Neuropsychopharmacology (1978). Psychopharmacology: a generation of progress. Raven Press. p. 514. ISBN 978-0-89004-191-8.