Fenmetramide

Fenmetramide

Systematic (IUPAC) name
2-phenyl-3-methyl-morpholin-5-one
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	5588-29-4
ATC code	None
PubChem	CID 21789
ChemSpider	20479
UNII	WCH9HW127L^Y
KEGG	D04153
Chemical data
Formula	C₁₁H₁₃N O₂
Mol. mass	191.23 g/mol
SMILES	eMolecules & PubChem

Fenmetramide is a drug which was patented as an antidepressant by McNeil in the 1960s.^[1] The drug was never marketed.^[2] It is the 5-ketone derivative of phenmetrazine and would similarly be expected to produce psychostimulant effects, though pharmacological data is lacking.

References [link]

^ US Patent 3308121 - 3-MORPHOLINONES, THIONES & 5,6 OXAZINES
^ David J. Triggle (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 0-412-46630-9. https://books.google.com/books?id=A0THacd46ZsC&lpg=PA1333&dq=fenmetramide&pg=PA1333#v=onepage&q=fenmetramide&f=false.

Antidepressants (N06A)

Specific reuptake inhibitors (RIs), enhancers (REs), and releasing agents (RAs)

Selective serotonin reuptake inhibitors (SSRIs)	Alaproclate Citalopram Escitalopram Femoxetine Fluoxetine^# Fluvoxamine Indalpine Ifoxetine Litoxetine Lubazodone Omiloxetine Panuramine Paroxetine Pirandamine Seproxetine Sertraline^# Zimelidine^‡

Serotonin–norepinephrine reuptake inhibitors (SNRIs)	Clovoxamine Desvenlafaxine Duloxetine Levomilnacipran Eclanamine Milnacipran Sibutramine Venlafaxine

Serotonin–norepinephrine–dopamine reuptake inhibitors (SNDRIs)	Amitifadine Bicifadine Brasofensine BTS-74,398 Cocaine Diclofensine DOV-21,947 DOV-102,677 DOV-216,303 EXP-561 Fezolamine JNJ-7925476 NS-2359 PRC200-SS Pridefine SEP-225,289 SEP-227,162 Tesofensine

Norepinephrine reuptake inhibitors (NRIs)	Amedalin Atomoxetine/Tomoxetine Binedaline Ciclazindol Daledalin Edivoxetine Esreboxetine Lortalamine Mazindol Nisoxetine Reboxetine Talopram Talsupram Tandamine Viloxazine

Dopamine reuptake inhibitors (DRIs)	Medifoxamine Vanoxerine

Norepinephrine-dopamine reuptake inhibitors (NDRIs)	Amineptine Bupropion/Amfebutamone^# Cilobamine Manifaxine Methylphenidate Nomifensine Radafaxine Tametraline

Norepinephrine-dopamine releasing agents (NDRAs)	Amphetamine Befuraline Lisdexamfetamine Methamphetamine Phenethylamine Piberaline Tranylcypromine

Serotonin-norepinephrine-dopamine releasing agents (SNDRAs)	4-Methyl-αMT αET/Etryptamine αMT/Metryptamine

Selective serotonin reuptake enhancers (SSREs)	Tianeptine

Others	Indeloxazine Teniloxazine Tramadol Viqualine

Receptor antagonists and/or reuptake inhibitors

Serotonin antagonists and reuptake inhibitors (SARIs)	Etoperidone Nefazodone Trazodone

Noradrenergic and specific serotonergic antidepressants (NaSSAs)	Aptazapine Esmirtazapine Mianserin Mirtazapine Setiptiline/Teciptiline

Norepinephrine-dopamine disinhibitors (NDDIs)	Agomelatine

Serotonin modulators and stimulators (SMSs)	Vortioxetine

Others	Tedatioxetine Vilazodone

Heterocyclic antidepressants (bi-, tri-, and tetracyclics)

Bicyclics	Tiazesim Tofenacin

Tricyclics	Amezepine Amineptine Amitriptyline^# Amitriptylinoxide Azepindole Butriptyline Cianopramine Clomipramine Cotriptyline Cyanodothiepin Demexiptiline Depramine/Balipramine Desipramine Dibenzepin Dimetacrine Dosulepin/Dothiepin Doxepin Enprazepine Fluotracen Hepzidine Homopipramol Imipramine Imipraminoxide Intriptyline Iprindole Ketipramine Litracen Lofepramine Losindole Mariptiline Melitracen Metapramine Mezepine Naranol Nitroxazepine Nortriptyline Noxiptiline Octriptyline Opipramol Pipofezine Propizepine Protriptyline Quinupramine Tampramine Tianeptine Tienopramine Trimipramine

Tetracyclics	Amoxapine Aptazapine Azipramine Ciclazindol Ciclopramine Esmirtazapine Maprotiline Mazindol Mianserin Mirtazapine Oxaprotiline Setiptiline/Teciptiline

Monoamine oxidase inhibitors (MAOIs)

Nonselective	Irreversible: Benmoxin Carbenzide Cimemoxin Domoxin Echinopsidine Iproclozide Iproniazid Isocarboxazid Mebanazine Metfendrazine Nialamide Octamoxin Phenelzine Pheniprazine Phenoxypropazine Pivalylbenzhydrazine Safrazine Tranylcypromine Reversible: Caroxazone Paraxazone Quercetin

MAO_A-Selective	Irreversible: Clorgiline Reversible: Amiflamine Bazinaprine Befloxatone Befol Berberine Brofaromine Cimoxatone Esuprone Harmala Alkaloids (Harmine Harmaline Tetrahydroharmine Harman Norharman, etc) Methylene Blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone Tyrima

MAO_B-Selective	Irreversible: Ladostigil Mofegiline Pargyline Rasagiline Selegiline Reversible: Lazabemide Milacemide

Azapirones and other 5-HT_1A receptor agonists

Alnespirone Aripiprazole Befiradol Buspirone Eptapirone Flesinoxan Flibanserin Gepirone Ipsapirone Oxaflozane Tandospirone Vilazodone Zalospirone

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: PSO/PSI

mepr

dsrd (o, p, m, p, a, d, s), sysi/epon, spvo

proc(eval/thrp), drug(N5A/5B/5C/6A/6B/6D)

v t e Stimulants (N06B)

Adamantanes	Adaphenoxate Adapromine Amantadine Bromantane Chlodantane Gludantane Memantine Midantane

Adenosine antagonists	8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Paraxanthine SCH-58261 Theobromine Theophylline

Alkylamines	Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane

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 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 TC-5619 Tebanicline UB-165 Varenicline WAY-317,538

Convulsants	Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone

Eugeroics	Adrafinil Armodafinil CRL-40941 Modafinil

Oxazolines	4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone

Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Phenyl-2-(piperidin-1-yl)pentan-3-one 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fluoroamphetamine 2-Fluoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2-Phenyl-3-methylaminobutane 2,3-MDA 3-Fluoroamphetamine 3-Fluoroethamphetamine 3-Fluoromethcathinone 3-Methoxyamphetamine 3-Methylamphetamine 3,4-DMMC 4-BMC 4-Ethylamphetamine 4-FA 4-FMA 4-MA 4-MMA 4-MTA 6-FNE Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amfepramone Amidephrine Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine ß-Methylphenethylamine ß-Phenylmethamphetamine Benfluorex Benzedrone Benzphetamine BDB BOH BPAP Buphedrone Bupropion Butylone Cathine Cathinone Chlorphentermine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethcathinone Ethylamphetamine Ethylnorepinephrine Ethylone Etilefrine Famprofazone Fenbutrazate Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenmetramide Fenproporex Flephedrone Fludorex Furfenorex Gepefrine Hexapradol HMMA Hordenine Hydroxyamphetamine Ibopamine IMP Indanylamphetamine Iofetamine Isoetarine Isoethcathinone Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine Manifaxine MBDB MDA MDBU MDEA MDMA MDMPEA MDOH MDPR MDPEA Mefenorex Mephedrone Mephentermine Metanephrine Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methcathinone Methedrone Methoxyphenamine Methylone MMDA MMDMA MMMA Morazone N-Benzyl-1-phenethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxilofrine PBA PCA PHA Pargyline Pentorex Pentylone Phenatine Phendimetrazine Phenmetrazine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Prenylamine Propylamphetamine Pseudoephedrine Pseudophenmetrazine Radafaxine Ropinirole Salbutamol (Levosalbutamol) Sibutramine Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xamoterol Xylopropamine Zylofuramine

Piperazines	2C-B-BZP 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 1-(3,4-Dichlorophenyl)-1-(piperidin-2-yl)butane 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylphenidate Methylnaphthidate Methylphenidate (Dexmethylphenidate) N-Methyl-3ß-propyl-4ß-(4-chlorophenyl)piperidine Nocaine Phacetoperane Pipradrol SCH-5472

Pyrrolidines	2-Diphenylmethylpyrrolidine a-PPP a-PBP a-PVP Diphenylprolinol MDPPP MDPBP MDPV MPBP MPHP MPPP MOPPP Naphyrone PEP Prolintane Pyrovalerone

Tropanes	3-CPMT 3'-Chloro-3a-(diphenylmethoxy)tropane 3-Pseudotropyl-4-fluorobenzoate 4'-Fluorococaine AHN-1055 Altropane (IACFT) Brasofensine CFT (WIN 35,428) ß-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-ß-CPPIT FP-ß-CPPIT Ioflupane (¹²³I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-105 RTI-112 RTI-113 RTI-117 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-154 RTI-171 RTI-177 RTI-183 RTI-193 RTI-194 RTI-199 RTI-202 RTI-204 RTI-229 RTI-241 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (ß-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33 WF-60

Others	1-(Thiophen-2-yl)-2-aminopropane 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 2-Aminotetralin 2-MDP 2-Phenylcyclohexylamine 2-Phenyl-3,6-dimethylmorpholine 3-Benzhydrylmorpholine 3,3-Diphenylcyclobutanamine 5-(2-Aminopropyl)indole 5-Iodo-2-aminoindane AL-1095 Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Camfetamine Carphedon Ciclazindol Cilobamine Clofenciclan Cropropamide Crotetamide Cypenamine D-161 Diclofensine Dimethocaine Efaroxan Etamivan EXP-561 Fencamfamine Fenpentadiol Feprosidnine G-130 Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 JZ-IV-10 Lazabemide Leptacline Levopropylhexedrine Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Mesocarb Methastyridone Methiopropamine N-Methyl-3-phenylnorbornan-2-amine Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline Phthalimidopropiophenone PNU-99,194 Propylhexedrine PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Trazium UH-232 Yohimbine

See also Sympathomimetic amines

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