Misplaced Pages

Dimethylamphetamine

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Chemical compound Pharmaceutical compound
Dimethylamphetamine
INN: Dimetamfetamine
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
Identifiers
IUPAC name
  • N,N-dimethyl-1-phenylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H17N
Molar mass163.264 g·mol
3D model (JSmol)
SMILES
  • CC(N(C)C)CC1=CC=CC=C1
InChI
  • InChI=1S/C11H17N/c1-10(12(2)3)9-11-7-5-4-6-8-11/h4-8,10H,9H2,1-3H3
  • Key:OBDSVYOSYSKVMX-UHFFFAOYSA-N
  (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 and less neurotoxic compared to methamphetamine. However, it still retains some mild stimulant effects and abuse potential, 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.

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

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.
Stimulants
Adamantanes
Adenosine antagonists
Alkylamines
Ampakines
Arylcyclohexylamines
Benzazepines
Cathinones
Cholinergics
Convulsants
Eugeroics
Oxazolines
Phenethylamines
Phenylmorpholines
Piperazines
Piperidines
Pyrrolidines
Racetams
Tropanes
Tryptamines
Others
ATC code: N06B
Monoamine releasing agents
DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
Others
See also: Receptor/signaling modulatorsMonoamine reuptake inhibitorsAdrenergicsDopaminergicsSerotonergicsMonoamine metabolism modulatorsMonoamine neurotoxins
Phenethylamines
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
Phenylalkylpyrrolidines
Catecholamines
(and close relatives)
Miscellaneous
Categories: