| Revision as of 16:58, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 443262944 of page 2,3-Dichlorophenylpiperazine for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 10:34, 22 November 2024 edit Pi bot (talk | contribs)Bots, IP block exemptions68,307 editsm Changing locally defined but nonexistent Commons category (Category:2,3-Dichlorophenylpiperazines) to the one from Wikidata (Category:2,3-Dichlorophenylpiperazine) |
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{{Redirect|DCPP}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| verifiedrevid = 443261654 |
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| verifiedrevid = 477210276 |
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| ImageFile = Dichlorophenylpiperazine-ifa.png |
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| ImageFile = Dichlorophenylpiperazine-ifa.png |
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| ImageSize = |
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| ImageSize = |
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| IUPACName = 1-(2,3-dichlorophenyl)piperazine |
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| PIN = 1-(2,3-Dichlorophenyl)piperazine |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| InChI1 = 1/C10H12Cl2N2/c11-8-2-1-3-9(10(8)12)14-6-4-13-5-7-14/h1-3,13H,4-7H2 |
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| InChI1 = 1/C10H12Cl2N2/c11-8-2-1-3-9(10(8)12)14-6-4-13-5-7-14/h1-3,13H,4-7H2 |
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| InChIKey = UDQMXYJSNNCRAS-UHFFFAOYAH |
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| InChIKey = UDQMXYJSNNCRAS-UHFFFAOYAH |
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| InChIKey1 = UDQMXYJSNNCRAS-UHFFFAOYAH |
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| InChIKey1 = UDQMXYJSNNCRAS-UHFFFAOYAH |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 41202-77-1 --> |
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| PubChem = 851833 |
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| CASNo = 41202-77-1 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 891W3EV0B1 |
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| PubChem = 851833 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C10H12Cl2N2/c11-8-2-1-3-9(10(8)12)14-6-4-13-5-7-14/h1-3,13H,4-7H2 |
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| StdInChI = 1S/C10H12Cl2N2/c11-8-2-1-3-9(10(8)12)14-6-4-13-5-7-14/h1-3,13H,4-7H2 |
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| StdInChIKey = UDQMXYJSNNCRAS-UHFFFAOYSA-N |
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| StdInChIKey = UDQMXYJSNNCRAS-UHFFFAOYSA-N |
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| ChemSpiderID = 744460 |
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| ChemSpiderID = 744460 |
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| SMILES = Clc1c(Cl)c(ccc1)N2CCNCC2 |
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| SMILES = Clc1c(Cl)c(ccc1)N2CCNCC2 |
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| InChI =1S/C10H12Cl2N2/c11-8-2-1-3-9(10(8)12)14-6-4-13-5-7-14/h1-3,13H,4-7H2 |
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| InChI =1S/C10H12Cl2N2/c11-8-2-1-3-9(10(8)12)14-6-4-13-5-7-14/h1-3,13H,4-7H2 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>10</sub>H<sub>12</sub>Cl<sub>2</sub>N<sub>2</sub> |
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| Formula = C<sub>10</sub>H<sub>12</sub>Cl<sub>2</sub>N<sub>2</sub> |
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| MolarMass = 231.12 g/mol |
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| MolarMass = 231.12 g/mol |
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| Appearance = brown oil |
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| Appearance = brown oil |
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| Density = 1.272g/cm<sup>3</sup> °C |
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| Density = 1.272g/cm<sup>3</sup> °C |
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| MeltingPt = 242-244°C |
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| MeltingPtC = 242 to 244 |
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| BoilingPt = 365.1°C @ 760mmHg |
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| BoilingPtC = 365.1 |
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| BoilingPt_notes = at 760mmHg |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = 174.6°C |
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| FlashPtC = 174.6 |
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'''2,3-Dichlorophenylpiperazine''' ('''2,3-DCPP''' or '''DCPP''') is a ] from the ] family. It is both a ] in the ] of ] and one of its ]s.<ref name="pmid20369792">{{cite journal | vauthors = Leś A, Badowska-Rosłonek K, Łaszcz M, Kamieńska-Duda A, Baran P, Kaczmarek Ł | title = Optimization of aripiprazole synthesis | journal = Acta Poloniae Pharmaceutica | volume = 67 | issue = 2 | pages = 151–7 | year = 2010 | pmid = 20369792 }}</ref><ref name="pmid17691920">{{cite journal | vauthors = Caccia S | title = N-dealkylation of arylpiperazine derivatives: disposition and metabolism of the 1-aryl-piperazines formed | journal = Current Drug Metabolism | volume = 8 | issue = 6 | pages = 612–22 | date = August 2007 | pmid = 17691920 | doi = 10.2174/138920007781368908 }}</ref> It is unclear whether 2,3-DCPP is ] active as a ] agonist similar to its close ] ] (''m''CPP), though it has been shown to act as a ] of the dopamine D<sub>2</sub> and D<sub>3</sub> receptors.<ref name="pmid22632094">{{cite journal | vauthors = Newman AH, Beuming T, Banala AK, Donthamsetti P, Pongetti K, LaBounty A, Levy B, Cao J, Michino M, Luedtke RR, Javitch JA, Shi L | display-authors = 6 | title = Molecular determinants of selectivity and efficacy at the dopamine D3 receptor | journal = Journal of Medicinal Chemistry | volume = 55 | issue = 15 | pages = 6689–99 | date = August 2012 | pmid = 22632094 | pmc = 3415572 | doi = 10.1021/jm300482h }}</ref> |
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==Legality== |
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2,3-DCPP has been made illegal in Japan and Hungary after having been identified in seized ] samples.<ref>{{cite web | url=http://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/dl/meisho.pdf | title=指定薬物名称・構造式一覧（平成27年9月16日現在） | publisher=厚生労働省 | date=16 September 2015 | language=ja | access-date=6 January 2015}}</ref><ref></ref> |
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==List of derivatives== |
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#] |
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#] |
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#BAK 2-66 |
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#] (formally RP5063) |
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#FAUC-365 |
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#CJB-090 2xHCl |
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#NGB 2849 |
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#NGB 2904 Fb: HCl: |
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# 2xHCl: |
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#PG648 |
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# (Abilifarnate)<ref name="ZhangHodgetts2000">{{cite journal | vauthors = 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 | display-authors = 6 | title = trans-1--4-arylpiperazines: mixed dopamine D(2)/D(4) receptor antagonists as potential antipsychotic agents | journal = Journal of Medicinal Chemistry | volume = 43 | issue = 21 | pages = 3923–32 | date = October 2000 | pmid = 11052797 | doi = 10.1021/jm990562x }}</ref> |
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#<ref name="MichinoBoateng2017">{{cite journal | vauthors = 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 | display-authors = 6 | title = Toward Understanding the Structural Basis of Partial Agonism at the Dopamine D<sub>3</sub> Receptor | journal = Journal of Medicinal Chemistry | volume = 60 | issue = 2 | pages = 580–593 | date = January 2017 | pmid = 27983845 | doi = 10.1021/acs.jmedchem.6b01148 | pmc = 5563258 }}</ref> |
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# {{US patent|20070142399}} |
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#So-called <ref name="pmid22632094"/> |
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#So-called <ref name="pmid22632094"/> |
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==Positional Isomer== |
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The positional isomer 3,4-dichlorophenylpiperazine (3,4-DCPP) is also known, and acts as both a serotonin releaser via the ],<ref name="pmid18354055">{{cite journal | vauthors = Walline CC, Nichols DE, Carroll FI, Barker EL | title = Comparative molecular field analysis using selectivity fields reveals residues in the third transmembrane helix of the serotonin transporter associated with substrate and antagonist recognition | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 325 | issue = 3 | pages = 791–800 | date = June 2008 | pmid = 18354055 | pmc = 2637348 | doi = 10.1124/jpet.108.136200 }}</ref> and a β<sub>1</sub>-adrenergic receptor blocker,<ref name="pmid23517028">{{cite journal | vauthors = Christopher JA, Brown J, Doré AS, Errey JC, Koglin M, Marshall FH, Myszka DG, Rich RL, Tate CG, Tehan B, Warne T, Congreve M | display-authors = 6 | title = Biophysical fragment screening of the β1-adrenergic receptor: identification of high affinity arylpiperazine leads using structure-based drug design | journal = Journal of Medicinal Chemistry | volume = 56 | issue = 9 | pages = 3446–55 | date = May 2013 | pmid = 23517028 | pmc = 3654563 | doi = 10.1021/jm400140q }}</ref> though with relatively low affinity at both targets. |
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==Triple Substituted== |
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The 3,4,5-Trichlorophenylpiperazine ("3 stripes") is also a highly regarded arrangement & has been awarded the Beecham patent of {{US patent|4139621}}. Such 3,4,5-Trisubstituted aromatic entities is already known from clenbuterol. Leading to {{Cite patent|country=WO|number=1993021179}} ('''Ex 6''' is a concrete example of this) i.e. 1-(4-Amino-3,5-dichlorophenyl)-4-(4-phthalimido-1- butyl)piperazine. |
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== See also == |
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* ] |
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* ] |
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== References == |
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{{Reflist}} |
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== External links == |
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*{{Commonscatinline|2,3-Dichlorophenylpiperazine}} |
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{{Piperazines}} |
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{{DEFAULTSORT:Dichlorophenylpiperazine, 2,3-}} |
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