para-Methylphenylpiperazine

*para*-Methylphenylpiperazine
Clinical data
Other names	pMPP; 4-Methylphenylpiperazine; 4-MPP; 4-Me-PP; PAL-233; PAL233
Drug class	Serotonin releasing agent
Identifiers
	IUPAC name 1-(4-methylphenyl)piperazine;
CAS Number	39593-08-3;
PubChem CID	83113;
ChemSpider	74982;
ChEMBL	ChEMBL165462;
CompTox Dashboard (EPA)	DTXSID90192706 ;
ECHA InfoCard	100.049.559
Chemical and physical data
Formula	C11H16N2
Molar mass	176.263 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=CC=C(C=C1)N2CCNCC2;
	InChI InChI=1S/C11H16N2/c1-10-2-4-11(5-3-10)13-8-6-12-7-9-13/h2-5,12H,6-9H2,1H3; Key:ONEYFZXGNFNRJH-UHFFFAOYSA-N;

para-Methylphenylpiperazine (pMPP; code name PAL-233), or 4-methylphenylpiperazine (4-MPP or 4-Me-PP), is a designer drug and monoamine releasing agent of the phenylpiperazine family.^[1]^[2]^[3]^[4]^[5] It is a serotonin releasing agent, with an EC₅₀Tooltip half-maximal effective concentration of 220 nM in rat brain synaptosomes, and was inactive in the case of norepinephrine and dopamine (EC₅₀ = >10,000 nM and >20,000 nM, respectively).^[1] It shows very low potency as a dopamine reuptake inhibitor, with an IC₅₀Tooltip half-maximal inhibitory concentration of 9,523 nM, whereas serotonin and norepinephrine were not reported.^[2] Possible activities at serotonin receptors have not been reported.^[1]^[2]

References

^ ^a ^b ^c Severinsen K, Kraft JF, Koldsø H, Vinberg KA, Rothman RB, Partilla JS, et al. (September 2012). "Binding of the amphetamine-like 1-phenyl-piperazine to monoamine transporters". ACS Chemical Neuroscience. 3 (9): 693–705. doi:10.1021/cn300040f. PMC 3447394. PMID 23019496.
^ ^a ^b ^c Reith ME, Blough BE, Hong WC, Jones KT, Schmitt KC, Baumann MH, et al. (February 2015). "Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter". Drug and Alcohol Dependence. 147: 1–19. doi:10.1016/j.drugalcdep.2014.12.005. PMC 4297708. PMID 25548026.
^ "Analytical and Synthetic Studies on Designer Drugs of the Piperazine Class". Office of Justice Programs. 1 July 2014. Retrieved 14 March 2025.
^ Kikura-Hanajiri R, Kawamura M, Uchiyama N, Ogata J, Kamakura H, Saisho K, et al. (June 2008). "[Analytical data of designated substances (Shitei-Yakubutsu) controlled by the Pharmaceutical Affairs Law in Japan, part I: GC-MS and LC-MS]". Yakugaku Zasshi (in Japanese). 128 (6): 971–979. doi:10.1248/yakushi.128.971. PMID 18520144.
^ Uchiyama N, Kawamura M, Kamakura H, Kikura-Hanajiri R, Goda Y (June 2008). "[Analytical data of designated substances (Shitei-Yakubutsu) controlled by the Pharmaceutical Affairs Law in Japan, part II: Color test and TLC]". Yakugaku Zasshi (in Japanese). 128 (6): 981–987. doi:10.1248/yakushi.128.981. PMID 18520145.

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