Ortho-Methylphenylpiperazine

*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 ;
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;

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]

^ 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.
^ 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.
^ ^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.
^ ^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.

[pmid11516887-1] 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.

[pmid23685794-2] 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.

[pmid28889212-3] 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.

[pmid25548026-4] 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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