Methylenedioxydimethylamphetamine

For the opioid known as 6-MDDM, see 6-Methylenedihydrodesoxymorphine.

3,4-Methylenedioxy-N,N-dimethylamphetamine (MDDM, MDDMA), 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.^[1][2] It is the N,N-dimethyl analogue of 3,4-methylenedioxyamphetamine (MDA) and the N-methyl derivative of MDMA.^[1]

MDDM

Clinical data
Other names	3,4-Methylenedioxy-N,N-dimethylamphetamine; 3,4-Methylenedioxy-(α,N,N-trimethyl)-1-ethane; MDDM; MDDMA; N,N-Dimethyl-MDA; N-Methyl-MDMA
Routes of administration	Oral[1]
Drug class	Serotonin releasing agent; Psychoactive drug
ATC code	None
Pharmacokinetic data
Duration of action	Unknown[1]
Identifiers
IUPAC name 1-(2H-1,3-benzodioxol-5-yl)-N,N-dimethylpropan-2-amine
CAS Number	74698-50-3 Y
PubChem CID	551630
ChemSpider	479880 N
UNII	L6K8DR1S8O
CompTox Dashboard (EPA)	DTXSID701024545
Chemical and physical data
Formula	C12H17NO2
Molar mass	207.273 g·mol−1
3D model (JSmol)	Interactive image
Melting point	172 to 173 °C (342 to 343 °F)
SMILES CC(Cc1ccc2c(c1)OCO2)N(C)C
InChI InChI=1S/C12H17NO2/c1-9(13(2)3)6-10-4-5-11-12(7-10)15-8-14-11/h4-5,7,9H,6,8H2,1-3H3 N Key:JEJGUIDNYBAPGN-UHFFFAOYSA-N N
NY (what is this?)  (verify)

This compound 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.^[3][4][5]

Besides being an impurity, MDDM was described as a possible novel designer drug in 2025.^[6]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists MDDM's dose as greater than 150 mg orally and its duration as unknown.^[1] Findings on the effects of MDDM are very mixed.^[1] In two reports, with 150 mg and 1,000 mg both orally, no effects whatsoever occurred.^[1] In another report, 550 mg orally resulted in very negative effects.^[1] Finally, two people who used 200 mg orally found that it produced very pleasant effects for 20 minutes, wore off, but then resurged to produce even stronger effects 4 hours later.^[1] The higher-dose reports were communicated to Shulgin anonymously and he was uncertain whether the actual substance employed was indeed MDDM.^[1] More research seems necessary to characterize MDDM, but Shulgin expected that a "pretty hefty dose" would be required for it to produce effects.^[1]

Pharmacology

Pharmacodynamics

MDDM shows reduced potency as a monoamine releasing agent and reuptake inhibitor compared to MDA and MDMA.^[2] It was 11-fold less potent than MDMA and 4-fold less potent than MDA as a serotonin releasing agent (SRA).^[2] Moreover, whereas MDA and MDMA are serotonin–norepinephrine–dopamine releasing agents (SNDRAs), MDDM is a selective SRA along with ≥10-fold weaker dopamine and norepinephrine reuptake inhibition.^[2] The related drug MDTMA is completely inactive as a monoamine releasing agent, though it does still show very weak monoamine reuptake inhibition.^[2] 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.^[7][8][9]

Society and culture

Legal status

United Kingdom

This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.^[10]

See also

• Substituted methylenedioxyphenethylamine
• MDTMA (N,N,N-trimethyl-MDA)
• Dimethylone (βk-MDDM)