Jump to content

2,3-Dichlorophenylpiperazine

From Wikipedia, the free encyclopedia
(Redirected fromDichlorophenylpiperazine)
"DCPP" redirects here. For other uses, seeDCPP (disambiguation).
2,3-Dichlorophenylpiperazine
Names
Preferred IUPAC name
1-(2,3-Dichlorophenyl)piperazine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.126.497Edit this at Wikidata
UNII
  • InChI=1S/C10H12Cl2N2/c11-8-2-1-3-9(10(8)12)14-6-4-13-5-7-14/h1-3,13H,4-7H2checkY
    Key: UDQMXYJSNNCRAS-UHFFFAOYSA-NcheckY
  • 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
  • Clc1c(Cl)c(ccc1)N2CCNCC2
Properties
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 theirstandard state(at 25 °C [77 °F], 100 kPa).

2,3-Dichlorophenylpiperazine(2,3-DCPPorDCPP) is achemical compoundfrom thephenylpiperazinefamily. It is both aprecursorin thesynthesisofaripiprazoleand one of itsmetabolites.[1][2]It is unclear whether 2,3-DCPP ispharmacologicallyactive as aserotonin receptoragonist similar to its closeanalogue3-chlorophenylpiperazine(mCPP), though it has been shown to act as apartial agonistof the dopamine D2and D3receptors.[3]

Legality

[edit]

2,3-DCPP has been made illegal in Japan and Hungary after having been identified in seizeddesigner drugsamples.[4][5]

List of derivatives

[edit]
  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-010372xHCl: [675599-62-9]
  10. PG648
  11. Aripiptranyl(Abilifarnate)[6]
  12. [7]
  13. PGX-2000001U.S. patent 20,070,142,399
  14. So-calledR-22[3]
  15. So-calledJJC 7−065[3]
  16. R-PG-648

Positional Isomer

[edit]
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]and a β1-adrenergic receptor blocker,[9]though with relatively low affinity at both targets.

Triple Substituted

[edit]

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.Such 3,4,5-Trisubstituted aromatic entities is already known from clenbuterol. Leading toCID:151687078WO 1993021179(Ex 6is a concrete example of this) i.e. 1-(4-Amino-3,5-dichlorophenyl)-4-(4-phthalimido-1- butyl)piperazine.

See also

[edit]

References

[edit]
  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.PMID20369792.
  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.PMID17691920.
  3. ^abcNewman 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.PMC3415572.PMID22632094.
  4. ^"Chỉ định dược vật danh xưng ・ cấu tạo thức nhất lãm ( bình thành 27 niên 9 nguyệt 16 nhật hiện tại )"(PDF)(in Japanese). Hậu sinh 労 động tỉnh. 16 September 2015.Retrieved6 January2015.
  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.PMID11052797.
  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 D3Receptor ".Journal of Medicinal Chemistry.60(2): 580–593.doi:10.1021/acs.jmedchem.6b01148.PMC5563258.PMID27983845.
  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.PMC2637348.PMID18354055.
  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.PMC3654563.PMID23517028.
[edit]
Retrieved from "https://en.wikipedia.org/w/index.php?title=2,3-Dichlorophenylpiperazine&oldid=1198706354"