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Perlapine
Clinical data
Trade namesHypnodine, Pipnodine
Other namesAW-14233; HF-2333; MP-11; PLP 100-127; 6-(4-Methyl-1-piperazinyl)morphanthridine
Identifiers
  • 6-(4-Methylpiperazin-1-yl)-11H-benzo[c][1]benzazepine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard ( EPA)
ECHA InfoCard 100.241.831 Edit this at Wikidata
Chemical and physical data
FormulaC19H21N3
Molar mass291.398 g·mol−1
3D model ( JSmol)
  • CN1CCN(CC1)C2=NC3=CC=CC=C3CC4=CC=CC=C42
  • 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, 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]

References

  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.


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