3-Methylmethcathinone

3-Methylmethcathinone
Clinical data
Other names	3-MMC; Metaphedrone; 3-Methyl-N-methylcathinone; 3,N-Dimethylcathinone; 3,N-Dimethyl-β-ketoamphetamine; 3,α,N-Trimethyl-β-ketophenethylamine
ATC code	None;
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); DE: Anlage I (Authorized scientific use only); UK: Class B; US: Schedule I; UN: Psychotropic Schedule II;
Pharmacokinetic data
Bioavailability	Oral: 5–9%
Protein binding	Low
Elimination half-life	50 min (in pigs)
Identifiers
	IUPAC name 2-(Methylamino)-1-(3-methylphenyl)propan-1-one;
CAS Number	1246911-86-3 ;
PubChem CID	71741532;
ChemSpider	34445939;
UNII	73Q9QTO1N4;
KEGG	C22828 ;
CompTox Dashboard (EPA)	DTXSID401043421 ;
ECHA InfoCard	100.259.777
Chemical and physical data
Formula	C11H15NO
Molar mass	177.247 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	193.2 °C (379.8 °F) ± 0.2°C (hydrochloride salt)
Boiling point	280.5 °C (536.9 °F) ± 23.0°C at 760 mm Hg
Solubility in water	Sparingly soluble in PBS; slightly soluble in ethanol, dimethyl sulfoxide, and dimethyl formamide. mg/mL (20 °C)
	SMILES CC1=CC=CC(C(C(C)NC)=O)=C1;
	InChI InChI=1S/C11H15NO/c1-8-5-4-6-10(7-8)11(13)9(2)12-3/h4-7,9,12H,1-3H3; Key:QDNXSIYWHYGMCD-UHFFFAOYSA-N;

3-Methylmethcathinone (3-MMC), also known as metaphedrone,^[4] is a designer drug from the substituted cathinone family. 3-MMC is a monoamine transporter substrate (a substance acted upon by monoamine transporters) that potently releases and inhibits the reuptake of dopamine and norepinephrine, as well as displaying moderate serotonin releasing activity.^[5] Unlike some synthetic cathinones, 3-MMC has been evaluated in at least one large mammal study.^[2]

3-Methylmethcathinone is a structural isomer of mephedrone (4-methylmethcathinone), and as such is illegal via blanket bans in many countries that have banned mephedrone. However, 3-MMC has still appeared on the recreational drug market as an alternative to mephedrone, and was first identified being sold in Sweden in 2012.^[6]

^ Cite error: The named reference unodc was invoked but never defined (see the help page).
^ ^a ^b ^c ^d Shimshoni JA, Britzi M, Sobol E, Willenz U, Nutt D, Edery N (June 2015). "3-Methyl-methcathinone: Pharmacokinetic profile evaluation in pigs in relation to pharmacodynamics". Journal of Psychopharmacology. 29 (6): 734–43. doi:10.1177/0269881115576687. PMID 25804420. S2CID 26012927.
^ "3-Methylmethcathinone (3-MMC) Critical Review Report" (PDF). World Health Organization. Archived from the original (PDF) on 11 November 2021.
^ Preedy V (26 April 2016). Neuropathology of Drug Addictions and Substance Misuse Volume 2: Stimulants, Club and Dissociative Drugs, Hallucinogens, Steroids, Inhalants and International Aspects (2 ed.). London: King's College. ISBN 978-0-12-800212-4.
^ Luethi D, Kolaczynska KE, Docci L, Krähenbühl S, Hoener MC, Liechti ME (May 2018). "Pharmacological profile of mephedrone analogs and related new psychoactive substances" (PDF). Neuropharmacology. 134 (Pt A): 4–12. doi:10.1016/j.neuropharm.2017.07.026. PMID 28755886. S2CID 28786127.
^ "EMCDDA 2012 Annual report on the state of the drugs problem in Europe" (PDF). Archived from the original (PDF) on 23 April 2014. Retrieved 17 April 2014.

[unodc-1] Cite error: The named reference unodc was invoked but never defined (see the help page).

[metaphedrone2015-2] Shimshoni JA, Britzi M, Sobol E, Willenz U, Nutt D, Edery N (June 2015). "3-Methyl-methcathinone: Pharmacokinetic profile evaluation in pigs in relation to pharmacodynamics". Journal of Psychopharmacology. 29 (6): 734–43. doi:10.1177/0269881115576687. PMID 25804420. S2CID 26012927.

[WHO_3MMC-3] "3-Methylmethcathinone (3-MMC) Critical Review Report" (PDF). World Health Organization. Archived from the original (PDF) on 11 November 2021.

[4] Preedy V (26 April 2016). Neuropathology of Drug Addictions and Substance Misuse Volume 2: Stimulants, Club and Dissociative Drugs, Hallucinogens, Steroids, Inhalants and International Aspects (2 ed.). London: King's College. ISBN 978-0-12-800212-4.

[Luethi_2018-5] Luethi D, Kolaczynska KE, Docci L, Krähenbühl S, Hoener MC, Liechti ME (May 2018). "Pharmacological profile of mephedrone analogs and related new psychoactive substances" (PDF). Neuropharmacology. 134 (Pt A): 4–12. doi:10.1016/j.neuropharm.2017.07.026. PMID 28755886. S2CID 28786127.

[6] "EMCDDA 2012 Annual report on the state of the drugs problem in Europe" (PDF). Archived from the original (PDF) on 23 April 2014. Retrieved 17 April 2014.

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