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Dimethylamphetamine

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This is an old revision of this page, as edited by Tillbury (talk | contribs) at 01:55, 29 June 2018 (InChI and Key corrected to match the structure depicted, i.e. with the stereochemistry of the α-methyl undefined. The previous values encoded an isomer, 2,3-Dimethylamphetamine. Pubchem and Chemspider also changed to match the InChI). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Dimethylamphetamine
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
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H17N
Molar mass163.259 g/mol 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 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 a Schedule I controlled drug.

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 methylation of amphetamine 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. Behavioral effects of N-methylamphetamine and N,N-dimethylamphetamine in rats and squirrel monkeys. Journal of Pharmacology and Experimental Therapeutics. 1990 May;253(2):466-74.
  2. ^ Ricaurte GA, DeLanney LE, Irwin I, Witkin JM, Katz JL, Langston JW. Evaluation of the neurotoxic potential of N,N-dimethylamphetamine: an illicit analog of methamphetamine. Brain Research. 1989 Jun 26;490(2):301-6.
  3. ^ Fasciano J, Hatzidimitriou G, Yuan J, Katz JL, Ricaurte GA. N-methylation dissociates methamphetamine's neurotoxic and behavioral pharmacologic effects. Brain Research. 1997 Oct 10;771(1):115-20.
  4. ^ Katz JL, Ricaurte GA, Witkin JM. Reinforcing effects of enantiomers of N,N-dimethylamphetamine in squirrel monkeys. Psychopharmacology. 1992;107(2-3):315-8.
  5. ^ US Drug Enforcement Administration: Microgram Bulletin
  6. ^ US Drug Enforcement Administration: The Identification of d-N,N-Dimethylamphetamine (DMA) in an Exhibit in Malaysia
  7. ^ Reinhard Dettmeyer; Marcel A. Verhoff; Harald F. Schütz (9 October 2013). Forensic Medicine: Fundamentals and Perspectives. Springer Science & Business Media. pp. 519–. ISBN 978-3-642-38818-7.


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