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]
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Preferred IUPAC name
1-(2,3-Dichlorophenyl)piperazine | |
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3D model (JSmol)
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ChemSpider |
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ECHA InfoCard | 100.126.497 |
PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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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 their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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2,3-DCPP has been made illegal in Japan and Hungary after having been identified in seized designer drug samples.[4][5]
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.
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-Trisubstituted 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.