Metamfepramone

{{Short description|Stimulant drug}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 447191591

| IUPAC_name = (RS)-2-dimethylamino-1-phenylpropan-1-one

| image = Dimethylcathinone.svg

| width = 200px

| tradename =

| legal_status = I-P(Poland){{cite web | title = Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 ) | url = http://isap.sejm.gov.pl/DetailsServlet?id=WDU20111050614 | publisher = Internetowy System Aktów Prawnych | access-date = 17 June 2011}}

| routes_of_administration =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 15351-09-4

| ATC_prefix = none

| PubChem = 71872

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 04A0P12FH2

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 64889

| C=11 | H=15 | N=1 | O=1

| smiles = CC(C(=O)C1=CC=CC=C1)N(C)C

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C11H15NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9H,1-3H3

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = KBHMHROOFHVLBA-UHFFFAOYSA-N

}}

Metamfepramone (INN, also known as dimethylcathinone, dimethylpropion, and dimepropion (BAN)) is a stimulant drug of the phenethylamine, and cathinone chemical classes. Dimethylcathinone was evaluated as an appetite suppressant and for the treatment of hypotension, but was never widely marketed.{{cite journal | vauthors = Soholing WE | title = [Therapy of the orthostatic syndrome. Studies using dimepropion-HCI] | language = German | journal = Fortschritte der Medizin | volume = 100 | issue = 7 | pages = 289–293 | date = February 1982 | pmid = 7042502 }}

It was used as a recreational drug in Israel under the name rakefet, but was made illegal in 2006.{{cite news | vauthors = Siegel-Itzkovich J |title=Recreational drug 'rakefet' banned |url=https://www.jpost.com/Health-and-Sci-Tech/Health/Recreational-drug-rakefet-banned |work=The Jerusalem Post |date=22 February 2006 }}

Metamfepramone is metabolized to produce N-methylpseudoephedrine and methcathinone.{{cite journal | vauthors = Thevis M, Sigmund G, Thomas A, Gougoulidis V, Rodchenkov G, Schänzer W | title = Doping control analysis of metamfepramone and two major metabolites using liquid chromatography-tandem mass spectrometry | journal = European Journal of Mass Spectrometry | volume = 15 | issue = 4 | pages = 507–515 | year = 2009 | pmid = 19661559 | doi = 10.1255/ejms.1010 | s2cid = 41715902 }} It has also been found to be about 1.6 times less potent than methcathinone, making it roughly equipotent to cathinone itself.{{cite journal | vauthors = Dal Cason TA, Young R, Glennon RA | title = Cathinone: an investigation of several N-alkyl and methylenedioxy-substituted analogs | journal = Pharmacology, Biochemistry, and Behavior | volume = 58 | issue = 4 | pages = 1109–1116 | date = December 1997 | pmid = 9408221 | doi = 10.1016/s0091-3057(97)00323-7 | s2cid = 9704972 }}

== Legal Status ==

In the United States, metamfepramone (N,N-Dimethyl-cathinone) is considered a Schedule I controlled substance as a positional isomer of mephedrone.{{cite web |url=https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf |title=Orange Book - List of Controlled Substances and Regulated Chemicals |website=Drug Enforcement Administration |archive-url=https://web.archive.org/web/20230306093455/https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf |archive-date=6 March 2023 |url-status=live}}