Perlapine

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

References

^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 811–. ISBN 978-3-88763-075-1.
^ ^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.
^ ^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.
^ Hathway DE (31 October 2007). Foreign Compound Metabolism in Mammals. Royal Society of Chemistry. pp. 302–. ISBN 978-1-84755-608-0.
^ 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.
^ ^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.
^ American College of Neuropsychopharmacology (1978). Psychopharmacology: a generation of progress. Raven Press. p. 514. ISBN 978-0-89004-191-8.
^ 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.
^ 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.

This sedative-related article is a stub. You can help Wikipedia by expanding it.

[IndexNominum2000-1] Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 811–. ISBN 978-3-88763-075-1.

[Lajtha2013-2] 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.

[Megens_1996-3] 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.

[Hathway2007-4] Hathway DE (31 October 2007). Foreign Compound Metabolism in Mammals. Royal Society of Chemistry. pp. 302–. ISBN 978-1-84755-608-0.

[Publishers1995-5] 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.

[Barnes2013-6] Barnes TR (22 October 2013). Antipsychotic Drugs and Their Side-Effects. Elsevier Science. pp. 28, 34. ISBN 978-1-4832-8810-9.

[Neuropsychopharmacology1978-7] 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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]