2-Methylmethcathinone

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]

2-Methylmethcathinone

Legal status
Legal status	UK: Class B US: Schedule I[1]
Identifiers
IUPAC name 1-(2-methylphenyl)-2-(methylamino)propan-1-one
CAS Number	1246911-71-6 Y
PubChem CID	56603536
ChemSpider	37701507
UNII	8Z237SST51
CompTox Dashboard (EPA)	DTXSID001043043
Chemical and physical data
Formula	C11H15NO
Molar mass	177.247 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC=CC=C1C(=O)C(C)NC
InChI 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

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.

Pharmacology

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]

EC50 releasing values at monoamine transporters (nM)

DAT	NET	SERT
80 ± 8	53 ± 4	490 ± 15

Legal status

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

• 2-CMC
• 2-Me-PVP
• 3-CMC
• 3-MMC
• Ortetamine (2-Methylamphetamine)