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Methylenedioxycathinone

Chemical compound

3,4-Methylenedioxycathinone (MDC, MDCATH), also known as β-keto-3,4-methylenedioxyamphetamine (β-keto-MDA or βk-MDA), is an entactogen and stimulant drug of the phenethylamine, amphetamine, and cathinone families related to methylone (βk-MDMA or MDMC). It is the β-keto analogue of MDA.

Like methylone, MDC is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In contrast to MDA and MDMA, MDC shows no activity at the serotonin 5-HT2 receptors, but does retain much weaker affinity for the rodent trace amine-associated receptor 1 (TAAR1).

The drug was patented as an antidepressant and antiparkinsonian agent by Peyton Jacob III and Alexander Shulgin in 1996. MDC and other non-N-substituted cathinones such as cathinone itself are chemically unstable due rapidly forming biologically inactive dimers and this has limited their prevalence.

Compound	Ref
Dextroamphetamine	698–1,765
Dextromethamphetamine	736–1,292
	160–162
	49.6–72
Cathinone	6,100–7,595
Methcathinone	2,592–5,853
	966
Methylone (MDMC)	234–708
Mephedrone	118.3–122
Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs:

References

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(December 1997). "Cathinone: an investigation of several N-alkyl and methylenedioxy-substituted analogs". Pharmacology, Biochemistry, and Behavior.
Dal Cason, Terry A. (May 1997). "The characterization of some 3,4-methylenedioxycathinone (MDCATH) homologs". Forensic Science International.
(July 2015). "Pharmacological profile of novel psychoactive benzofurans". British Journal of Pharmacology.
"Preparation of novel N-substituted-2-amino-3′,4′-methylenedioxypropiophenones as anti-depressant and anti-parkinsonism agents.".
(January 2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse.
(2013). "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology.
(2012). "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology.
(July 2008). "Dopamine Transporters: Chemistry, Biology and Pharmacology". Wiley.
(February 2016). "The new psychoactive substances 5-(2-aminopropyl)indole (5-IT) and 6-(2-aminopropyl)indole (6-IT) interact with monoamine transporters in brain tissue". Neuropharmacology.
(June 2003). "3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro". Molecular Pharmacology.
(December 2020). "The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats". Psychopharmacology (Berl).
(March 2019). "The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes". Psychopharmacology.
(March 2024). "Structure-activity relationships for locomotor stimulant effects and monoamine transporter interactions of substituted amphetamines and cathinones". Neuropharmacology.
Shalabi, Abdelrahman R.. (14 December 2017). "Structure-Activity Relationship Studies of Bupropion and Related 3-Substituted Methcathinone Analogues at Monoamine Transporters".
(January 2019). "Systematic Structure-Activity Studies on Selected 2-, 3-, and 4-Monosubstituted Synthetic Methcathinone Analogs as Monoamine Transporter Releasing Agents". ACS Chem Neurosci.
Sakloth, Farhana. (11 December 2015). "Psychoactive synthetic cathinones (or 'bath salts'): Investigation of mechanisms of action".
(April 2021). "Eutylone and Its Structural Isomers Interact with Monoamine Transporters and Induce Locomotor Stimulation". ACS Chem Neurosci.
(February 2017). "Pharmacokinetic Profiles and Pharmacodynamic Effects for Methylone and Its Metabolites in Rats". Neuropsychopharmacology.
(May 2015). "Quantitative structure-activity relationship analysis of the pharmacology of para-substituted methcathinone analogues". Br J Pharmacol.
(October 2003). "Monoamine transporters and psychostimulant drugs". Eur J Pharmacol.
(2006). "Therapeutic potential of monoamine transporter substrates". Current Topics in Medicinal Chemistry.

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cathinones entactogens euphoriants methylenedioxyphenethylamines serotonin-norepinephrine-dopamine-releasing-agents taar1-modulators

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