1-(1-Naphthyl)piperazine

Chemical compound 1-(naphthalen-1-yl)piperazine Naphthylpiperazine.png skin-invert-image 125px Skeletal formula of naphthylpiperazine Naphthylpiperazine-3D-balls.png bg-transparent 140 Ball-and-stick model of the naphthylpiperazine molecule Uncontrolled Oral correct CAS 57536-86-4 correct FDA FJ7MR37A24 none 1342 3 1302 14 16 2 c2cc(c1ccccc1c2)N3CCNCC3 1-(1-Naphthyl)piperazine (1-NP) is a drug which is a phenylpiperazine derivative. It acts as a non-selective, mixed serotonergic agent, exerting partial agonism at the 5-HT1A, 5-HT1B, 5-HT1D, 5-HT1E, and 5-HT1F receptors,Schoeffter P, Hoyer D Interaction of arylpiperazines with 5-HT1A, 5-HT1B, 5-HT1C and 5-HT1D receptors: do discriminatory 5-HT1B receptor ligands exist? Naunyn-Schmiedeberg's Archives of Pharmacology 339 6 675–83 June 1989 2770889 10.1007/bf00168661 42399446 Bai F, Yin T, Johnstone EM, etal Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor European Journal of Pharmacology 484 2–3 127–39 January 2004 14744596 10.1016/j.ejphar.2003.11.019Adham N, Kao HT, Schecter LE, etal Cloning of another human serotonin receptor (5-HT1F): a fifth 5-HT1 receptor subtype coupled to the inhibition of adenylate cyclase Proceedings of the National Academy of Sciences of the United States of America 90 2 408–12 January 1993 8380639 45671 10.1073/pnas.90.2.408 1993PNAS...90..408A free while antagonizing the 5-HT2A, 5-HT2B, and 5-HT2C receptors.Conn PJ, Sanders-Bush E Relative efficacies of piperazines at the phosphoinositide hydrolysis-linked serotonergic (5-HT-2 and 5-HT-1c) receptors The Journal of Pharmacology and Experimental Therapeutics 242 2 552–7 August 1987 3039120 http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=3039120McKune CM, Watts SW Characterization of the serotonin receptor mediating contraction in the mouse thoracic aorta and signal pathway coupling The Journal of Pharmacology and Experimental Therapeutics 297 1 88–95 April 2001 11259531 http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=11259531Kursar JD, Nelson DL, Wainscott DB, Baez M Molecular cloning, functional expression, and mRNA tissue distribution of the human 5-hydroxytryptamine2B receptor Molecular Pharmacology 46 2 227–34 August 1994 8078486 http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=8078486 It has also been shown to possess high affinity for the 5-HT3, 5-HT5A, 5-HT6, and 5-HT7 receptors,Glennon RA, Ismaiel AE, McCarthy BG, Peroutka SJ Binding of arylpiperazines to 5-HT3 serotonin receptors: results of a structure-affinity study European Journal of Pharmacology 168 3 387–92 September 1989 2583244 10.1016/0014-2999(89)90802-9 Wesołowska A In the search for selective ligands of 5-HT5, 5-HT6 and 5-HT7 serotonin receptors Polish Journal of Pharmacology 54 4 327–41 2002 12523486 Lee M, Rangisetty JB, Pullagurla MR, etal 1-(1-Naphthyl)piperazine as a novel template for 5-HT6 serotonin receptor ligands Bioorganic & Medicinal Chemistry Letters 15 6 1707–11 March 2005 15745826 10.1016/j.bmcl.2005.01.031 Bard JA, Zgombick J, Adham N, Vaysse P, Branchek TA, Weinshank RL Cloning of a novel human serotonin receptor (5-HT7) positively linked to adenylate cyclase The Journal of Biological Chemistry 268 31 23422–6 November 1993 10.1016/S0021-9258(19)49479-9 8226867 http://www.jbc.org/cgi/pmidlookup?view=long&pmid=8226867 free January 2026 InternetArchiveBot and may bind to 5-HT4 and the SERT as well.Curtet S, Soulier JL, Zahradnik I, etal New arylpiperazine derivatives as antagonists of the human cloned 5-HT(4) receptor isoforms Journal of Medicinal Chemistry 43 20 3761–9 October 2000 11020291 10.1021/jm0009538 https://hal-universite-paris-saclay.archives-ouvertes.fr/hal-03611715/file/Version%20HAL.pdf Perrone R, Berardi F, Colabufo NA, etal Design and synthesis of long-chain arylpiperazines with mixed affinity for serotonin transporter (SERT) and 5-HT(1A) receptor The Journal of Pharmacy and Pharmacology 57 10 1319–27 October 2005 16259761 10.1211/jpp.57.10.0011 84457274 http://openurl.ingenta.com/content/nlm?genre=article&issn=0022-3573&volume=57&issue=10&spage=1319&aulast=Perrone subscription In animals it produces effects including hyperphagia,Kennett GA, Curzon G Evidence that hypophagia induced by mCPP and TFMPP requires 5-HT1C and 5-HT1B receptors; hypophagia induced by RU 24969 only requires 5-HT1B receptors Psychopharmacology 96 1 93–100 1988 2906446 10.1007/BF02431539 21417374 Gibson EL, Kennedy AJ, Curzon G d-Fenfluramine- and d-norfenfluramine-induced hypophagia: differential mechanisms and involvement of postsynaptic 5-HT receptors European Journal of Pharmacology 242 1 83–90 September 1993 8223940 10.1016/0014-2999(93)90013-8Schechter LE, Simansky KJ 1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane (DOI) exerts an anorexic action that is blocked by 5-HT2 antagonists in rats Psychopharmacology 94 3 342–6 1988 3128809 10.1007/bf00174687 6463496 hyperactivity,Perveen T, Rafiq R, Haider S, Haleem DJ Increased serotonergic functions following administration of 1-(1-naphthyl) piperazine in propranolol injected rats Pakistan Journal of Pharmaceutical Sciences 19 3 194 July 2006 16935825 Kennett GA 5-HT1C receptor antagonists have anxiolytic-like actions in the rat social interaction model Psychopharmacology 107 2–3 379–84 1992 1352056 10.1007/BF02245165 44041403 and anxiolysis,Pruus K, Rudisaar R, Vaarmann A, Matto V, Allikmets L 1-(1-naphthyl)-piperazine, a mixed 5-HT1A and 5-HT2A/2C receptor ligand, elicits an anxiolytic-like effect in the open-field test without changes in 5-HT metabolism Methods and Findings in Experimental and Clinical Pharmacology 24 3 151–7 April 2002 12087877 10.1358/mf.2002.24.3.802300 http://journals.prous.com/journals/servlet/xmlxsl/pk_journals.xml_summaryn_pr?p_JournalId=6&p_RefId=802300 subscription Gibson EL, Barnfield AM, Curzon G Evidence that mCPP-induced anxiety in the plus-maze is mediated by postsynaptic 5-HT2C receptors but not by sympathomimetic effects Neuropharmacology 33 3–4 457–65 1994 7984284 10.1016/0028-3908(94)90076-0 3029085 free Kennett GA, Pittaway K, Blackburn TP Evidence that 5-HT2c receptor antagonists are anxiolytic in the rat Geller-Seifter model of anxiety Psychopharmacology 114 1 90–6 February 1994 7846211 10.1007/BF02245448 12720128 of which are all likely mediated predominantly or fully by blockade of the 5-HT2C receptor. Derivatives of naphthylpiperazine include CSP-2503, F-11,461, S-14506, and S-14671. See also 1-(2-Naphthyl)piperazine (2-NP) Substituted piperazine Diphenylpiperazine Phenylpiperazine Quipazine References Category:1-(1-Naphthyl)piperazines Category:Serotonin receptor antagonists Category:Serotonin receptor agonists