Methylenedioxycathinone

Methylenedioxycathinone
Clinical data
Other namesMDC; MDCATH; Normethylone; N-Desmethylmethylone; Desmethylone; β-Keto-3,4-methylenedioxyamphetamine; β-Keto-MDA; βk-MDA; Nitrilone; Amylone
Routes of
administration		Oral, Insufflation, Rectal
Drug classSerotonin–norepinephrine–dopamine releasing agent (SNDRA)
ATC code
  • None
Legal status
Legal status
Identifiers
  • (±)-2-amino-1-(3,4-methylenedioxyphenyl)propan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H11NO3
Molar mass193.202 g·mol−1
3D model (JSmol)
  • NC(C(=O)C1=CC2=C(C=C1)OCO2)C
  • InChI=1S/C10H11NO3/c1-6(11)10(12)7-2-3-8-9(4-7)14-5-13-8/h2-4,6H,5,11H2,1H3
  • Key:XDEZOLVDJWWXRG-UHFFFAOYSA-N
  (verify)

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.

Monoamine release of MDC and related agents (EC50Tooltip Half maximal effective concentration, nM)
Compound 5-HTTooltip Serotonin NETooltip Norepinephrine DATooltip Dopamine Ref
Dextroamphetamine 698–1,765 6.6–7.2 5.8–24.8
Dextromethamphetamine 736–1,292 12.3–13.8 8.5–24.5
MDATooltip Methylenedioxyamphetamine 160–162 47–108 106–190
MDMATooltip Methylenedioxymethamphetamine 49.6–72 54.1–110 51.2–278
Cathinone 6,100–7,595 23.6–25.6 34.8–83.1
Methcathinone 2,592–5,853 22–26.1 12.5–49.9
MDCTooltip Methylenedioxycathinone 966 394 370
Methylone (MDMC) 234–708 140–270 117–220
Mephedrone 118.3–122 58–62.7 49.1–51
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:
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