4'-Methyl-α-pyrrolidinopropiophenone

For other uses, see MPPP (disambiguation).

Not to be confused with desmethylprodine (opioid drug with acronym MPPP), MPTP (neurotoxic impurity of desmethylprodine synthesis) or MPP⁺ (neurotoxic metabolite of MPTP).

4'-Methyl-α-pyrrolidinopropiophenone (4-MePPP, MPPP or MαPPP) is a stimulant drug and substituted cathinone. It is structurally very similar to α-PPP, with only one added methyl group in the para position on the phenyl ring. 4-MePPP was sold in Germany as a designer drug in the late 1990s and early 2000s,^[2][3][4] along with a number of other pyrrolidinophenone derivatives.^[5][6] Although it has never achieved the same international popularity as its better-known relations α-PPP and MDPV, 4-MePPP is still sometimes found as an ingredient of grey-market "bath salt" blends^[7] such as "NRG-3".^[7]

4'-Methyl-α-pyrrolidinopropiophenone

Legal status
Legal status	DE: Anlage I (Authorized scientific use only) UK: Class B US: Schedule I Banned in Sweden [1]
Identifiers
IUPAC name (RS)-1-(4-methylphenyl)-2-(1-pyrrolidinyl)-1-propanone
CAS Number	28117-80-8 1313393-58-6 (hydrochloride)
PubChem CID	6430745
ChemSpider	4936084
UNII	0TY023967I
CompTox Dashboard (EPA)	DTXSID80891438
Chemical and physical data
Formula	C14H19NO
Molar mass	217.312 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC=C(C=C1)C(=O)C(C)N2CCCC2
InChI InChI=1S/C14H19NO/c1-11-5-7-13(8-6-11)14(16)12(2)15-9-3-4-10-15/h5-8,12H,3-4,9-10H2,1-2H3 Key:APSJUNFBAXIXLK-UHFFFAOYSA-N

Legality

In the United States 4-MePPP is considered a schedule 1 controlled substance as an positional isomer of alpha-pyrrolidinopentiophenone (α-PVP)^[8]

See also

• α-Pyrrolidinopropiophenone (α-PPP)
• 4'-Methoxy-α-pyrrolidinopropiophenone (MOPPP)
• 3,4-Methylenedioxy-α-pyrrolidinopropiophenone (MDPPP)
• 3',4'-Methylenedioxy-α-pyrrolidinobutiophenone (MDPBP)

References

1. "Cannabinoider föreslås bli klassade som hälsofarlig vara" [Cannabinoids are proposed to be classified as a health hazard]. Folkhälsomyndigheten [The Public Health Authority] (in Swedish). Retrieved 29 June 2015.
2. Springer D, Peters FT, Fritschi G, Maurer HH (June 2002). "Studies on the metabolism and toxicological detection of the new designer drug 4'-methyl-alpha-pyrrolidinopropiophenone in urine using gas chromatography-mass spectrometry". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 773 (1): 25–33. doi:10.1016/S1570-0232(01)00578-5. PMID 12015267.
3. Springer D, Paul LD, Staack RF, Kraemer T, Maurer HH (August 2003). "Identification of cytochrome p450 enzymes involved in the metabolism of 4'-methyl-alpha-pyrrolidinopropiophenone, a novel scheduled designer drug, in human liver microsomes". Drug Metabolism and Disposition. 31 (8): 979–982. doi:10.1124/dmd.31.8.979. PMID 12867484.
4. Springer D, Fritschi G, Maurer HH (November 2003). "Metabolism of the new designer drug alpha-pyrrolidinopropiophenone (PPP) and the toxicological detection of PPP and 4'-methyl-alpha-pyrrolidinopropiophenone (MPPP) studied in rat urine using gas chromatography-mass spectrometry". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 796 (2): 253–266. doi:10.1016/j.jchromb.2003.07.008. PMID 14581066.
5. Maurer HH, Kraemer T, Springer D, Staack RF (April 2004). "Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (ecstasy), piperazine, and pyrrolidinophenone types: a synopsis". Therapeutic Drug Monitoring. 26 (2): 127–131. doi:10.1097/00007691-200404000-00007. PMID 15228152. S2CID 9255084.
6. Staack RF, Maurer HH (June 2005). "Metabolism of designer drugs of abuse". Current Drug Metabolism. 6 (3): 259–274. doi:10.2174/1389200054021825. PMID 15975043.
7. Brandt SD, Freeman S, Sumnall HR, Measham F, Cole J (September 2011). "Analysis of NRG 'legal highs' in the UK: identification and formation of novel cathinones". Drug Testing and Analysis. 3 (9): 569–575. doi:10.1002/dta.204. PMID 21960541.
8. "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals" (PDF). U.S. Department of Justice. February 2023. Retrieved 5 March 2023.