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| Names | |
|---|---|
| Preferred IUPAC name 1-Phenylpiperazine | |
| Identifiers | |
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3D model (JSmol) | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.001.969 |
| UNII | |
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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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
1-Phenylpiperazine (1-PP orPP) is a simplechemical compound anddrug featuring aphenylgroup bound to apiperazinering.[1] The suffix ‘-piprazole’ is sometimes used in the names ofdrugs to indicate they belong to this class.[2]
It is a rigidanalogue ofamphetamine.[1][3][4] Similarly to amphetamine, 1-PP is amonoamine releasing agent, withEC50Tooltip half-maximal effective concentration values formonoamine release of 186 nM fornorepinephrine, 880 nM forserotonin, and 2,530 nM fordopamine.[1] Based on the preceding values, it is about 4.7-fold lesspotent in releasing serotonin than norepinephrine and about 13.6-fold less potent in releasing dopamine than norepinephrine.[1] Hence, 1-PP is a modestlyselectivenorepinephrine releasing agent (NRA), or could alternatively be thought of as an imbalancedserotonin–norepinephrine releasing agent (SNRA) orserotonin–norepinephrine–dopamine releasing agent (SNDRA).[1]
Other homologues and rigid analogues of amphetamine besides 1-PP include2-aminotetralin (2-AT),2-amino-1,2-dihydronaphthalene (2-ADN),2-aminoindane (2-AI),1-naphthylaminopropane (1-NAP),2-naphthylaminopropane (2-NAP),6-ABTooltip 6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene, and7-ABTooltip 7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene.[3][4][5]
1-Phenylpiperazine showstoxicity at sufficiently high doses; itsoralLD50 in rats is 210 mg/kg.[6]
Numerousderivatives of 1-PP, orsubstituted phenylpiperazines, exist.[7][1] Some examples includemeta-chlorophenylpiperazine (mCPP),3-trifluoromethylphenylpiperazine (TFMPP), andpara-methoxyphenylpiperazine (pMeOPP).[7][1][8]
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