|Common names||Methylone, bk-MDMA, M1, MDMC|
methylone was first synthesized by chemists peyton jacob iii and alexander shulgin in 1996 as a potential antidepressant.
methylone is sometimes used as a substitute for mdma due to similarities in their effects. alexander shulgin commented that the substances has “almost the same potency of mdma, but it does not produce the same effects.” he also stated that it “has an almost antidepressant action, pleasant and positive, but not the unique magic of mdma.”
the toxicity of methylone has not been well-studied, although it likely does not exceed that of mdma, and it has a limited history of human usage. it is highly advised to use harm reduction practices if using this substance.
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 neurotransmitters are 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.
“methylone” is also a trademarked brand name for an injectable form of methylprednisolone, a corticosteroid hormone used to treat arthritis and severe allergic reactions; hence, methylone may be confused with it. aside from context, they can be distinguished by the fact that the name will usually be capitalized when referring to the prescription drug.
a proposed alternate name is bk-mdma, or beta-keto-mdma. while this nomenclature has not caught on because the name “methylone” became widely used before the conflicting methylone trademark was noticed, the analogous names for related chemicals bk-mdea and bk-mbdb have become the established names for those substances.