Dimethylamphetamine

{{Short description|Chemical compound}} {{Drugbox | 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

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

| CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 4075-96-1 | ATC_prefix = none | ATC_suffix = | UNII_Ref= {{fdacite|correct|FDA}} | UNII= IYE3F3MHCU | PubChem = 20006 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 18847 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C22825

| C=11 | H=17 | N=1 | smiles = CC(N(C)C)CC1=CC=CC=C1 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C11H17N/c1-10(12(2)3)9-11-7-5-4-6-8-11/h4-8,10H,9H2,1-3H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | 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<ref name="pmid2338643">{{cite journal | vauthors = Witkin JM, Ricaurte GA, Katz JL | title = Behavioral effects of N-methylamphetamine and N,N-dimethylamphetamine in rats and squirrel monkeys | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 253 | issue = 2 | pages = 466–74 | date = May 1990 | pmid = 2338643 }}</ref> and less neurotoxic compared to methamphetamine.<ref name="pmid2765865">{{cite journal | vauthors = Ricaurte GA, DeLanney LE, Irwin I, Witkin JM, Katz JL, Langston JW | s2cid = 20682993 | title = Evaluation of the neurotoxic potential of N,N-dimethylamphetamine: an illicit analog of methamphetamine | journal = Brain Research | volume = 490 | issue = 2 | pages = 301–6 | date = June 1989 | pmid = 2765865 | doi = 10.1016/0006-8993(89)90247-3 }}</ref><ref name="pmid9383014">{{cite journal | vauthors = Fasciano J, Hatzidimitriou G, Yuan J, Katz JL, Ricaurte GA | title = N-methylation dissociates methamphetamine's neurotoxic and behavioral pharmacologic effects | journal = Brain Research | volume = 771 | issue = 1 | pages = 115–20 | date = October 1997 | pmid = 9383014 | doi = 10.1016/s0006-8993(97)00801-9 | s2cid = 8456534 | doi-access = free }}</ref> However, it still retains some mild stimulant effects and abuse potential,<ref name="pmid1615131">{{cite journal | vauthors = Katz JL, Ricaurte GA, Witkin JM | s2cid = 24707878 | title = Reinforcing effects of enantiomers of N,N-dimethylamphetamine in squirrel monkeys | journal = Psychopharmacology | volume = 107 | issue = 2–3 | pages = 315–8 | date = 1992 | pmid = 1615131 | doi = 10.1007/BF02245154 }}</ref> 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.<ref>{{cite web | url = http://www.justice.gov/dea/pr/micrograms/2005/mg0205.pdf | publisher = US Drug Enforcement Administration | title = Microgram Bulletin | access-date = 2013-08-06 | archive-date = 2013-04-14 | archive-url = https://web.archive.org/web/20130414122936/http://www.justice.gov/dea/pr/micrograms/2005/mg0205.pdf | url-status = dead }}</ref><ref>{{cite web | url = https://www.erowid.org/library/periodicals/microgram/microgram_journal_2003-2.pdf | publisher = US Drug Enforcement Administration | title = The Identification of d-N,N-Dimethylamphetamine (DMA) in an Exhibit in Malaysia }}</ref>

It is said to be a prodrug of methamphetamine and amphetamine, which are minor metabolites.<ref name="DettmeyerVerhoff2013">{{cite book| vauthors = Dettmeyer R, Verhoff MA, Schütz HF |title=Forensic Medicine: Fundamentals and Perspectives|url=https://books.google.com/books?id=yHHABAAAQBAJ&pg=PA519|date=9 October 2013|publisher=Springer Science & Business Media|isbn=978-3-642-38818-7|page=519 | quote = Table 30.13: Amphetamine Data [...] ''Note:'' So-called prodrugs, such as amphetaminil (psychoanaleptic), benzphetamine, clobenzorex, dimethylamphetamine, ethylamphetamine, famprofazone, fencamine, fenethylline, fenproporex, furfenorex, mefenorex, mesocarb, prenylamine, and selegiline (antiparkinson agent), can result in the production of methamphetamine or amphetamine in the organism}}</ref><ref name="Cody2002">{{cite journal | vauthors = Cody JT | title = Precursor medications as a source of methamphetamine and/or amphetamine positive drug testing results | journal = J Occup Environ Med | volume = 44 | issue = 5 | pages = 435–450 | date = May 2002 | pmid = 12024689 | doi = 10.1097/00043764-200205000-00012 | url = }}</ref><ref name="InoueSuzuki1987">{{cite journal | vauthors = Inoue T, Suzuki S | title = The metabolism of dimethylamphetamine in rat and man | journal = Xenobiotica | volume = 17 | issue = 8 | pages = 965–971 | date = August 1987 | pmid = 3673111 | doi = 10.3109/00498258709044195 | url = }}</ref>

==See also== * Substituted amphetamine

==References== {{Reflist}}

==External links== * [https://isomerdesign.com/pihkal/explore/2007 NNDMA (''N'',''N''-Dimethylamphetamine) - Isomer Design]

Category:Designer prodrugs Category:Dimethylamino compounds Category:Methamphetamines Category:Norepinephrine-dopamine releasing agents Category:Substituted amphetamines