Phenylpiperazine

_Hello all readers, today we are going to talk about Phenylpiperazine. This is a very broad and relevant topic today, covering a wide variety of aspects ranging from _aspect1 to _aspect2. Phenylpiperazine is a very influential figure in the _tema1 field and his legacy has left its mark on _tema2. Throughout history, Phenylpiperazine has been the object of controversy and admiration, generating debates and reflections that have transcended time. Therefore, it is important to delve into its origins, impact and meaning, to better understand its importance in _tema3 and _tema4. In this article we will explore the different nuances of Phenylpiperazine and how it has marked a before and after in _tema5. Stay tuned for the following lines to discover more about this exciting topic._

Not to be confused with Substituted phenylpiperazine.
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 , 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

References

  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.