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Metamfepramone

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(Redirected from Dimethylcathinone) Stimulant drug Pharmaceutical compound
Metamfepramone
Clinical data
ATC code
  • none
Legal status
Legal status
  • I-P(Poland)
Identifiers
IUPAC name
  • (RS)-2-dimethylamino-1-phenylpropan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.035.788 Edit this at Wikidata
Chemical and physical data
FormulaC11H15NO
Molar mass177.247 g·mol
3D model (JSmol)
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
  • Key:KBHMHROOFHVLBA-UHFFFAOYSA-N
  (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.

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

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

Legal Status

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

See also

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). "". 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.
Stimulants
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ATC code: N06B
Monoamine releasing agents
DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
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See also: Receptor/signaling modulatorsMonoamine reuptake inhibitorsAdrenergicsDopaminergicsSerotonergicsMonoamine metabolism modulatorsMonoamine neurotoxins
Phenethylamines
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
Phenylalkylpyrrolidines
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(and close relatives)
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