Methylone (also known as “3,4-methylenedioxy-N-methylcathinone“, “MDMC“, “βk-MDMA” and by the slang term “M1“) is an empathogen and stimulant psychoactive drug. It is a member of the substituted amphetamine, substituted cathinone and substituted methylenedioxyphenethylamine classes.
Methylone is the substituted cathinone analog of MDMA and the 3,4-methylenedioxy analog of methcathinone. The only structural difference of methylone with respect to MDMA is the substitution of 2 hydrogen atoms by 1 oxygen atom in the β position of the phenethylamine core, forming a ketone group..
Methylone was first synthesized by the chemists Peyton Jacob III and Alexander Shulgin in 1996 for potential use as an antidepressant.. Methylone has been sold for recreational use, taking advantage of the absence of legal prohibition of this compound in many countries.
Methylone, or 3,4-methylenedioxy-N-methylcathinone, is a synthetic molecule of the cathinone family. Cathinones are structurally similar to amphetamines, they contain a phenethylamine core featuring a phenyl ring bound to an amino (NH2) group through an ethyl chain with an additional methyl substitution at Rα. Cathinones such as methylone are alpha-methylated phenethylamines. Cathinones differ from amphetamines by the addition of a ketone functional group, a carbonyl group at Rβ.
Methylone contains an methyl substitution at RN, a substitution which is shared with MDMA, mephedrone, and certain other stimulants. Methylone contains additional substitutions at R3 and R4 of the phenyl ring with oxygen groups. These oxygen groups are incorporated into a methylenedioxy ring through a methylene chain. Methylone shares this methylenedioxy ring with MDA, MDAI and MDMA.
Methylone acts as a mixed reuptake inhibitor/releasing agent of serotonin, norepinephrine, and dopamine.. These neurotransmittersare thought to be responsible for regulating pleasure, motivation, focus, and sense of well-being. This is done by inhibiting the reuptake and reabsorption of the neurotransmitters after they have performed their function of transmitting a neural impulse, allowing them to accumulate and be reused, which results stimulating and euphoric effects.
In comparison to MDMA, it has approximately 3x lower affinity for the serotonin transporter (Ki=242.1 nM for methylone to Ki=72 nM for MDMA) while its affinity for the norepinephrine and dopamine transporters is similar.. Notably, methylone’s affinity for the vesicular monoamine transporter 2 (VMAT2) is about 13x lower than that of MDMA..
The result of these differences in pharmacology relative to MDMA are that methylone is less potent in terms of dose, has more balanced catecholaminergic relative to serotonergic effects, and behaves more like a reuptake inhibitor such as methylphenidate rather than a releaser like amphetamine; however, methylone still has relatively robust releasing capabilities..
|Common names||Methylone, bk-MDMA, M1, MDMC|
|Psychoactive class||Stimulant / Entactogen|
|Chemical class||Cathinone / MDxx|
|Routes of Administration|