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
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.049.511 Edit 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 as oMPP, oMePP, 1-(2-methylphenyl)piperazine, 2-MPP, and 2-MePP) is a psychoactive designer drug of the phenylpiperazine group.[1][2] It acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA), with EC50 values for induction of monoamine release of 175 nM for serotonin, 39.1 nM for norepinephrine, and 296–542 nM for dopamine.[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]

The 2,3-methyl and 4-methyl analogues show diminished activity as dopamine 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

References

  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. doi:10.1007/s00204-013-1057-x. PMID 23685794. S2CID 253718416.
  3. ^ a b c Kohut 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. ^ a b c d Reith 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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