Chemistry:Ortho-Methylphenylpiperazine

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Short description: Chemical compound


ortho-Methylphenylpiperazine
2-Methylphenylpiperazine.svg
Clinical data
Other namesoMPP; oMePP; 2-Methylphenylpiperazine; 2-MPP; 2-MePP; 1-(o-Tolyl)piperazine; PAL-169
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC11H16N2
Molar mass176.263 g·mol−1
3D model (JSmol)

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. "Piperazine-like compounds: a new group of designer drugs-of-abuse on the European market". Forensic Sci. Int. 121 (1–2): 47–56. 2001. doi:10.1016/s0379-0738(01)00452-2. PMID 11516887. 
  2. "Update on 1-benzylpiperazine (BZP) party pills". Arch. Toxicol. 87 (6): 929–47. 2013. doi:10.1007/s00204-013-1057-x. PMID 23685794. 
  3. 3.0 3.1 3.2 "Cocaine-like discriminative stimulus effects of "norepinephrine-preferring" monoamine releasers: time course and interaction studies in rhesus monkeys". Psychopharmacology 234 (23–24): 3455–3465. 2017. doi:10.1007/s00213-017-4731-5. PMID 28889212. 
  4. 4.0 4.1 4.2 4.3 "Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter". Drug Alcohol Depend 147: 1–19. 2015. doi:10.1016/j.drugalcdep.2014.12.005. PMID 25548026.