Dimethylamphetamine: Difference between revisions

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+{{Short description|Chemical compound}}
 {{Drugbox
+| Verifiedfields = changed
-| verifiedrevid = 448000158
+| Watchedfields = changed
+| verifiedrevid = 449577684
 | IUPAC_name = ''N'',''N''-dimethyl-1-phenylpropan-2-amine
 | image = Dimethylamphetamine.svg
+| image2 = Dimetamfetamin.png
-| width = 200
 <!--Clinical data-->
 | tradename =
 | pregnancy_category =
+| legal_AU = S9
-| legal_status = Schedule I
+| legal_US = Schedule I
 | routes_of_administration = Oral
@@ Line 15: / Line 19: @@
 | metabolism =
 | elimination_half-life =
 | excretion =
 <!--Identifiers-->
+| CAS_number_Ref = {{cascite|correct|CAS}}
 | CAS_number = 4075-96-1
 | ATC_prefix = none
 | ATC_suffix =
+| UNII_Ref= {{fdacite|correct|FDA}}
-| PubChem = 541869
+| UNII= IYE3F3MHCU
-| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
-| ChemSpiderID = 471861
+| PubChem = 20006
+| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
+| ChemSpiderID = 18847
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = C22825
 <!--Chemical data-->
 | C=11 | H=17 | N=1
+| smiles = CC(N(C)C)CC1=CC=CC=C1
-| molecular_weight = 163.259 g/mol
-| smiles = c1(cccc(c1C)CC(N)C)C
-| InChI = 1/C11H17N/c1-8-5-4-6-11(10(8)3)7-9(2)12/h4-6,9H,7,12H2,1-3H3
-| InChIKey = HOBBTQMIPDOWRL-UHFFFAOYAH
 | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
-| StdInChI = 1S/C11H17N/c1-8-5-4-6-11(10(8)3)7-9(2)12/h4-6,9H,7,12H2,1-3H3
+| 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 = HOBBTQMIPDOWRL-UHFFFAOYSA-N
+| StdInChIKey = OBDSVYOSYSKVMX-UHFFFAOYSA-N
 }}
-'''Dimethylamphetamine''' ('''Metrotonin'''), also referred to as '''dimetamfetamine''' and '''''N'',''N''-dimethylamphetamine''', is a [[stimulant]] [[drug]] of the [[substituted_phenethylamine|phenethylamine]] and [[substituted_amphetamine|amphetamine]] [[chemical class]]es. Dimethylamphetamine has weaker stimulant effects than [[amphetamine]] or [[methamphetamine]] and is considerably less addictive<ref>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.</ref> and less neurotoxic compared to methamphetamine.<ref>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.</ref><ref>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.</ref> However, it still retains some mild stimulant effects and abuse potential,<ref>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.</ref> and is a [[Schedule I]] controlled drug.
+'''Dimethylamphetamine''' ('''Metrotonin'''), also known as '''dimetamfetamine''' ([[International Nonproprietary Name|INN]]), '''dimephenopan''' and '''''N'',''N''-dimethylamphetamine''', is a [[stimulant]] [[drug]] of the [[substituted phenethylamine|phenethylamine]] and [[substituted amphetamine|amphetamine]] [[chemical class]]es. 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 a [[Controlled Substances Act#Schedule I controlled substances|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.<ref>[http://justice.gov/dea/programs/forensicsci/microgram/mg0205/mg0205.html US Drug Enforcement Administration: Microgram Bulletin]</ref><ref>[http://www.usdoj.gov/dea//programs/forensicsci/microgram/journal071203/mj071203_pg2.html US Drug Enforcement Administration: The Identification of d-N,N-Dimethylamphetamine (DMA) in an Exhibit in Malaysia]</ref>
+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.<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 = 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 }}</ref>
+It is said to be a [[prodrug]] of [[amphetamine]]/[[methamphetamine]].<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|pages=519–}}</ref>
-== References ==
-{{Reflist|2}}
+==References==
+{{Reflist|2}}
 {{Stimulants}}
+{{Monoamine releasing agents}}
-{{Adrenergics}}
-{{Dopaminergics}}
 {{Phenethylamines}}
-[[Category:Amphetamines]]
+[[Category:Norepinephrine-dopamine releasing agents]]
+[[Category:Prodrugs]]
+[[Category:Substituted amphetamines]]
+[[Category:Dimethylamino compounds]]