3-Methoxymethcathinone Explained

Class:Serotonin–dopamine releasing agent
Serotonin–norepinephrine–dopamine releasing agent; Stimulant
Cas Number:882302-56-9
Pubchem:82281626
Chemspiderid:26702454
Unii:TAS3L629HH
Synonyms:3-MeOMC; meta-Methoxymethcathinone; m-MeOMC; 3-Methoxy-N-methylcathinone; 3-Methoxy-N-methyl-β-ketoamphetamine; 3-Methoxy-α,N-dimethyl-β-ketophenethylamine
Iupac Name:1-(3-methoxyphenyl)-2-(methylamino)propan-1-one
C:11
H:15
N:1
O:2
Smiles:CC(C(=O)C1=CC(=CC=C1)OC)NC
Stdinchi:1S/C11H15NO2/c1-8(12-2)11(13)9-5-4-6-10(7-9)14-3/h4-8,12H,1-3H3
Stdinchikey:VAVRRUJYUFACKA-UHFFFAOYSA-N

3-Methoxymethcathinone (3-MeOMC), also known as meta-methoxymethcathinone (m-MeOMC), is a designer drug of the substituted cathinone family described as a stimulant.[1] [2] [3]

Similarly to other cathinones, it acts as a monoamine releasing agent, including of serotonin, dopamine, and norepinephrine.[4] [5] However, in contrast to cathinones and amphetamines, 3-MeOMC appears to show selectivity for induction of serotonin and dopamine release over release of norepinephrine, and hence may act as a partially selective serotonin–dopamine releasing agent (SDRA). Its values are 129nM for dopamine release and 306nM for serotonin release in vitro, whereas it only induced 68% release of norepinephrine at a concentration of 10μM. For comparison, other related cathinones, including cathinone, methcathinone, 3-methylmethcathinone (3-MMC; metaphedrone), 4-methylmethcathinone (4-MMC; mephedrone), and 4-methoxymethcathinone (4-MeOMC; methedrone), induced 94 to 101% release of norepinephrine at 10μM. However, in another publication, the of 3-MMC for induction of norepinephrine release was 111nM, and hence it did not appear to show selectivity for induction of serotonin and dopamine release relative to norepinephrine, instead acting as a serotonin–norepinephrine–dopamine releasing agent (SNDRA).

3-MeOMC first appeared as an illicit drug after 2014.

See also

Notes and References

  1. Carroll FI, Lewin AH, Mascarella SW, Seltzman HH, Reddy PA . Designer drugs: a medicinal chemistry perspective (II) . Ann N Y Acad Sci . 1489 . 1 . 48–77 . April 2021 . 32396701 . 10.1111/nyas.14349 . 2021NYASA1489...48C .
  2. Awuchi CG, Aja MP, Mitaki NB, Morya S, Amagwula IO, Echeta CK, Igwe VS . New Psychoactive Substances: Major Groups, Laboratory Testing Challenges, Public Health Concerns, and Community-Based Solutions . Journal of Chemistry . Wiley . 2023 . 2 February 2023 . 2090-9071 . 10.1155/2023/5852315 . free . 1–36.
  3. Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, Rothman RB . The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes . Psychopharmacology (Berl) . 236 . 3 . 915–924 . March 2019 . 30341459 . 6475490 . 10.1007/s00213-018-5063-9 .
  4. Web site: Shalabi . Abdelrahman R. . Structure-Activity Relationship Studies of Bupropion and Related 3-Substituted Methcathinone Analogues at Monoamine Transporters . VCU Scholars Compass . 14 December 2017 . 24 November 2024.
  5. Walther D, Shalabi AR, Baumann MH, Glennon RA . 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 . January 2019 . 30354055 . 8269283 . 10.1021/acschemneuro.8b00524 .