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Clinical data
Trade namesHypnodine, Pipnodine
Other namesAW-14233; HF-2333; MP-11; PLP 100-127; 6-(4-Methyl-1-piperazinyl)morphanthridine
  • 6-(4-Methylpiperazin-1-yl)-11H-benzo[c][1]benzazepine
CAS Number
PubChem CID
CompTox Dashboard (EPA)
ECHA InfoCard100.241.831 Edit this at Wikidata
Chemical and physical data
Molar mass291.398 g·mol−1
3D model (JSmol)
  • 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

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-HT2A receptor.[6] Perlapine is closely related to clotiapine, clozapine, fluperlapine, loxapine, and tilozepine.[6]

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


  1. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 811–. ISBN 978-3-88763-075-1.
  2. ^ a b 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. ^ a b 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. 1 (6). Bentham Science Publishers: 471–501. doi:10.2174/092986730106220216114910. S2CID 87829622.
  6. ^ a b c d e 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.
  8. ^ Thompson KJ, Khajehali E, Bradley SJ, Navarrete JS, Huang XP, Slocum S, et al. (September 2018). "DREADD Agonist 21 Is an Effective Agonist for Muscarinic-Based DREADDs in Vitro and in Vivo". ACS Pharmacology & Translational Science. 1 (1): 61–72. doi:10.1021/acsptsci.8b00012. PMC 6407913. PMID 30868140.
  9. ^ Chen X, Choo H, Huang XP, Yang X, Stone O, Roth BL, Jin J (March 2015). "The first structure-activity relationship studies for designer receptors exclusively activated by designer drugs". ACS Chemical Neuroscience. 6 (3): 476–484. doi:10.1021/cn500325v. PMC 4368042. PMID 25587888.