Metamfepramone

Metamfepramone
Clinical data
Other names	Dimepropion; Dimethylcathinone; Dimethylpropion; N,N-Dimethyl-cathinone;
ATC code	none;
Legal status
Legal status	I-P(Poland);
Identifiers
	IUPAC name (RS)-2-dimethylamino-1-phenylpropan-1-one;
CAS Number	15351-09-4 ;
PubChem CID	71872;
ChemSpider	64889 ;
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 ; Key:KBHMHROOFHVLBA-UHFFFAOYSA-N ;
	(what is this?) (verify)

Metamfepramone (INN; also known as dimepropion (BAN), dimethylcathinone, and dimethylpropion) 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 is considered a Schedule I controlled substance as a positional isomer of mephedrone.^[6]

References

^ "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.
^ Soholing WE (February 1982). "[Therapy of the orthostatic syndrome. Studies using dimepropion-HCI]". Fortschritte der Medizin (in German). 100 (7): 289–293. PMID 7042502.
^ Siegel-Itzkovich J (22 February 2006). "Recreational drug 'rakefet' banned". The Jerusalem Post.
^ 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.
^ 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.
^ "Orange Book - List of Controlled Substances and Regulated Chemicals" (PDF). Drug Enforcement Administration. Archived (PDF) from the original on 6 March 2023.

[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.

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[2]

[3]

[4]

[5]

[6]

v t e Stimulants
Adamantanes	Adapromine Amantadine Bromantane Memantine Rimantadine
Adenosine antagonists	8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Istradefylline Paraxanthine SCH-58261 Theobromine Theophylline
Alkylamines	Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane
Ampakines	CX-516 CX-546 CX-614 CX-691 CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org 26576 PEPA S-18986 Sunifiram Unifiram
Arylcyclohexylamines	Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine
Benzazepines	6-Br-APB SKF-77434 SKF-81297 SKF-82958
Cathinones	3-FMC 3-MMC 3,4-DMMC 4-BMC 4-CMC 4-Methylbuphedrone 4-Methylcathinone 4-MEAP 4-Methylpentedrone Amfepramone Benzedrone Buphedrone Bupropion Butylone Cathinone Dimethylcathinone Ethcathinone Ethylone Flephedrone Hexedrone Isoethcathinone Mephedrone Methcathinone Methedrone Methylenedioxycathinone Methylone Mexedrone N-Ethylbuphedrone N-Ethylhexedrone Pentedrone Pentylone Phthalimidopropiophenone
Cholinergics	A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 Tebanicline UB-165 Varenicline WAY-317,538
Convulsants	Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone
Eugeroics	Adrafinil Armodafinil CRL-40,940 CRL-40,941 Fluorenol Modafinil
Oxazolines	4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fluoroamphetamine 2-Fluoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fluoroamphetamine 3-Fluoroethamphetamine 3-Methoxyamphetamine 3-Methylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-MMA 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Camfetamine Cathine Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethylnorepinephrine Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine Fludorex 4-Fluorodeprenyl Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methoxyphenamine MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Prenylamine Propylamphetamine Pseudoephedrine Pyr-AI Ropinirole Salbutamol (Levosalbutamol) Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine
Phenylmorpholines	3-Fluorophenmetrazine Fenbutrazate Fenmetramide G-130 Manifaxine Morazone Morforex Oxaflozane PD-128,907 Phendimetrazine Phenmetrazine 2-Phenyl-3,6-dimethylmorpholine Pseudophenmetrazine Radafaxine
Piperazines	2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 JJC8-088 MeOPP MBZP oMPP Vanoxerine
Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate JZ-IV-10 Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate Serdexmethylphenidate SCH-5472
Phenethylpyrrolidines	2-Diphenylmethylpyrrolidine 4-Cl-PVP 5-DBFPV α-PPP α-PBP α-PCYP α-PHiP α-PHP α-PHPP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPEP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone
Racetams	Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide
Psychedelics	2,5-DMA (DOH) 2C-B 2C-D 2C-G-N 5-MeO-DiPT 5-MeO-MiPT Ariadne (4C-DOM; BL-3912; Dimoxamine) ASR-2001 (2CB-5PrO) DOET DOM DON DOPR LSD MTFEM
Tropanes	4-fluorotropacocaine 4'-Fluorococaine Altropane (IACFT) Brasofensine CFT (WIN 35,428) β-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-β-CPPIT FP-β-CPPIT Ioflupane (¹²³I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (β-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33
Tryptamines	4-HO-αMT 4-Methyl-αET 4-Methyl-αMT 5-Chloro-αMT 5-Fluoro-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-DIPT 6-Fluoro-αMT 7-Methyl-αET αET αMT
Others	2-MDP 3,3-Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 Desipramine Diclofensine Dimethocaine Efaroxan Etamivan Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 Lazabemide Leptacline Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methamnetamine Methastyridone Methiopropamine Naphthylaminopropane Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline PNU-99,194 PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Thiopropamine Thiothinone Trazium UH-232 Yohimbine
ATC code: N06B

Clinical data

Other names	Dimepropion Dimethylcathinone Dimethylpropion N,N-Dimethyl-cathinone
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)

Epstein Files Full PDF

Legal status

See also

References