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

| 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 = {{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{{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 }} and less neurotoxic compared to methamphetamine.{{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 }}{{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 }} However, it still retains some mild stimulant effects and abuse potential,{{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 }} 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.{{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 }}{{cite web | url = http://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 }}

It is said to be a prodrug of amphetamine/methamphetamine.{{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|pages=519–}}