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Dimethylamphetamine

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Title: Dimethylamphetamine  
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Subject: Etilamfetamine, Fencamine, 3,4-Dimethylmethcathinone, 3-Fluoromethcathinone, 3-Fluoroethamphetamine
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Dimethylamphetamine

Dimethylamphetamine
Systematic (IUPAC) name
N,N-dimethyl-1-phenylpropan-2-amine
Clinical data
Legal status
Routes Oral
Identifiers
CAS number  YesY
ATC code None
PubChem
ChemSpider  YesY
Chemical data
Formula C11H17N 
Mol. mass 163.259 g/mol
 YesY   

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]

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 (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


Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
Phenylalkylpyrrolidines
Catecholamines
(and close relatives)
Miscellaneous


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