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Phenylpiperazine

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Phenylpiperazine
Skeletal formula of phenylpiperazine
Ball-and-stick model of the phenylpiperazine molecule
Names
Preferred IUPAC name
1-Phenylpiperazine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.969 Edit this at Wikidata
UNII
  • InChI=1S/C10H14N2/c1-2-4-10(5-3-1)12-8-6-11-7-9-12/h1-5,11H,6-9H2 checkY
    Key: YZTJYBJCZXZGCT-UHFFFAOYSA-N checkY
  • c1cc(ccc1)N2CCNCC2
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).

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 ‘-piprazole’ is sometimes used in the names of drugs to indicate they belong to this class.[2]

It is a rigid analogue of amphetamine.[1][3][4] Similarly to amphetamine, 1-PP is a monoamine releasing agent, with EC50Tooltip half-maximal effective concentration 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 serotonin–norepinephrine releasing agent (SNRA) or serotonin–norepinephrine–dopamine 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-ABTooltip 6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene, and 7-ABTooltip 7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene.[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]

See also

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References

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  1. ^ a b c d e f g Severinsen K, Kraft JF, Koldsø H, Vinberg KA, Rothman RB, Partilla JS, Wiborg O, Blough B, Schiøtt B, Sinning S (September 2012). "Binding of the amphetamine-like 1-phenyl-piperazine to monoamine transporters". ACS Chem Neurosci. 3 (9): 693–705. doi:10.1021/cn300040f. PMC 3447394. PMID 23019496.
  2. ^ World Health Organization (WHO) (2006). "The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances" (PDF). Archived from the original (PDF) on 2008-12-14. Retrieved 27 April 2010.
  3. ^ a b Oberlender R, Nichols DE (March 1991). "Structural variation and (+)-amphetamine-like discriminative stimulus properties". Pharmacology, Biochemistry, and Behavior. 38 (3): 581–586. doi:10.1016/0091-3057(91)90017-V. PMID 2068194. S2CID 19069907.
  4. ^ a b Glennon RA, Young R, Hauck AE, McKenney JD (December 1984). "Structure-activity studies on amphetamine analogs using drug discrimination methodology". Pharmacol Biochem Behav. 21 (6): 895–901. doi:10.1016/s0091-3057(84)80071-4. PMID 6522418.
  5. ^ Hathaway BA, Nichols DE, Nichols MB, Yim GK (May 1982). "A new, potent, conformationally restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene". Journal of Medicinal Chemistry. 25 (5): 535–538. doi:10.1021/jm00347a011. PMID 6123601.
  6. ^ "1-Phenylpiperazine". pubchem.ncbi.nlm.nih.gov.
  7. ^ a b Elliott S (2011). "Current awareness of piperazines: pharmacology and toxicology". Drug Test Anal. 3 (7–8): 430–438. doi:10.1002/dta.307. PMID 21744514.
  8. ^ Baumann MH, Clark RD, Budzynski AG, Partilla JS, Blough BE, Rothman RB (October 2004). "Effects of "Legal X" piperazine analogs on dopamine and serotonin release in rat brain". Ann N Y Acad Sci. 1025: 189–197. doi:10.1196/annals.1316.024. PMID 15542717.
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