3-Methoxymethcathinone
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| Other names | 3-MeOMC; meta-Methoxymethcathinone; m-MeOMC; 3-Methoxy-N-methylcathinone; 3-Methoxy-N-methyl-β-ketoamphetamine; 3-Methoxy-α,N-dimethyl-β-ketophenethylamine |
| Drug class | Serotonin–dopamine releasing agent; Serotonin–norepinephrine–dopamine releasing agent; Stimulant[1][2] |
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| Formula | C11H15NO2 |
| Molar mass | 193.246 g·mol−1 |
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3-Methoxymethcathinone (3-MeOMC), also known as meta-methoxymethcathinone (m-MeOMC), is a designer drug of the substituted cathinone family described as a stimulant.[3][2][1]
Similarly to other cathinones, it acts as a monoamine releasing agent, including of serotonin, dopamine, and norepinephrine.[1][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).[1] Its EC50 values are 129 nM for dopamine release and 306 nM for serotonin release in vitro, whereas it only induced 68% release of norepinephrine at a concentration of 10 μM.[1][4][5] 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 10 μM.[1] However, in another publication, the EC50 of 3-MMC for induction of norepinephrine release was 111 nM, 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).[4][5]
3-MeOMC first appeared as an illicit drug after 2014.[3]
See also
[edit]- 2-Fluoromethcathinone (2-FMC)
References
[edit]- ^ a b c d e f Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, et al. (March 2019). "The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes". Psychopharmacology (Berl). 236 (3): 915–924. doi:10.1007/s00213-018-5063-9. PMC 6475490. PMID 30341459.
- ^ a b Awuchi CG, Aja MP, Mitaki NB, Morya S, Amagwula IO, Echeta CK, et al. (2 February 2023). "New Psychoactive Substances: Major Groups, Laboratory Testing Challenges, Public Health Concerns, and Community-Based Solutions". Journal of Chemistry. 2023. Wiley: 1–36. doi:10.1155/2023/5852315. ISSN 2090-9071.
- ^ a b Carroll FI, Lewin AH, Mascarella SW, Seltzman HH, Reddy PA (April 2021). "Designer drugs: a medicinal chemistry perspective (II)". Ann N Y Acad Sci. 1489 (1): 48–77. Bibcode:2021NYASA1489...48C. doi:10.1111/nyas.14349. PMID 32396701.
- ^ a b c Shalabi AR (14 December 2017). "Structure-Activity Relationship Studies of Bupropion and Related 3-Substituted Methcathinone Analogues at Monoamine Transporters". VCU Scholars Compass. Retrieved 24 November 2024.
- ^ a b c 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.