Metamfepramone

Metamfepramone

Clinical data
ATC code	none
Legal status
Legal status	I-P(Poland) [1]
Identifiers
IUPAC name (RS)-2-dimethylamino-1-phenylpropan-1-one
CAS Number	15351-09-4  Y
PubChem CID	71872
ChemSpider	64889  N
UNII	04A0P12FH2
CompTox Dashboard (EPA)	DTXSID7057650
ECHA InfoCard	100.035.788
Chemical and physical data
Formula	C11H15NO
Molar mass	177.247 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C(=O)C1=CC=CC=C1)N(C)C
InChI InChI=1S/C11H15NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9H,1-3H3 N Key:KBHMHROOFHVLBA-UHFFFAOYSA-N N
NY  (what is this?)    (verify)

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. ^[2]

It was used as a recreational drug in Israel under the name rakefet, but was made illegal in 2006. ^[3]

Metamfepramone is metabolized to produce N-methylpseudoephedrine and methcathinone. ^[4] It has also been found to be about 1.6 times less potent than methcathinone, making it roughly equipotent to cathinone itself. ^[5]

Legal status

In the United States, metamfepramone (N,N-Dimethyl-cathinone) is considered a Schedule I controlled substance as a positional isomer of mephedrone. ^[6]

See also

• Dimethylamphetamine
• Substituted cathinone

References

1. "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". Internetowy System Aktów Prawnych. Retrieved 17 June 2011.
2. Soholing WE (February 1982). "[Therapy of the orthostatic syndrome. Studies using dimepropion-HCI]". Fortschritte der Medizin (in German). 100 (7): 289–293. PMID   7042502.
3. Siegel-Itzkovich J (22 February 2006). "Recreational drug 'rakefet' banned". The Jerusalem Post.
4. Thevis M, Sigmund G, Thomas A, Gougoulidis V, Rodchenkov G, Schänzer W (2009). "Doping control analysis of metamfepramone and two major metabolites using liquid chromatography-tandem mass spectrometry". European Journal of Mass Spectrometry. 15 (4): 507–515. doi:10.1255/ejms.1010. PMID   19661559. S2CID   41715902.
5. Dal Cason TA, Young R, Glennon RA (December 1997). "Cathinone: an investigation of several N-alkyl and methylenedioxy-substituted analogs". Pharmacology, Biochemistry, and Behavior. 58 (4): 1109–1116. doi:10.1016/s0091-3057(97)00323-7. PMID   9408221. S2CID   9704972.
6. "Orange Book - List of Controlled Substances and Regulated Chemicals" (PDF). Drug Enforcement Administration . Archived (PDF) from the original on 6 March 2023.