Dimethylamphetamine

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title: "Dimethylamphetamine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["designer-prodrugs", "dimethylamino-compounds", "methamphetamines", "norepinephrine-dopamine-releasing-agents", "substituted-amphetamines"] description: "Chemical compound" topic_path: "general/designer-prodrugs" source: "https://en.wikipedia.org/wiki/Dimethylamphetamine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 449577684 | drug_name = Dimethylamphetamine | INN = Dimetamfetamine | IUPAC_name = N,N-dimethyl-1-phenylpropan-2-amine | image = Dimethylamphetamine.svg | image_class = skin-invert-image | width = 200px | image2 = Dimetamfetamin.png | image_class2 = bg-transparent

| tradename = | pregnancy_category = | legal_AU = S9 | legal_US = Schedule I | routes_of_administration = Oral

| bioavailability = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 4075-96-1 | ATC_prefix = none | ATC_suffix = | UNII_Ref= | UNII= IYE3F3MHCU | PubChem = 20006 | ChemSpiderID_Ref = | ChemSpiderID = 18847 | KEGG_Ref = | KEGG = C22825

| C=11 | H=17 | N=1 | smiles = CC(N(C)C)CC1=CC=CC=C1 | StdInChI_Ref = | StdInChI = 1S/C11H17N/c1-10(12(2)3)9-11-7-5-4-6-8-11/h4-8,10H,9H2,1-3H3 | StdInChIKey_Ref = | StdInChIKey = OBDSVYOSYSKVMX-UHFFFAOYSA-N

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 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 of dextroamphetamine if the reaction temperature is too high or an excess of methylating agent is used.

It is said to be a prodrug of methamphetamine and amphetamine, which are minor metabolites.

References

References

1. (May 1990). "Behavioral effects of N-methylamphetamine and N,N-dimethylamphetamine in rats and squirrel monkeys". The Journal of Pharmacology and Experimental Therapeutics.
2. (June 1989). "Evaluation of the neurotoxic potential of N,N-dimethylamphetamine: an illicit analog of methamphetamine". Brain Research.
3. (October 1997). "N-methylation dissociates methamphetamine's neurotoxic and behavioral pharmacologic effects". Brain Research.
4. (1992). "Reinforcing effects of enantiomers of N,N-dimethylamphetamine in squirrel monkeys". Psychopharmacology.
5. "Microgram Bulletin". US Drug Enforcement Administration.
6. "The Identification of d-N,N-Dimethylamphetamine (DMA) in an Exhibit in Malaysia". US Drug Enforcement Administration.
7. (9 October 2013). "Forensic Medicine: Fundamentals and Perspectives". Springer Science & Business Media.
8. (May 2002). "Precursor medications as a source of methamphetamine and/or amphetamine positive drug testing results". J Occup Environ Med.
9. (August 1987). "The metabolism of dimethylamphetamine in rat and man". Xenobiotica.

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