2,3-Dichlorophenylpiperazine

DCPP changed changed 477210276 Dichlorophenylpiperazine.svg skin-invert-image 1-(2,3-Dichlorophenyl)piperazine 1/C10H12Cl2N2/c11-8-2-1-3-9(10(8)12)14-6-4-13-5-7-14/h1-3,13H,4-7H2 UDQMXYJSNNCRAS-UHFFFAOYAH UDQMXYJSNNCRAS-UHFFFAOYAH correct CAS 41202-77-1 correct FDA 891W3EV0B1 851833 correct chemspider correct chemspider 1S/C10H12Cl2N2/c11-8-2-1-3-9(10(8)12)14-6-4-13-5-7-14/h1-3,13H,4-7H2 correct chemspider UDQMXYJSNNCRAS-UHFFFAOYSA-N 744460 Clc1c(Cl)c(ccc1)N2CCNCC2 1S/C10H12Cl2N2/c11-8-2-1-3-9(10(8)12)14-6-4-13-5-7-14/h1-3,13H,4-7H2 C10H12Cl2N2 231.12 g/mol brown oil 1.272g/cm3 °C 242 to 244 365.1 at 760mmHg 174.6 2,3-Dichlorophenylpiperazine (2,3-DCPP or DCPP) is a chemical compound from the phenylpiperazine family. It is both a precursor in the synthesis of aripiprazole and one of its metabolites. Leś A, Badowska-Rosłonek K, Łaszcz M, Kamieńska-Duda A, Baran P, Kaczmarek Ł Optimization of aripiprazole synthesis Acta Poloniae Pharmaceutica 67 2 151–7 2010 20369792 Caccia S N-dealkylation of arylpiperazine derivatives: disposition and metabolism of the 1-aryl-piperazines formed Current Drug Metabolism 8 6 612–22 August 2007 17691920 10.2174/138920007781368908 It is unclear whether 2,3-DCPP is pharmacologically active as a serotonin receptor agonist similar to its close analogue 3-chlorophenylpiperazine (mCPP), though it has been shown to act as a partial agonist of the dopamine D2 and D3 receptors. Newman AH, Beuming T, Banala AK, Donthamsetti P, Pongetti K, LaBounty A, Levy B, Cao J, Michino M, Luedtke RR, Javitch JA, Shi L 6 Molecular determinants of selectivity and efficacy at the dopamine D3 receptor Journal of Medicinal Chemistry 55 15 6689–99 August 2012 22632094 3415572 10.1021/jm300482h Legality 2,3-DCPP has been made illegal in Japan and Hungary after having been identified in seized designer drug samples.http://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/dl/meisho.pdf 指定薬物名称・構造式一覧（平成27年9月16日現在） 厚生労働省 16 September 2015 ja 6 January 2015A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása List of derivatives Aripiprazole Cariprazine BAK 2-66 Brilaroxazine (formally RP5063) FAUC-365 [474432-66-1] CJB-090 2xHCl [595584-40-0] NGB 2849 [189061-11-8] NGB 2904 Fb: [189061-11-8] HCl: [189060-98-8] PG-01037 2xHCl: [675599-62-9] PG648 Aripiptranyl (Abilifarnate) Zhang X, Hodgetts K, Rachwal S, Zhao H, Wasley JW, Craven K, Brodbeck R, Kieltyka A, Hoffman D, Bacolod MD, Girard B, Tran J, Thurkauf A 6 trans-1-[(2-Phenylcyclopropyl)methyl]-4-arylpiperazines: mixed dopamine D(2)/D(4) receptor antagonists as potential antipsychotic agents Journal of Medicinal Chemistry 43 21 3923–32 October 2000 11052797 10.1021/jm990562x Michino M, Boateng CA, Donthamsetti P, Yano H, Bakare OM, Bonifazi A, Ellenberger MP, Keck TM, Kumar V, Zhu C, Verma R, Deschamps JR, Javitch JA, Newman AH, Shi L 6 Toward Understanding the Structural Basis of Partial Agonism at the Dopamine D3 Receptor Journal of Medicinal Chemistry 60 2 580–593 January 2017 27983845 10.1021/acs.jmedchem.6b01148 5563258 PGX-2000001 20070142399 So-called R-22 So-called JJC 7−065 R-PG-648July 2025 medicmedic Positional Isomer 180px|thumb|left|class=skin-invert-image|3,4-DCPP, CAS# 57260-67-0 The positional isomer 3,4-dichlorophenylpiperazine (3,4-DCPP) is also known, and acts as both a serotonin releaser via the serotonin transporter, Walline CC, Nichols DE, Carroll FI, Barker EL Comparative molecular field analysis using selectivity fields reveals residues in the third transmembrane helix of the serotonin transporter associated with substrate and antagonist recognition The Journal of Pharmacology and Experimental Therapeutics 325 3 791–800 June 2008 18354055 2637348 10.1124/jpet.108.136200 and a β1-adrenergic receptor blocker, Christopher JA, Brown J, Doré AS, Errey JC, Koglin M, Marshall FH, Myszka DG, Rich RL, Tate CG, Tehan B, Warne T, Congreve M 6 Biophysical fragment screening of the β1-adrenergic receptor: identification of high affinity arylpiperazine leads using structure-based drug design Journal of Medicinal Chemistry 56 9 3446–55 May 2013 23517028 3654563 10.1021/jm400140q though with relatively low affinity at both targets. See also Substituted piperazine Phenylpiperazine ortho-Bromophenylpiperazine References External links Category:Dichlorophenyl compounds Category:1-Phenylpiperazines