4-Ethylmethcathinone

4-ethylmethcathinone
Legal status

Legal status	DE: Anlage I (Authorized scientific use only) UK: Class B
Identifiers
IUPAC name 1-(4-ethylphenyl)-2-(methylamino)propan-1-one
CAS Number	1225622-14-9
ChemSpider	25630253
UNII	3I378P59DJ
Chemical and physical data
Formula	C₁₂H₁₇NO
Molar mass	191.27 g/mol
3D model (JSmol)	Interactive image
SMILES C(C(C)NC)(=O)C1=CC=C(C=C1)CC
InChI InChI=1S/C12H17NO/c1-4-10-5-7-11(8-6-10)12(14)9(2)13-3/h5-9,13H,4H2,1-3H3 Key:FUYPDKFWOHBUFT-UHFFFAOYSA-N

4-Ethylmethcathinone (4-EMC) is a recreational designer drug of the stimulant and entactogen class. It is a structural isomer of 4-MEC.

Legal status

4-Ethylmethcathinone is a controlled substance in the US state of Vermont as of January 2016.^[1] It is also covered by analogue provisions in many other jurisdictions.

References

↑ "Regulated Drugs Rule" (PDF). Vermont Department of Health. Retrieved 14 October 2015.

Empathogens/entactogens
Phenylalkyl- amines (other than cathinones)	Unfused benzene ring: 4-CAB 4-FA 4-FMA 4-MTA 4,4'-DMAR Ariadne Metaescaline MMA PMA PMEA PMMA Benzodioxine: EDMA Benzodioxoles: Phenethylamine: { Lophophine } Amphetamines: { 2-Methyl-MDA 2,3-MDA 3,4-MDA 5-Methyl-MDA 6-Methyl-MDA DiFMDA DMMDA DMMDA-2 EIDA MDEA MDMA MDMOH MDOH MMDA MMDA-2 MMDMA } 1-Phenylbutan-2-amines: { BDB EBDB MBDB } Phentermines: { MDMP MDPH } Benzofurans and dihidrobenzofurans: 5-APB 5-APDB 5-EAPB 5-MAPB 5-MAPDB 5-MBPB 6-APB 6-APDB 6-EAPB 6-MAPB 6-MAPDB Indanes: 5-APDI 5-MAPDI Indole: 6-API Naphtalenes: Methamnetamine Naphthylaminopropane Tetralin: 6-APT
Cyclized phenyl- alkylamines	Aminoindanes: 5-IAI AMMI ETAI MDAI MDMAI MMAI NM-2-AI TAI Aminotetralins: 6-CAT MDAT MDMAT
Cathinones	3-MMC 4-EMC Brephedrone Butylone Ethylone Eutylone Flephedrone Mephedrone Methedrone Methylone Pentylone
Tryptamines	4-Methyl-αET αET αMT
Chemical classes	Substituted amphetamine Sub. benzofuran Sub. cathinone Sub. MDPEA Sub. PEA Sub. tryptamine

Stimulants (category)
Adamantanes	Adapromine Amantadine Bromantane Memantine Rimantadine
Adenosine antagonists	8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Paraxanthine SCH-58261 Theobromine Theophylline
Alkylamines	Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Levopropylhexedrine 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
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 JZ-IV-10 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-Fuoroamphetamine 2-Fuoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fuoroamphetamine 3-Fluoroethamphetamine 3-Fluoromethcathinone 3-Methoxyamphetamine 3-Methylamphetamine 3,4-DMMC 4-BMC 4-CMC 4-Ethylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-Methylbuphedrone 4-Methylcathinone 4-MMA 4-Methylpentedrone 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amfepramone 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 Benzedrone Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Buphedrone Bupropion Butylone Camfetamine Cathine Cathinone Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethcathinone Ethylnorepinephrine Ethylone Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine Flephedrone Fludorex Formetorex Furfenorex Gepefrine Hexapradol Hexedrone HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine IMP Indanylamphetamine Iofetamine Isoetarine Isoethcathinone Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA MDBU MDEA MDMA MDMPEA MDOH MDPR MDPEA Mefenorex Mephedrone Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methcathinone Methedrone Methoxyphenamine Methylenedioxycathinone Methylone Mexedrone MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N-Ethylbuphedrone N-Ethylhexedrone N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine (drug) Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Pentedrone Pentylone Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Phthalimidopropiophenone Prenylamine Propylamphetamine Pseudoephedrine Ropinirole Salbutamol (Levosalbutamol) Sibutramine 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 MeOPP MBZP 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 Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate SCH-5472
Pyrrolidines	2-Diphenylmethylpyrrolidine 5-DBFPV α-PPP α-PBP α-PHP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone
Racetams	Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide
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 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

Adrenergic receptor modulators

α₁

Agonists: 6-FNE; Amidephrine; Anisodine; Buspirone; Cirazoline; Corbadrine; Desglymidodrine; Dexisometheptene; Dipivefrine; Dopamine; Droxidopa (L-DOPS); Ephedrine; Epinephrine; Etilefrine; Etilevodopa; Ethylnorepinephrine; Indanidine; Isometheptene; L-DOPA (levodopa); L-Phenylalanine; L-Tyrosine; Melevodopa; Metaraminol; Methoxamine; Methyldopa; Midodrine; Naphazoline; Norepinephrine; Octopamine (drug); Oxymetazoline; Phenylephrine; Phenylpropanolamine; Pseudoephedrine; Synephrine; Tetryzoline; Tiamenidine; XP21279; Xylometazoline

Antagonists: Abanoquil; Adimolol; Ajmalicine; Alfuzosin; Amosulalol; Anisodamine; Arotinolol; Atiprosin; Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine, risperidone); Benoxathian; Buflomedil; Bunazosin; Carvedilol; Corynanthine; Dapiprazole; Domesticine; Doxazosin; Ergolines (e.g., ergotamine, dihydroergotamine, lisuride, terguride); Etoperidone; Eugenodilol; Fenspiride; Hydroxyzine; Indoramin; Ketanserin; L-765,314; Labetalol; mCPP; Mepiprazole; Metazosin; Monatepil; Moxisylyte; Naftopidil; Nantenine; Nefazodone; Neldazosin; Niaprazine; Nicergoline; Niguldipine; Pardoprunox; Pelanserin; Phendioxan; Phenoxybenzamine; Phentolamine; Piperoxan; Prazosin; Quinazosin; Ritanserin; Silodosin; Spiperone; Talipexole; Tamsulosin; Terazosin; Tiodazosin; Tolazoline; Trazodone; Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin); Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, imipramine, trimipramine); Trimazosin; Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine); Urapidil; WB-4101; Zolertine

α₂

Agonists: (R)-3-Nitrobiphenyline; 4-NEMD; 6-FNE; Amitraz; Apraclonidine; Brimonidine; Cannabivarin; Clonidine; Corbadrine; Detomidine; Dexmedetomidine; Dihydroergotamine; Dipivefrine; Dopamine; Droxidopa (L-DOPS); Etilevodopa; Ephedrine; Ergotamine; Epinephrine; Etilefrine; Ethylnorepinephrine; Guanabenz; Guanfacine; Guanoxabenz; L-DOPA (levodopa); L-Phenylalanine; L-Tyrosine; Lofexidine; Medetomidine; Melevodopa; Methyldopa; Mivazerol; Naphazoline; Norepinephrine; Oxymetazoline; Phenylpropanolamine; Piperoxan; Pseudoephedrine; Rezatomidine; Rilmenidine; Romifidine; Talipexole; Tetrahydrozoline; Tiamenidine; Tizanidine; Tolonidine; Urapidil; XP21279; Xylazine; Xylometazoline

Antagonists: 1-PP; Adimolol; Aptazapine; Atipamezole; Atypical antipsychotics (e.g., asenapine, clozapine, lurasidone, paliperidone, quetiapine, risperidone, zotepine); Azapirones (e.g., buspirone, tandospirone); BRL-44408; Buflomedil; Cirazoline; Efaroxan; Esmirtazapine; Fenmetozole; Fluparoxan; Idazoxan; mCPP; Mianserin; Mirtazapine; NAN-190; Olanzapine; Pardoprunox; Phentolamine; Phenoxybenzamine; Piperoxan; Piribedil; Rauwolscine; Rotigotine; SB-269970; Setiptiline; Spiroxatrine; Sunepitron; Tolazoline; Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine); Yohimbine

Agonists: Abediterol; Alifedrine; Amibegron; Arbutamine; Arformoterol; Arotinolol; BAAM; Bambuterol; Befunolol; Bitolterol; Broxaterol; Buphenine; Carbuterol; Carmoterol; Cimaterol; Clenbuterol; Corbadrine; Denopamine; Dipivefrine; Dobutamine; Dopamine; Dopexamine; Droxidopa (L-DOPS); Ephedrine; Epinephrine; Etafedrine; Etilefrine; Etilevodopa; Ethylnorepinephrine; Fenoterol; Formoterol; Hexoprenaline; Higenamine; Indacaterol; Isoetarine; Isoprenaline; Isoxsuprine; L-DOPA (levodopa); L-Phenylalanine; L-Tyrosine; Levosalbutamol; Mabuterol; Melevodopa; Methoxyphenamine; Methyldopa; Mirabegron; Norepinephrine; Orciprenaline; Oxyfedrine; PF-610355; Phenylpropanolamine; Pirbuterol; Prenalterol; Ractopamine; Procaterol; Pseudoephedrine; Reproterol; Rimiterol; Ritodrine; Salbutamol; Salmeterol; Solabegron; Terbutaline; Tretoquinol; Tulobuterol; Vilanterol; Xamoterol; XP21279; Zilpaterol; Zinterol

Antagonists: Acebutolol; Adaprolol; Adimolol; Afurolol; Alprenolol; Alprenoxime; Amosulalol; Ancarolol; Arnolol; Arotinolol; Atenolol; Befunolol; Betaxolol; Bevantolol; Bisoprolol; Bopindolol; Bornaprolol; Brefonalol; Bucindolol; Bucumolol; Bufetolol; Bufuralol; Bunitrolol; Bunolol; Bupranolol; Butaxamine; Butidrine; Butofilolol; Capsinolol; Carazolol; Carpindolol; Carteolol; Carvedilol; Celiprolol; Cetamolol; Cicloprolol; Cinamolol; Cloranolol; Cyanopindolol; Dalbraminol; Dexpropranolol; Diacetolol; Dichloroisoprenaline; Dihydroalprenolol; Dilevalol; Diprafenone; Draquinolol; Ecastolol; Epanolol; Ericolol; Ersentilide; Esatenolol; Esprolol; Eugenodilol; Exaprolol; Falintolol; Flestolol; Flusoxolol; Hydroxycarteolol; Hydroxytertatolol; ICI-118,551; Idropranolol; Indenolol; Indopanolol; Iodocyanopindolol; Iprocrolol; Isoxaprolol; Isamoltane; Labetalol; Landiolol; Levobetaxolol; Levobunolol; Levomoprolol; Medroxalol; Mepindolol; Metipranolol; Metoprolol; Moprolol; Nadolol; Nadoxolol; Nebivolol; Nifenalol; Nipradilol; Oxprenolol; Pacrinolol; Pafenolol; Pamatolol; Pargolol; Penbutolol; Pindolol; Practolol; Primidolol; Procinolol; Pronethalol; Propafenone; Propranolol; Ridazolol; Ronactolol; Soquinolol; Sotalol; Spirendolol; SR 59230A; Sulfinalol; Talinolol; Tazolol; Tertatolol; Tienoxolol; Tilisolol; Timolol; Tiprenolol; Tolamolol; Toliprolol; Xibenolol; Xipranolol

See also: Receptor/signaling modulators

Dopaminergics

Serotonergics

Monoamine reuptake inhibitors

Monoamine releasing agents

Monoamine metabolism modulators

Monoamine neurotoxins

Dopamine receptor modulators

D₁-like

Agonists

Benzazepines 6-Br-APB Fenoldopam SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959 Trepipam Zelandopam
Ergolines Cabergoline CY-208,243 Dihydroergocryptine LEK-8829 Lisuride Pergolide Terguride
Dihydrexidine derivatives A-77636 A-86929 Adrogolide (ABT-431, DAS-431) Dihydrexidine Dinapsoline Dinoxyline Doxanthrine
Phenethylamines BCO-001 Deoxyepinephrine (N-methyldopamine, epinine) Dopexamine Etilevodopa Ibopamine L-DOPA (levodopa) Melevodopa L-Phenylalanine L-Tyrosine XP21279
Others A-68930 Apomorphine Isocorypalmine Nuciferine PF-6649751 PF 6669571 Propylnorapomorphine Rotigotine SKF-89,145 SKF-89,626 Stepholidine Tetrahydropalmatine

Antagonists

Typical antipsychotics Butaclamol Chlorpromazine Chlorprothixene Flupentixol (flupenthixol) (+melitracen) Fluphenazine Loxapine Perphenazine (+amitriptyline) Pifluthixol Thioridazine Thiothixene Trifluoperazine (+tranylcypromine) Zuclopenthixol
Atypical antipsychotics Asenapine Clorotepine Clotiapine Clozapine DHA-clozapine Fluperlapine Iloperidone Norclozapine Norquetiapine Olanzapine (++fluoxetine) Paliperidone Quetiapine Risperidone Tefludazine Zicronapine Ziprasidone Zotepine
Others Berupipam Ecopipam EEDQ Metitepine (methiothepin) Odapipam SCH-23390

D₂-like