Dimethylamphetamine

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Dimethylamphetamine
Dimethylamphetamine.svg
Systematic (IUPAC) name
N,N-dimethyl-1-phenylpropan-2-amine
Clinical data
Legal status
Routes of
administration		 Oral
Identifiers
CAS Number 4075-96-1 YesY
ATC code none
PubChem CID: 541869
ChemSpider 471861 YesY
Chemical data
Formula C11H17N
Molecular mass 163.259 g/mol
  • CC(N(C)C)CC1=CC=CC=C1
  • InChI=1S/C11H17N/c1-8-5-4-6-11(10(8)3)7-9(2)12/h4-6,9H,7,12H2,1-3H3 YesY
  • Key:HOBBTQMIPDOWRL-UHFFFAOYSA-N YesY
  (verify)

Dimethylamphetamine (Metrotonin), also known as dimetamfetamine (INN) 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

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  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 (Berlin). 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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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