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ortho-Methylphenylpiperazine

From Wikipedia, the free encyclopedia
Chemical compound

Not to be confused withortho-Methoxyphenylpiperazine.
Pharmaceutical compound
ortho-Methylphenylpiperazine
Clinical data
Other namesoMPP; oMePP; 2-Methylphenylpiperazine; 2-MPP; 2-MePP; 1-(o-Tolyl)piperazine; PAL-169
Identifiers
  • 1-(2-Methylphenyl)piperazine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.049.511Edit this at Wikidata
Chemical and physical data
FormulaC11H16N2
Molar mass176.263 g·mol−1
3D model (JSmol)
  • CC1=CC=CC=C1N2CCNCC2
  • InChI=1S/C11H16N2/c1-10-4-2-3-5-11(10)13-8-6-12-7-9-13/h2-5,12H,6-9H2,1H3
  • Key:WICKLEOONJPMEQ-UHFFFAOYSA-N

ortho-Methylphenylpiperazine (also known asoMPP,oMePP,1-(2-methylphenyl)piperazine,2-MPP, and2-MePP) is apsychoactivedesigner drug of thephenylpiperazine group.[1][2] It acts as aserotonin–norepinephrine–dopamine releasing agent (SNDRA), withEC50 values for induction ofmonoaminerelease of 175 nM forserotonin, 39.1 nM fornorepinephrine, and 296–542 nM fordopamine.[3][4] As such, it has about 4.5-fold preference for induction of norepinephrine release over serotonin, and about 7.6- to 13.9-fold preference for induction of norepinephrine release over dopamine.[3][4]

The2,3-methyl and4-methylanalogues show diminished activity asdopamine releasing agents with respective EC50 values of 1,207 nM and 9,523 nM.[3][4] However, at the same time, induction of serotonin and norepinephrine release is retained and more balanced in the 2,3-methyl analogue, with respective EC50 values of 26 nM and 56 nM.[4]

See also

[edit]

References

[edit]
  1. ^de Boer D, Bosman IJ, Hidvégi E, Manzoni C, Benkö AA, dos Reys LJ, Maes RA (2001). "Piperazine-like compounds: a new group of designer drugs-of-abuse on the European market".Forensic Sci. Int.121 (1–2):47–56.doi:10.1016/s0379-0738(01)00452-2.PMID 11516887.
  2. ^Monteiro MS, Bastos Mde L, Guedes de Pinho P, Carvalho M (2013). "Update on 1-benzylpiperazine (BZP) party pills".Arch. Toxicol.87 (6):929–47.Bibcode:2013ArTox..87..929M.doi:10.1007/s00204-013-1057-x.PMID 23685794.S2CID 253718416.
  3. ^abcKohut SJ, Jacobs DS, Rothman RB, Partilla JS, Bergman J, Blough BE (2017)."Cocaine-like discriminative stimulus effects of "norepinephrine-preferring" monoamine releasers: time course and interaction studies in rhesus monkeys".Psychopharmacology.234 (23–24):3455–3465.doi:10.1007/s00213-017-4731-5.PMC 5747253.PMID 28889212.
  4. ^abcdReith ME, Blough BE, Hong WC, Jones KT, Schmitt KC, Baumann MH, Partilla JS, Rothman RB, Katz JL (2015)."Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter".Drug Alcohol Depend.147:1–19.doi:10.1016/j.drugalcdep.2014.12.005.PMC 4297708.PMID 25548026.
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DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
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