2,3-Dichlorophenylpiperazine

"DCPP" redirects here. For other uses, see DCPP (disambiguation).

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	41202-77-1 Y
3D model (JSmol)	Interactive image
ChemSpider	744460 Y
ECHA InfoCard	100.126.497
PubChem CID	851833
UNII	891W3EV0B1 Y
CompTox Dashboard (EPA)	DTXSID90961499
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 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)^[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^{[dead link]}

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,^[8] and a β₁-adrenergic receptor blocker,^[9] 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 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.

See also

• Substituted piperazine
• Phenylpiperazine
• ortho-Bromophenylpiperazine