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Dimethylamphetamine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Dimethylamphetamine
INN: Dimetamfetamine
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • N,N-dimethyl-1-phenylpropan-2-amine
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC11H17N
Molar mass163.264 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 checkY
  • Key:OBDSVYOSYSKVMX-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Dimethylamphetamine (Metrotonin), also known asdimetamfetamine (INN),dimephenopan andN,N-dimethylamphetamine, is astimulantdrug of thephenethylamine andamphetaminechemical classes. Dimethylamphetamine has weaker stimulant effects thanamphetamine ormethamphetamine 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 ofdextroamphetamine if the reaction temperature is too high or an excess of methylating agent is used.[5][6]

It is said to be aprodrug ofmethamphetamine andamphetamine, which are minormetabolites.[7][8][9]

See also

[edit]

References

[edit]
  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 fromthe original(PDF) on 2013-04-14. Retrieved2013-08-06.
  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. 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.

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