2-Methylmethcathinone
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| Formula | C11H15NO |
| Molar mass | 177.247 g·mol−1 |
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2-Methylmethcathinone (2-MMC, 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 and 4-methylmethcathinone (mephedrone).[2][3] It was first identified in Sweden in 2014,[4] and has subsequently been reported in other European countries such as Poland[5] and Spain.[6]
Chemistry
[edit]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.
Pharmacology
[edit]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.[7]
| DAT | NET | SERT |
|---|---|---|
| 80 ± 8 | 53 ± 4 | 490 ± 15 |
Legal status
[edit]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).[8] 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
[edit]- 2-CMC
- 2-Me-PVP
- 3-CMC
- 3-MMC
- Ortetamine (2-Methylamphetamine)
References
[edit]- ↑ 21 CFR Part 1308 - Schedules of Controlled Substances
- ↑ 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.
- ↑ 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.
- ↑ "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.
- ↑ 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.
- ↑ 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) - ↑ 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.
- ↑ Anlage NpSG
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