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general/2-3-dichlorophenylpiperazines

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2,3-Dichlorophenylpiperazine

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. 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.

Legality

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

List of derivatives

  1. Aripiprazole
  2. Cariprazine
  3. BAK 2-66
  4. Brilaroxazine (formally RP5063)
  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)
  12. PGX-2000001
  13. So-called R-22
  14. So-called JJC 7−065
  15. R-PG-648

Positional Isomer

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, and a β1-adrenergic receptor blocker, though with relatively low affinity at both targets.

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 . Such 3,4,5-Trisubstituted aromatic entities is already known from clenbuterol. Leading to CID:151687078 (Ex 6 is a concrete example of this) i.e. 1-(4-Amino-3,5-dichlorophenyl)-4-(4-phthalimido-1- butyl)piperazine.

References

References

  1. (2010). "Optimization of aripiprazole synthesis". Acta Poloniae Pharmaceutica.
  2. (August 2007). "N-dealkylation of arylpiperazine derivatives: disposition and metabolism of the 1-aryl-piperazines formed". Current Drug Metabolism.
  3. (August 2012). "Molecular determinants of selectivity and efficacy at the dopamine D3 receptor". Journal of Medicinal Chemistry.
  4. (16 September 2015). "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.
  5. [http://www.daath.hu/incoming/designer_jogi_lista_20150903_BSZKI_Daath_kieg.pdf A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása]
  6. (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.
  7. (January 2017). "Toward Understanding the Structural Basis of Partial Agonism at the Dopamine D3 Receptor". Journal of Medicinal Chemistry.
  8. (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.
  9. (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.
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