2,3-Dichlorophenylpiperazine

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.[1][2] 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.[3]

2,3-Dichlorophenylpiperazine
Names
Preferred IUPAC name
1-(2,3-Dichlorophenyl)piperazine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.126.497
PubChem CID
UNII
InChI
  • 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
SMILES
  • Clc1c(Cl)c(ccc1)N2CCNCC2
Properties
Chemical formula
 C10H12Cl2N2
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).
N verify (what is YN ?)
Infobox references

Legality

2,3-DCPP has been made illegal in Japan and Hungary after having been identified in seized designer drug samples.[4][5]

List of derivatives
  1. Aripiprazole
  2. Cariprazine
  3. BAK 2-66
  4. Brilaroxazine (formally RP-5063)
  5. FAUC-365 [474432-66-1]
  6. CJB-090 2xHCl [595584-40-0]
  7. NGB 2849 [189061-11-8]
  8. NGB 2904 Fb: [189061-11-8] HCl: [189060-98-8]
  9. PG-01037 2xHCl: [675599-62-9]
  10. PG648
  11. Aripiptranyl (Abilifarnate)[6]
  12. [7]
  13. PGX-2000001 U.S. Patent 20,070,142,399
  14. So-called R-22[3]
  15. So-called JJC 7−065[3]
  16. R-PG-648

Positional Isomer

The positional isomer 3,4-dichlorophenylpiperazine (3,4-DCPP) is also known, and acts as both a serotonin releaser via the serotonin transporter,[8] and a β1-adrenergic receptor blocker,[9] though with relatively low affinity at both targets.

3,4-DCPP, CAS# 57260-67-0

Triple Substituted

The 3,4,5-Trichlorophenylpiperazine [67305-64-0] ("3 stripes") is also a highly regarded arrangement & has been awarded the Beecham patent of U.S. Patent 4,139,621. Such 3,4,5-Trisunstituted aromatic entities is already known from clenbuterol. Leading to 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.

See also

References
  1. 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.
  2. 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.
  3. 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.
  4. "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. Retrieved 6 January 2015.
  5. A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása
  6. 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.
  7. 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.
  8. 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.
  9. 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.
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