3,4-Ethylenedioxymethcathinone
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| Other names | EDMC; Ethylenedioxymethcathinone; 3,4-Ethylenedioxy-N-methylcathinone; β-Keto-EDMA; BK-EDMA; βk-EDMA |
| Drug class | Serotonin–norepinephrine–dopamine releasing agent |
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| Formula | C12H15NO3 |
| Molar mass | 221.256 g·mol−1 |
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3,4-Ethylenedioxymethcathinone (EDMC), or 3,4-ethylenedioxy-N-methylcathinone, is a monoamine releasing agent (MRA) of the cathinone family related to methylone (3,4-methylenedioxymethcathinone; MDMC).[1][2][3][4] It is the β-keto or cathinone analogue of 3,4-ethylenedioxymethamphetamine (EDMA).[1][2]
EDMC acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA).[3][1][2] Its EC50 values for induction of monoamine release are 347 nM for serotonin, 327 nM for norepinephrine, and 496 nM for dopamine in rat brain synaptosomes.[1][2] These potencies were about 1.4-fold, 2.2-fold, and 3.7-fold lower than those of methylone, respectively.[1][2]
The drug was first described in 2015, whereas EDMA has been described much earlier.[1][2]
See also
[edit]- 3,4-Ethylenedioxyamphetamine (EDA)
- 3,4-Ethylidenedioxyamphetamine (EIDA)
- 3,4-Isopropylidenedioxyamphetamine (IDA)
References
[edit]- ^ a b c d e f Del Bello F, Sakloth F, Partilla JS, Baumann MH, Glennon RA (September 2015). "Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine". Bioorganic & Medicinal Chemistry. 23 (17): 5574–5579. doi:10.1016/j.bmc.2015.07.035. PMC 4562428. PMID 26233799.
- ^ a b c d e f Sakloth F (11 December 2015). Psychoactive synthetic cathinones (or 'bath salts'): Investigation of mechanisms of action (Ph.D. thesis). Virginia Commonwealth University. Retrieved 19 January 2025 – via VCU Scholars Compass.
- ^ a b Glennon RA, Dukat M (2017). "Structure-Activity Relationships of Synthetic Cathinones". Current Topics in Behavioral Neurosciences. 32: 19–47. doi:10.1007/7854_2016_41. ISBN 978-3-319-52442-9. PMC 5818155. PMID 27830576.
Expansion of the methylenedioxy ring of methylone (24) to an ethylenedioxy ring (i.e., ethylenedioxymethcathinone, EDMC; 30; Figure 7) decreased its potency as a releasing agent at all three transporters by 2- to 3-fold (Del Bello et al., 2015).
- ^ Yadav BJ (16 July 2019). Understanding Structure–Activity Relationship of Synthetic Cathinones (Bath Salts) Utilizing Methylphenidate. Theses and Dissertations (Ph.D. thesis). Virginia Commonwealth University. doi:10.25772/MJQW-8C64. Retrieved 24 November 2024 – via VCU Scholars Compass.
8 In another study conducted by Del Bello et al.89 it was found that expansion of the methylenedioxy ring of MDMC (27) to an ethylenedioxy ring (EDMC, 31, Figure 14) slightly reduced its potency as a releasing agent at all three transporters.
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