2-Methylmethcathinone

2-Methylmethcathinone
Clinical data
Other names2-MMC; 2Me-MC; Ortomephedrone
Drug classStimulant; Serotonin–norepinephrine–dopamine releasing agent (SNDRA)
Legal status
Legal status
Identifiers
  • 1-(2-methylphenyl)-2-(methylamino)propan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H15NO
Molar mass177.247 g·mol−1
3D model (JSmol)
  • CC1=CC=CC=C1C(=O)C(C)NC
  • InChI=1S/C11H15NO/c1-8-6-4-5-7-10(8)11(13)9(2)12-3/h4-7,9,12H,1-3H3
  • Key:PRGXFAWAMOFULD-UHFFFAOYSA-N

2-Methylmethcathinone (2-MMC), also known as ortomephedrone, is a recreational designer drug with stimulant and euphoric effects. It is a substituted cathinone derivative, closely related to better known drugs such as 3-methylmethcathinone (3-MMC; metaphedrone) and 4-methylmethcathinone (mephedrone). It was first identified in Sweden in 2014, and has subsequently been reported in other European countries such as Poland and Spain.

Pharmacology

Pharmacodynamics

2-MMC is a serotonin-norepinephrine-dopamine releasing agent, with higher preference for the norepinephrine and dopamine transporters. 2-MMC is expected to have similar characteristics to other cathinones, although studies show 2-substituted cathinones are weaker compared to 3 and 4-substituted ones. This is potentially due to steric hindrance.

In a study comparing various aryl-substituted methcathinone analogs in rat brain synaptosomes, the following values were found.

EC50 at MATsTooltip monoamine transporters (nM)
DAT NET SERT
81 ± 853 ± 4490 ± 15

Chemistry

2-Methylmethcathinone's chemical name is 2-(methylamino)-1-phenylpropan-1-one. It is one of many substituted cathinones, synthetic chemicals derived from the natural chemical cathinone, found in khat. 2-MMC is a positional isomer of 3-MMC and 4-MMC.

Society and culture

Popularity

2-MMC has been commonly sold as a replacement for 3-MMC (3-methylmethcathinone) due to controls in the Netherlands that affect its availability, among other factors. 3-CMC was initially sold as a popular replacement for it starting in 2022, but it is now less common on the market.

The European Union Drugs Agency reported that half of the samples they received in 2024 which were sold as 3-MMC contained 2-MMC. However, despite it being known as a substitute for 3-MMC, it can be found sold in its own right.

2-MMC is controlled as a schedule I substance in the United States (under hallucinogenic substances) as it is a positional isomer of 4-MMC.

2-MMC is controlled in Germany under the NpSG (New Psychoactive Substances Act). Selling, production with the purpose of sale, and administration are punishable. Possession is illegal, but not penalized.

2-MMC is illegal in Poland. Although it is not included in the list of psychotropic substances, it falls under the group of psychotropic substances of group I-P as an isomer of 3-MMC and 4-MMC (mephedrone).

It is illegal in the United Kingdom as a class B drug.

See also

References

  1. ↑ 21 CFR Part 1308 - Schedules of Controlled Substances
  2. ↑ Maas A, Sydow K, Madea B, Hess C (April 2017). "Separation of ortho, meta and para isomers of methylmethcathinone (MMC) and methylethcathinone (MEC) using LC-ESI-MS/MS: Application to forensic serum samples". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 1051: 118–125. doi:10.1016/j.jchromb.2017.01.046. PMID 28262446.
  3. ↑ Nowak PM, Woźniakiewicz M, Mitoraj M, Sagan F, Kościelniak P (March 2018). "Thermodynamics of acid-base dissociation of several cathinones and 1-phenylethylamine, studied by an accurate capillary electrophoresis method free from the Joule heating impact". Journal of Chromatography A. 1539: 78–86. doi:10.1016/j.chroma.2018.01.047. PMID 29409596.
  4. ↑ "Europol 2014 Annual Report on the implementation of Council Decision 2005/387/JHA" (PDF). European Monitoring Centre for Drugs and Drug Addiction. 10 May 2005.
  5. ↑ Adamowicz P, Gieroń J, Gil D, Lechowicz W, Skulska A, Tokarczyk B (January 2016). "The prevalence of new psychoactive substances in biological material - a three-year review of casework in Poland". Drug Testing and Analysis. 8 (1): 63–70. doi:10.1002/dta.1924. PMID 26666629.
  6. ↑ Hart CL (2021). Drug use for grown-ups : chasing liberty in the land of fear. New York. ISBN 978-1-101-98164-1.{{cite book}}: CS1 maint: location missing publisher (link)
  7. ↑ Walther D, Shalabi AR, Baumann MH, Glennon RA (January 2019). "Systematic Structure-Activity Studies on Selected 2-, 3-, and 4-Monosubstituted Synthetic Methcathinone Analogs as Monoamine Transporter Releasing Agents". ACS Chem Neurosci. 10 (1): 740–745. doi:10.1021/acschemneuro.8b00524. PMC 8269283. PMID 30354055.
  8. 1 2 3 "European Drug Report 2025: Trends and Developments". www.euda.europa.eu. European Union Drugs Agency.
  9. ↑ Anlage NpSG