Methylenedioxydimethylamphetamine

Last updated

MDDM
MDDM.png
Clinical data
Other names3,4-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
  • 1-(2H-1,3-benzodioxol-5-yl)-N,N-dimethylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C12H17NO2
Molar mass 207.273 g·mol−1
3D model (JSmol)
Melting point 172 to 173 °C (342 to 343 °F)
  • CC(Cc1ccc2c(c1)OCO2)N(C)C
  • 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 X mark.svgN
  • Key:JEJGUIDNYBAPGN-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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]

Contents

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

United Kingdom

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

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628. https://erowid.org/library/books_online/pihkal/pihkal105.shtml
  2. 1 2 3 4 5 Sandtner W, Stockner T, Hasenhuetl PS, Partilla JS, Seddik A, Zhang YW, et al. (January 2016). "Binding Mode Selection Determines the Action of Ecstasy Homologs at Monoamine Transporters". Mol Pharmacol. 89 (1): 165–175. doi:10.1124/mol.115.101394. PMC   4702095 . PMID   26519222.
  3. ↑ Casteele SR, Bouche MP, Van Bocxlaer JF (September 2005). "LC-MS/MS in the elucidation of an isomer of the recreational drug methylenedioxy ethylamphetamine: methylenedioxy dimethylamphetamine". Journal of Separation Science. 28 (14): 1729–1734. doi:10.1002/jssc.200500108. PMID   16224967.
  4. ↑ De Letter EA, Lambert WE, Bouche MP, Cordonnier JA, Van Bocxlaer JF, Piette MH (July 2007). "Postmortem distribution of 3,4-methylenedioxy-N,N-dimethyl-amphetamine (MDDM or MDDA) in a fatal MDMA overdose". International Journal of Legal Medicine. 121 (4): 303–307. doi:10.1007/s00414-006-0094-x. PMID   16636864.
  5. ↑ Awad T, Belal T, Maher HM, DeRuiter J, Clark CR (October 2010). "GC-MS studies on side chain regioisomers related to substituted methylenedioxyphenethylamines: MDEA, MDMMA, and MBDB". Journal of Chromatographic Science. 48 (9): 726–732. doi:10.1093/chromsci/48.9.726. PMID   20875234.
  6. ↑ Byrska B, Masier K, Stanaszek R (November 2025). ""New kid on the block"-MDDM as a new ingredient in Ecstasy tablets". J Forensic Sci. doi:10.1111/1556-4029.70226. PMID   41254475.
  7. ↑ Dettmeyer R, Verhoff MA, Schütz HF (9 October 2013). Forensic Medicine: Fundamentals and Perspectives. Springer Science & Business Media. p. 519. ISBN   978-3-642-38818-7. Table 30.13: Amphetamine Data [...] Note: So-called prodrugs, such as amphetaminil (psychoanaleptic), benzphetamine, clobenzorex, dimethylamphetamine, ethylamphetamine, famprofazone, fencamine, fenethylline, fenproporex, furfenorex, mefenorex, mesocarb, prenylamine, and selegiline (antiparkinson agent), can result in the production of methamphetamine or amphetamine in the organism
  8. ↑ Cody JT (May 2002). "Precursor medications as a source of methamphetamine and/or amphetamine positive drug testing results". J Occup Environ Med. 44 (5): 435–450. doi:10.1097/00043764-200205000-00012. PMID   12024689.
  9. ↑ Inoue T, Suzuki S (August 1987). "The metabolism of dimethylamphetamine in rat and man". Xenobiotica. 17 (8): 965–971. doi:10.3109/00498258709044195. PMID   3673111.
  10. ↑ "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design. Archived from the original on 22 October 2017. Retrieved 12 March 2014.
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