Methylenedioxydimethylamphetamine
3,4-Methylenedioxy-N,''N-dimethylamphetamine, also known as N,''N-dimethyl-MDA or N-methyl-MDMA, is a lesser-known serotonin releasing agent and psychoactive drug of the phenethylamine, amphetamine, and MDxx families. It is the N,''N-dimethyl analogue of 3,4-methylenedioxyamphetamine and the N''-methyl derivative of MDMA. The drug is a known synthetic impurity of MDMA and has also been described as a possible novel designer drug in 2025.
Use and effects
In his book PiHKAL, Alexander Shulgin lists MDDM's dose as greater than 150mg orally and its duration as unknown. Findings on the effects of MDDM are very mixed. In two reports, with 150mg and 1,000mg both orally, no effects whatsoever occurred. In another report, 550mg orally resulted in very negative effects. Finally, two people who used 200mg orally found that it produced very pleasant effects for 20minutes, wore off, but then resurged to produce even stronger effects 4hours later. The higher-dose reports were communicated to Shulgin anonymously and he was uncertain whether the actual substance employed was indeed MDDM. More research seems necessary to characterize MDDM, but Shulgin expected that a "pretty hefty dose" would be required for it to produce effects.
Pharmacology
Pharmacodynamics
MDDM shows reduced potency as a monoamine releasing agent and reuptake inhibitor compared to MDA and MDMA. It was 11-fold less potent than MDMA and 4-fold less potent than MDA as a serotonin releasing agent. Moreover, whereas MDA and MDMA are serotonin–norepinephrine–dopamine releasing agents, MDDM is a selective SRA along with ≥10-fold weaker dopamine and norepinephrine reuptake inhibition. The related drug MDTMA is completely inactive as a monoamine releasing agent, though it does still show very weak monoamine reuptake inhibition. Another related drug, dimethylamphetamine, is said to be a prodrug of methamphetamine and amphetamine, although it is much less potent and weaker than these drugs.
Chemistry
Impurity
MDDM is occasionally encountered as an impurity in MDMA which has been synthesized by methylation of MDA using methylating chemical reagents such as methyl iodide. An excess of reagent or a reaction temperature that is too high results in some double methylation of the amine nitrogen, yielding MDDM as well as MDMA. The presence of MDDM as an impurity can thus reveal which synthetic route was used to manufacture seized samples of MDMA.
Analogues
Analogues of MDDM include MDTMA and dimethylone, among others.
Society and culture
Canada
MDDM is a controlled substance in Canada.
United Kingdom
This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.