2,3-Dichlorophenylpiperazine Names Preferred IUPAC name 1-(2,3-Dichlorophenyl)piperazine
Identifiers ChemSpider ECHA InfoCard 100.126.497 UNII InChI=1S/C10H12Cl2N2/c11-8-2-1-3-9(10(8)12)14-6-4-13-5-7-14/h1-3,13H,4-7H2
Y Key: UDQMXYJSNNCRAS-UHFFFAOYSA-N
Y InChI=1S/C10H12Cl2N2/c11-8-2-1-3-9(10(8)12)14-6-4-13-5-7-14/h1-3,13H,4-7H2
Key: UDQMXYJSNNCRAS-UHFFFAOYAH
InChI=1/C10H12Cl2N2/c11-8-2-1-3-9(10(8)12)14-6-4-13-5-7-14/h1-3,13H,4-7H2
Key: UDQMXYJSNNCRAS-UHFFFAOYAH
Properties C10 H12 Cl2 N2 Molar mass 231.12 g/mol Appearance brown oil Density 1.272g/cm3 °C Melting point 242 to 244 °C (468 to 471 °F; 515 to 517 K) Boiling point 365.1 °C (689.2 °F; 638.2 K) at 760mmHg Hazards Flash point 174.6 °C (346.3 °F; 447.8 K) Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
2,3-Dichlorophenylpiperazine (2,3-DCPP orDCPP ) is achemical compound from thephenylpiperazine family. It is both aprecursor in thesynthesis ofaripiprazole and one of itsmetabolites .[ 1] [ 2] pharmacologically active as aserotonin receptor agonist similar to its closeanalogue 3-chlorophenylpiperazine (m CPP), though it has been shown to act as apartial agonist of thedopamine D2 andD3 receptors.[ 3]
2,3-DCPP has been made illegal in Japan and Hungary after having been identified in seizeddesigner drug samples.[ 4] [ 5]
List of derivatives [ edit ] 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)[ 6] [ 7] PGX-2000001 U.S. patent 20,070,142,399 So-calledR-22 [ 3] So-calledJJC 7−065 [ 3] R-PG-648 [dead link 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 theserotonin transporter ,[ 8] 1 -adrenergic receptor blocker,[ 9]
The 3,4,5-Trichlorophenylpiperazine [67305-64-0] ("3 stripes") is also a highly regarded arrangement & has been awarded the Beecham patent ofU.S. patent 4,139,621 CID:151687078 WO 1993021179 Ex 6 is a concrete example of this) i.e. 1-(4-Amino-3,5-dichlorophenyl)-4-(4-phthalimido-1- butyl)piperazine.
^ Leś A, Badowska-Rosłonek K, Łaszcz M, Kamieńska-Duda A, Baran P, Kaczmarek Ł (2010). "Optimization of aripiprazole synthesis".Acta Poloniae Pharmaceutica .67 (2):151– 7.PMID 20369792 . ^ Caccia S (August 2007). "N-dealkylation of arylpiperazine derivatives: disposition and metabolism of the 1-aryl-piperazines formed".Current Drug Metabolism .8 (6):612– 22.doi :10.2174/138920007781368908 .PMID 17691920 . ^a b c Newman AH, Beuming T, Banala AK, Donthamsetti P, Pongetti K, LaBounty A, et al. (August 2012)."Molecular determinants of selectivity and efficacy at the dopamine D3 receptor" .Journal of Medicinal Chemistry .55 (15):6689– 99.doi :10.1021/jm300482h .PMC 3415572 PMID 22632094 . ^ "指定薬物名称・構造式一覧（平成27年9月16日現在）" (PDF) (in Japanese). 厚生労働省. 16 September 2015. Retrieved6 January 2015 .^ A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása ^ Zhang X, Hodgetts K, Rachwal S, Zhao H, Wasley JW, Craven K, et al. (October 2000). "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.doi :10.1021/jm990562x .PMID 11052797 . ^ Michino M, Boateng CA, Donthamsetti P, Yano H, Bakare OM, Bonifazi A, et al. (January 2017)."Toward Understanding the Structural Basis of Partial Agonism at the Dopamine D3 Receptor" .Journal of Medicinal Chemistry .60 (2):580– 593.doi :10.1021/acs.jmedchem.6b01148 .PMC 5563258 PMID 27983845 . ^ Walline CC, Nichols DE, Carroll FI, Barker EL (June 2008)."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.doi :10.1124/jpet.108.136200 .PMC 2637348 PMID 18354055 . ^ Christopher JA, Brown J, Doré AS, Errey JC, Koglin M, Marshall FH, et al. (May 2013)."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.doi :10.1021/jm400140q .PMC 3654563 PMID 23517028 .
Phenylpiperazines 1-Phenylpiperazine (1-PP; PP) 3,4-CFP 2C-B-PP Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-7625 EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Fluanisone Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635 Benzylpiperazines Naphthylpiperazines Quinolinylpiperazines Diphenylalkylpiperazines Pyrimidinylpiperazines Pyridinylpiperazines Benzo(iso)thiazolyl piperazines Tricyclic -linked piperazinesOthers/uncategorized
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