Dimethylamphetamine

Last updated
Dimethylamphetamine
INN: Dimetamfetamine
Dimethylamphetamine.svg
Dimetamfetamin.png
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • N,N-dimethyl-1-phenylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H17N
Molar mass 163.264 g·mol−1
3D model (JSmol)
  • CC(N(C)C)CC1=CC=CC=C1
  • InChI=1S/C11H17N/c1-10(12(2)3)9-11-7-5-4-6-8-11/h4-8,10H,9H2,1-3H3 Yes check.svgY
  • Key:OBDSVYOSYSKVMX-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Dimethylamphetamine (Metrotonin), also known as dimetamfetamine (INN), dimephenopan and N,N-dimethylamphetamine, is a stimulant drug of the phenethylamine and amphetamine chemical classes. Dimethylamphetamine has weaker stimulant effects than amphetamine or methamphetamine and is considerably less addictive [1] and less neurotoxic compared to methamphetamine. [2] [3] However, it still retains some mild stimulant effects and abuse potential, [4] and is illegal in both the United States and Australia.

Dimethylamphetamine has occasionally been found in illicit methamphetamine laboratories, but is usually an impurity rather than the desired product. It may be produced by accident when methamphetamine is synthesised by N-methylation of dextroamphetamine if the reaction temperature is too high or an excess of methylating agent is used. [5] [6]

It is said to be a prodrug of amphetamine/methamphetamine. [7]

References

  1. Witkin JM, Ricaurte GA, Katz JL (May 1990). "Behavioral effects of N-methylamphetamine and N,N-dimethylamphetamine in rats and squirrel monkeys". The Journal of Pharmacology and Experimental Therapeutics. 253 (2): 466–74. PMID   2338643.
  2. Ricaurte GA, DeLanney LE, Irwin I, Witkin JM, Katz JL, Langston JW (June 1989). "Evaluation of the neurotoxic potential of N,N-dimethylamphetamine: an illicit analog of methamphetamine". Brain Research. 490 (2): 301–6. doi:10.1016/0006-8993(89)90247-3. PMID   2765865. S2CID   20682993.
  3. Fasciano J, Hatzidimitriou G, Yuan J, Katz JL, Ricaurte GA (October 1997). "N-methylation dissociates methamphetamine's neurotoxic and behavioral pharmacologic effects". Brain Research. 771 (1): 115–20. doi: 10.1016/s0006-8993(97)00801-9 . PMID   9383014. S2CID   8456534.
  4. Katz JL, Ricaurte GA, Witkin JM (1992). "Reinforcing effects of enantiomers of N,N-dimethylamphetamine in squirrel monkeys". Psychopharmacology. 107 (2–3): 315–8. doi:10.1007/BF02245154. PMID   1615131. S2CID   24707878.
  5. "Microgram Bulletin" (PDF). US Drug Enforcement Administration. Archived from the original (PDF) on 2013-04-14. Retrieved 2013-08-06.
  6. "The Identification of d-N,N-Dimethylamphetamine (DMA) in an Exhibit in Malaysia" (PDF). US Drug Enforcement Administration.
  7. Dettmeyer R, Verhoff MA, Schütz HF (9 October 2013). Forensic Medicine: Fundamentals and Perspectives. Springer Science & Business Media. pp. 519–. ISBN   978-3-642-38818-7.