Ortho-Methylphenylpiperazine

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]

Not to be confused with ortho-Methoxyphenylpiperazine.

ortho-Methylphenylpiperazine

Clinical data
Other names	oMPP; oMePP; 2-Methylphenylpiperazine; 2-MPP; 2-MePP; 1-(o-Tolyl)piperazine; PAL-169
Identifiers
IUPAC name 1-(2-Methylphenyl)piperazine
CAS Number	39512-51-1 Y
PubChem CID	91965
ChemSpider	83039
UNII	6P26KQQ7V5
ChEMBL	ChEMBL9746
CompTox Dashboard (EPA)	DTXSID00192651
ECHA InfoCard	100.049.511
Chemical and physical data
Formula	C11H16N2
Molar mass	176.263 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC=CC=C1N2CCNCC2
InChI 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

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

• Substituted piperazine
• ortho-Bromophenylpiperazine