Phenylpiperazine
Chemical compound
From Wikipedia, the free encyclopedia
1-Phenylpiperazine (1-PP or PP) is a simple chemical compound and drug featuring a phenyl group bound to a piperazine ring.[1] The suffix â-piprazoleâ is sometimes used in the names of drugs to indicate they belong to this class.[2]
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| Names | |
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| Preferred IUPAC name
1-Phenylpiperazine | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.001.969 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C10H14N2 | |
| Molar mass | 162.23 g/mol |
| Appearance | clear colourless to yellow liquid |
| Density | 1.028g/cm3 |
| Melting point | 18.8 °C (65.8 °F; 291.9 K) |
| Boiling point | 287.2 °C (549.0 °F; 560.3 K) at 760mmHg |
| insoluble | |
| Hazards | |
| Flash point | 138.3 °C (280.9 °F; 411.4 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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It is a rigid analogue of amphetamine.[1][3][4] Similarly to amphetamine, 1-PP is a monoamine releasing agent, with EC50 values for monoamine release of 186 nM for norepinephrine, 880 nM for serotonin, and 2,530 nM for dopamine.[1] Based on the preceding values, it is about 4.7-fold less potent in releasing serotonin than norepinephrine and about 13.6-fold less potent in releasing dopamine than norepinephrine.[1] Hence, 1-PP is a modestly selective norepinephrine releasing agent (NRA), or could alternatively be thought of as an imbalanced serotoninânorepinephrine releasing agent (SNRA) or serotoninânorepinephrineâdopamine releasing agent (SNDRA).[1]
Other homologues and rigid analogues of amphetamine besides 1-PP include 2-aminotetralin (2-AT), 2-amino-1,2-dihydronaphthalene (2-ADN), 2-aminoindane (2-AI), 1-naphthylaminopropane (1-NAP), 2-naphthylaminopropane (2-NAP), 6-AB, and 7-AB.[3][4][5]
1-Phenylpiperazine shows toxicity at sufficiently high doses; its oral LD50 in rats is 210 mg/kg.[6]
Numerous derivatives of 1-PP, or substituted phenylpiperazines, exist.[7][1] Some examples include meta-chlorophenylpiperazine (mCPP), 3-trifluoromethylphenylpiperazine (TFMPP), and para-methoxyphenylpiperazine (pMeOPP).[7][1][8]
