Methylenedioxycathinone

Chemical compound From Wikipedia, the free encyclopedia

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).[1][2][3] It is the β-keto analogue of MDA.[4]

Other namesMDC; MDCATH; Normethylone; N-Desmethylmethylone; Desmethylone; β-Keto-3,4-methylenedioxyamphetamine; β-Keto-MDA; βk-MDA; Nitrilone; Amylone
Routes of
administrationOral, Insufflation, Rectal
Drug classSerotonin–norepinephrine–dopamine releasing agent (SNDRA)
ATC code
  • None
Quick facts Clinical data, Other names ...
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)
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Like methylone, MDC is a serotonin–norepinephrine–dopamine releasing agent (SNDRA).[5][6] 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).[6]

The drug was patented as an antidepressant and antiparkinsonian agent by Peyton Jacob III and Alexander Shulgin in 1996.[7] 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.[1]

More information Compound, 5-HTTooltip Serotonin ...
Monoamine release of MDC and related agents (EC50Tooltip Half maximal effective concentration, nM)
Compound5-HTTooltip SerotoninNETooltip NorepinephrineDATooltip DopamineRef
Dextroamphetamine698–1,7656.6–7.25.8–24.8[8][9]
Dextromethamphetamine736–1,29212.3–13.88.5–24.5[8][10]
MDATooltip Methylenedioxyamphetamine160–16247–108106–190[11][12][13]
MDMATooltip Methylenedioxymethamphetamine49.6–7254.1–11051.2–278[8][10][14][11][13]
Cathinone6,100–7,59523.6–25.634.8–83.1[12][15][16]
Methcathinone2,592–5,85322–26.112.5–49.9[12][15][17][18][16]
MDCTooltip Methylenedioxycathinone966394370[5]
Methylone (MDMC)234–708140–270117–220[10][9][19][20][5]
Mephedrone118.3–12258–62.749.1–51[10][9][15][18][21]
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:[22][23]
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References

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