Amfecloral

Amfecloral
Systematic (IUPAC) name

2,2,2-trichloro-N-(1-phenylpropan-2-yl)ethanimine
Clinical data
Legal status	?
Identifiers
CAS number	^Y
ATC code	None
PubChem
ChemSpider	^Y
UNII	^Y
KEGG	^Y
ChEMBL
Synonyms	alpha-methyl-N-(2,2,2-trichloroethylidene)phenethylamine; N-(2,2,2-trichloroethylidene)amphetamine
Chemical data
Formula	C₁₁H₁₂Cl₃N
Mol. mass	264.58 g/mol
SMILES ClC(Cl)(Cl)/C=N/C(Cc1ccccc1)C
InChI InChI=1S/C11H12Cl3N/c1-9(15-8-11(12,13)14)7-10-5-3-2-4-6-10/h2-6,8-9H,7H2,1H3/b15-8+^Y Key:VBZDETYCYXPOAK-OVCLIPMQSA-N^Y
Y

Amfecloral (INN), also known as amphecloral (USAN), is a stimulant drug of the phenethylamine and amphetamine chemical classes that was used as an appetite suppressant under the trade name Acutran, but is now no longer marketed.^[1] It acts as a prodrug which splits to form amphetamine and chloral hydrate, similarly to clobenzorex and related compounds, except that the N-substituent in this case yields a compound that is active in its own right. The chloral hydrate metabolite is a gabaminergic sedative/hypnotic, and would in theory counteract some of the stimulant effects of the amphetamine metabolite. This would produce an effect similar to the amphetamine/barbiturate combinations previously used in psychiatric medications.

Synthesis

Amphetamine + Chloral hydrate → 1-phenyl-N-(2,2,2-trichloroethylidene)propan-2-amine.

C. Cavallito, U.S. Patent 2,923,661 (1960);
Chem. Abstr., 54: 9846c (1966).

References

^ Ganellin, C. R.; Triggle, David J. (1996). Dictionary of pharmacological agents, Volumes 1-2. Chapman & Hall. p. 67.

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

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-40,941 Fluorenol JZ-IV-10 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 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 Fencamfamine Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine Flephedrone Fludorex Formetorex Furfenorex Gepefrine Hexapradol 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 Methylone MMDA MMDMA MMMA Morforex N-Benzyl-1-phenethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PHA Pentorex 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

Phenmetrazines	Fenbutrazate Fenmetramide G-130 Manifaxine Morazone Morforex Oxaflozane PD-128,907 Phendimetrazine Phenmetrazine 2-Phenyl-3,6-dimethylmorpholine Pseudophenmetrazine Radafaxine

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-3β-propyl-4β-(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 Picilorex Prolintane Pyrovalerone

Tropanes	3-CPMT 3'-Chloro-3a-(diphenylmethoxy)tropane 4-fluorotropacocaine 4'-Fluorococaine AHN-1055 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-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 (β-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33 WF-60

Racetams	Oxiracetam Phenylpiracetam

Others	2-MDP 2-Phenylcyclohexylamine 3,3-Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 Diclofensine Dimethocaine Efaroxan Etamivan EXP-561 Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 Lazabemide Leptacline Levopropylhexedrine Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methastyridone Methiopropamine N-Methyl-3-phenylnorbornan-2-amine Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline PNU-99,194 Propylhexedrine PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Thiopropamine Trazium UH-232 Yohimbine

Antiobesity agents/Anorectics (A08)

Central

Stimulants	4-Methylamphetamine^‡ Amfecloral Amfepentorex Amfepramone Aminorex Amphetamine Amphetaminil Atomoxetine Benfluorex^‡ Benzphetamine Bupropion (+naltrexone; +zonisamide^†) Cathine Cathinone Chlorphentermine Ciclazindol Clobenzorex Cloforex Clominorex Clortermine Dexfenfluramine^‡ Dextroamphetamine Dextromethamphetamine^‡ Dexmethylphenidate Difemetorex Dimethylcathinone Diphemethoxidine Ephedrine Ephedra^‡ Etilamfetamine Etolorex Fenbutrazate Fencamfamine Fenethylline Fenfluramine^‡ (+phentermine^‡) Fenproporex Fludorex Fluminorex Furfenorex Indanorex Khat Levopropylhexedrine Lisdexamfetamine Manifaxine Mazindol Mefenorex Methamphetamine Methylphenidate Norfenfluramine Pemoline Pentorex Phendimetrazine Phenethylamine Phenmetrazine Phentermine (+topiramate) Phenylpropanolamine Picilorex Pipradrol Prolintane Propylhexedrine Pseudoephedrine Pyrovalerone Radafaxine Reboxetine Setazindol Sibutramine^‡ Synephrine Tesofensine Viloxazine Xylopropamine Zylofuramine

Cannabinoids	Drinabant^§ • Ibipinabant^§ • Otenabant^§ • Rimonabant^‡ • Rosonabant^§ • Surinabant^§ • Taranabant^§

Others	5-HTP • Galactomannan (Guar gum) • Glucomannan • L-DOPA • L-Phenylalanine • L-Tryptophan • L-Tyrosine • Lorcaserin • Lu AA-33810 • Metformin • Naltrexone • Naloxone • Oxyntomodulin • P57 • Peptide YY • Topiramate • Yohimbine (Yohimbe) • Zonisamide • water

Peripheral

Cetilistat • 2,4-Dinitrophenol^‡ • Dirlotapide • Mitratapide • Oleoyl-estrone • Orlistat • Simmondsin • Sterculia

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

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drug (//)

Hypnotics/sedatives (N05C)

GABA_A
agonists/PAMs

Alcohols:	2M2B Chloralodol Ethanol Alcohol Ethchlorvynol Methylpentynol Trichloroethanol

Barbiturates:	Allobarbital Amobarbital Aprobarbital Barbital Butabarbital Butobarbital Cyclobarbital Ethallobarbital Heptabarb Hexobarbital Mephobarbital Methohexital Pentobarbital Phenallymal Phenobarbital Propylbarbital Proxibarbal Reposal Secobarbital Talbutal Thiamylal Thiopental Vinbarbital Vinylbital

Benzodiazepines:	Brotizolam Cinolazepam Climazolam Doxefazepam Estazolam Flunitrazepam Flurazepam Flutoprazepam Haloxazolam Loprazolam Lormetazepam Midazolam Nimetazepam Nitrazepam Quazepam Temazepam Triazolam

Carbamates:	Carisoprodol Emylcamate Ethinamate Hexapropymate Meprobamate Methocarbamol Phenprobamate Procymate Tybamate

Neuroactive Steroids:	Acebrochol Allopregnanolone Alphadolone Alphaxolone Eltanolone Ganaxolone Hydroxydione Minaxolone Org 20599 Org 21465 Tetrahydrodeoxycorticosterone

Nonbenzodiazepines:	CL-218,872 Eszopiclone Indiplon JM-1232 Lirequinil Necopidem Pazinaclone ROD-188 Saripidem Suproclone Suriclone SX-3228 U-89843A U-90042 Zaleplon Zolpidem Zopiclone

Phenols:	Fospropofol Propofol

Piperidinediones:	Glutethimide Methyprylon Pyrithyldione Piperidione

Quinazolinones:	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164

Volatiles/gases	Acetophenone Acetylglycinamide chloral hydrate Centalun Chloral hydrate Paraldehyde

Others:	Bromide Lithium bromide Potassium bromide Sodium bromide Chloralose Clomethiazole Dichloralphenazone Etomidate Gaboxadol Loreclezole Metomidate Org 25435 Petrichloral Sulfonmethane Triclofos Valerenic acid Valerian

GABA_B
agonists

H₁ inverse
agonists

Antihistamines:	Captodiame Cyproheptadine Diphenhydramine Doxylamine Hydroxyzine Methapyrilene Pheniramine Promethazine Propiomazine

Antidepressants	Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.

Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.

α₁-Adrenergic
antagonists

Antidepressants	Serotonin antagonists and reuptake inhibitors Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin

Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.

Others:	Niaprazine

α₂-Adrenergic
agonists

5-HT_2A
antagonists

Antidepressants	Serotonin antagonists and reuptake inhibitors Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.

Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.

Others:	Eplivanserin Niaprazine Pruvanserin Volinanserin

Melatonin
agonists

Orexin
antagonists

Others

Acecarbromal
Apronal
Bromisoval
Cannabidiol
- Cannabis
Carbromal
Diethylpropanediol
Embutramide
Evoxine
Fenadiazole
Gabapentin
Kavalactones
- Kava
Mephenoxalone
Metaglycodol
Opioids
- Oxycodone
- Morphine
  - Opium), etc.
Passion flower
Phenaglycodol
Scopolamine
- Mandrake
UMB68
Valnoctamide

Catecholaminergics

Adrenergics

Receptor ligands

α₁	Agonists: 5-FNE 6-FNE Amidephrine Anisodamine Anisodine Cirazoline Dipivefrine Dopamine Ephedrine Epinephrine Etilefrine Ethylnorepinephrine Indanidine Levonordefrin Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine Octopamine Oxymetazoline Phenylephrine Phenylpropanolamine Pseudoephedrine Synephrine Tetrahydrozoline Antagonists: Abanoquil Adimolol Ajmalicine Alfuzosin Amosulalol Arotinolol Atiprosin Benoxathian Buflomedil Bunazosin Carvedilol CI-926 Corynanthine Dapiprazole DL-017 Domesticine Doxazosin Eugenodilol Fenspiride GYKI-12,743 GYKI-16,084 Hydroxyzine Indoramin Ketanserin L-765,314 Labetalol Mephendioxan Metazosin Monatepil Moxisylyte Naftopidil Nantenine Neldazosin Nicergoline Niguldipine Pelanserin Phendioxan Phenoxybenzamine Phentolamine Piperoxan Prazosin Quinazosin Ritanserin RS-97,078 SGB-1,534 Silodosin SL-89.0591 Spiperone Talipexole Tamsulosin Terazosin Tibalosin Tiodazosin Tipentosin Tolazoline Trimazosin Upidosin Urapidil Zolertine * Note that many TCAs, TeCAs, antipsychotics, ergolines, and some piperazines like buspirone and trazodone all antagonize α₁-adrenergic receptors as well, which contributes to their side effects such as orthostatic hypotension.

α₂	Agonists: (R)-3-Nitrobiphenyline 4-NEMD 6-FNE Amitraz Apraclonidine Brimonidine Cannabivarin Clonidine Detomidine Dexmedetomidine Dihydroergotamine Dipivefrine Dopamine Ephedrine Ergotamine Epinephrine Esproquin Etilefrine Ethylnorepinephrine Guanabenz Guanfacine Guanoxabenz Levonordefrin Lofexidine Medetomidine Methyldopa Mivazerol Naphazoline Norepinephrine Oxymetazoline Phenylpropanolamine Piperoxan Pseudoephedrine Rilmenidine Romifidine Talipexole Tetrahydrozoline Tizanidine Tolonidine Urapidil Xylazine Xylometazoline Antagonists: 1-PP Adimolol Aptazapine Atipamezole BRL-44408 Buflomedil Cirazoline Efaroxan Esmirtazapine Fenmetozole Fluparoxan GYKI-12,743 GYKI-16,084 Idazoxan Mianserin Mirtazapine MK-912 NAN-190 Olanzapine Phentolamine Phenoxybenzamine Piperoxan Piribedil Rauwolscine Rotigotine SB-269,970 Setiptiline Spiroxatrine Sunepitron Tolazoline Yohimbine * Note that many atypical antipsychotics and azapirones like buspirone (via metabolite 1-PP) antagonize α₂-adrenergic receptors as well.

β	Agonists: 2-FNE 5-FNE Amibegron Arbutamine Arformoterol Arotinolol BAAM Bambuterol Befunolol Bitolterol Broxaterol Buphenine Carbuterol Cimaterol Clenbuterol Denopamine Deterenol Dipivefrine Dobutamine Dopamine Dopexamine Ephedrine Epinephrine Etafedrine Etilefrine Ethylnorepinephrine Fenoterol Formoterol Hexoprenaline Higenamine Indacaterol Isoetarine Isoprenaline Isoxsuprine Levonordefrin Levosalbutamol Mabuterol Methoxyphenamine Methyldopa Mirabegron N-Isopropyloctopamine Norepinephrine Orciprenaline Oxyfedrine Phenylpropanolamine Pirbuterol Prenalterol Ractopamine Procaterol Pseudoephedrine Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vilanterol Xamoterol 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 Levocicloprolol Levomoprolol Medroxalol Mepindolol Metalol Metipranolol Metoprolol Moprolol Nadolol Nadoxolol Nafetolol Nebivolol Neraminol Nifenalol Nipradilol Oberadilol Oxprenolol Pacrinolol Pafenolol Pamatolol Pargolol Parodilol Penbutolol Penirolol PhQA-33 Pindolol Pirepolol Practolol Primidolol Procinolol Pronethalol Propafenone Propranolol Ridazolol Ronactolol Soquinolol Sotalol Spirendolol SR 59230A Sulfinalol TA-2005 Talinolol Tazolol Teoprolol Tertatolol Tienoxolol Tilisolol Timolol Tiprenolol Tolamolol Toliprolol Tribendilol Trigevolol Xibenolol Xipranolol

Reuptake inhibitors

NET	Selective norepinephrine reuptake inhibitors: Amedalin Atomoxetine (Tomoxetine) Ciclazindol Daledalin Edivoxetine Esreboxetine Lortalamine Mazindol Nisoxetine Reboxetine Talopram Talsupram Tandamine Viloxazine; Norepinephrine-dopamine reuptake inhibitors: Amineptine Bupropion Fencamine Fencamfamine Hydroxybupropion Lefetamine Levophacetoperane LR-5182 Manifaxine Methylphenidate Nomifensine O-2172 Radafaxine; Serotonin-norepinephrine reuptake inhibitors: Bicifadine Desvenlafaxine Duloxetine Eclanamine Levomilnacipran Milnacipran Sibutramine Venlafaxine; Serotonin-norepinephrine-dopamine reuptake inhibitors: Brasofensine Diclofensine DOV-102,677 DOV-21,947 DOV-216,303 JNJ-7925476 JZ-IV-10 Liafensine Methylnaphthidate Naphyrone NS-2359 Perafensine PRC200-SS SEP-225,289 SEP-227,162 Tesofensine; Tricyclic antidepressants: Amitriptyline Butriptyline Cianopramine Clomipramine Desipramine Dosulepin Doxepin Imipramine Lofepramine Melitracen Nortriptyline Protriptyline Trimipramine; Tetracyclic antidepressants: Amoxapine Maprotiline Mianserin Oxaprotiline Setiptiline; Others: Cocaine CP-39,332 Ethanol EXP-561 Fezolamine Ginkgo biloba Indeloxazine Nefazodone Nefopam Pridefrine Tapentadol Tedatioxetine Teniloxazine Tofenacin Tramadol Ziprasidone

VMAT	Ibogaine Reserpine Tetrabenazine

Releasing agents

Morpholines: Fenbutrazate
Fenmetramide
Morazone
Morforex
Phendimetrazine
Phenmetrazine
Pseudophenmetrazine; Oxazolines: 4-MAR
Aminorex
Clominorex
Cyclazodone
Fenozolone
Fluminorex
Pemoline
Thozalinone; Phenethylamines (also amphetamines, cathinones, etc): 2-OH-PEA
4-CAB
4-FA
4-FMA
4-MA
4-MMA
Alfetamine
Amfecloral
Amfepentorex
Amfepramone
Amphetamine (Dextroamphetamine
Levoamphetamine)
Amphetaminil
β-Me-PEA
BDB
Benzphetamine
BOH
Buphedrone
Bupropion
Butylone
Cathine
Cathinone
Clobenzorex
Clortermine
Dimethylamphetamine
Dimethylcathinone
DMA
DMMA
EBDB
Ephedrine
Ethcathinone
Ethylone
Etilamfetamine
Famprofazone
Fenethylline
Fenproporex
Flephedrone
Fludorex
Furfenorex
Hordenine
4-Hydroxyamphetamine
IAP
IMP
Iofetamine
Lisdexamfetamine
Lophophine
MBDB
MDA
MDEA
MDMA
MDMPEA
MDOH
MDPEA
Mefenorex
Mephedrone
Mephentermine
Methamphetamine (Dextromethamphetamine
Levomethamphetamine)
Methcathinone
Methedrone
Methylone
Morforex
Naphthylisopropylamine
Ortetamine
pBA
pCA
Pentorex
Phenethylamine
Pholedrine
Phenpromethamine
Phentermine
Phenylpropanolamine
pIA
Prenylamine
Propylamphetamine
Pseudoephedrine
Selegiline (also D-Deprenyl)
Tiflorex
Tyramine
Xylopropamine
Zylofuramine; Piperazines: 2C-B-BZP
BZP
MBZP
mCPP
MDBZP
MeOPP
pFPP; Others: 2-ADN
2-AI
2-AT
2-BP
4-BP
5-IAI
Clofenciclan
Cyclopentamine
Cypenamine
Cyprodenate
Feprosidnine
Gilutensin
Heptaminol
Hexacyclonate
Indanorex
Isometheptene
Methylhexanamine
Octodrine
Phthalimidopropiophenone
Propylhexedrine (Levopropylhexedrine)
Tuaminoheptane

Enzyme inhibitors

Anabolism

PAH	3,4-Dihydroxystyrene

TH	3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone

AAAD	Benserazide Carbidopa DFMD Genistein Methyldopa

DBH	Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone

PNMT	CGS-19281A SKF-64139 SKF-7698

Catabolism

MAO	Nonselective: Benmoxin Caroxazone Echinopsidine Furazolidone Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivalylbenzhydrazine Procarbazine Safrazine Tranylcypromine; MAO-A selective: Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline Eprobemide Esuprone Harmala alkaloids (Harmine, Harmaline Tetrahydroharmine Harman Norharman, etc) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone Tyrima; MAO-B selective: Ladostigil Lazabemide Milacemide Mofegiline Pargyline Rasagiline Safinamide Selegiline (also D-Deprenyl) * Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the breakdown of their precursor dopamine.

COMT	Entacapone Nitecapone Tolcapone

Others

Precursors	L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) → Dopamine L-DOPS (Droxidopa)

Cofactors	Ferrous Iron (Fe²⁺) S-Adenosyl-L-Methionine Vitamin B₃ (Niacin Nicotinamide → NADPH) Vitamin B₆ (Pyridoxine Pyridoxamine Pyridoxal → Pyridoxal Phosphate) Vitamin B₉ (Folic acid → Tetrahydrofolic acid) Vitamin C (Ascorbic acid) Zinc (Zn²⁺)

Others	Activity enhancers: BPAP PPAP; Release blockers: Bethanidine Bretylium Guanadrel Guanazodine Guanclofine Guanethidine Guanoxan; Toxins: 6-OHDA

List of adrenergic drugs

Dopaminergics

Receptor ligands

Agonists	Adamantanes: Amantadine Memantine Rimantadine; Aminotetralins: 7-OH-DPAT 8-OH-PBZI Rotigotine UH-232; Benzazepines: 6-Br-APB Fenoldopam SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959; Ergolines: Bromocriptine Cabergoline Dihydroergocryptine Epicriptine Lisuride LSD Pergolide; Dihydrexidine derivatives: 2-OH-NPA A-86,929 Ciladopa Dihydrexidine Dinapsoline Dinoxyline Doxanthrine; Others: A-68,930 A-77636 A-412,997 ABT-670 ABT-724 Aplindore Apomorphine Aripiprazole Bifeprunox BP-897 CY-208,243 Dizocilpine Etilevodopa Flibanserin Ketamine Melevodopa Modafinil Pardoprunox Phencyclidine PD-128,907 PD-168,077 PF-219,061 Piribedil Pramipexole Propylnorapomorphine Pukateine Quinagolide Quinelorane Quinpirole RDS-127 Ro10-5824 Ropinirole Rotigotine Roxindole Salvinorin A SKF-89,145 Sumanirole Terguride Umespirone WAY-100,635

Antagonists	Typical antipsychotics: Acepromazine Azaperone Benperidol Bromperidol Clopenthixol Chlorpromazine Chlorprothixene Droperidol Flupentixol Fluphenazine Fluspirilene Haloperidol Levosulpiride Loxapine Mesoridazine Methotrimeprazine Nemonapride Penfluridol Perazine Periciazine Perphenazine Pimozide Prochlorperazine Promazine Sulforidazine Sulpiride Sultopride Thioridazine Thiothixene Trifluoperazine Triflupromazine Trifluperidol Zuclopenthixol; Atypical antipsychotics: Amisulpride Asenapine Blonanserin Cariprazine Carpipramine Clocapramine Clorotepine Clozapine Gevotroline Iloperidone Lurasidone Melperone Molindone Mosapramine Olanzapine Paliperidone Perospirone Piquindone Quetiapine Remoxipride Risperidone Sertindole Tiospirone Zicronapine Ziprasidone Zotepine; Antiemetics: AS-8112 Alizapride Bromopride Clebopride Domperidone Metoclopramide Thiethylperazine; Others: Amoxapine Buspirone Butaclamol Ecopipam EEDQ Eticlopride Fananserin Hydroxyzine L-745,870 Nafadotride Nuciferine PNU-99,194 Raclopride Sarizotan SB-277,011-A SCH-23,390 SKF-83,959 Sonepiprazole Spiperone Spiroxatrine Stepholidine Tetrahydropalmatine Tiapride UH-232 Yohimbine

Modulators	see template "Allosteric modulators"

Reuptake inhibitors

Plasmalemmal

DAT inhibitors

Piperazines: DBL-583
GBR-12,935
Nefazodone
Vanoxerine; Piperidines: BTCP
Desoxypipradrol
Dextromethylphenidate
Difemetorex
Ethylphenidate
Methylnaphthidate
Methylphenidate
Phencyclidine
Pipradrol; Pyrrolidines: Diphenylprolinol
MDPV
Naphyrone
Prolintane
Pyrovalerone; Tropanes: Altropane
Brasofensine
CFT
Cocaine
Dichloropane
Difluoropine
FE-β-CPPIT
FP-β-CPPIT
Ioflupane (¹²³I)
Iometopane
RTI-112
RTI-113
RTI-121
RTI-126
RTI-150
RTI-177
RTI-229
RTI-336
Tenocyclidine
Tesofensine
Troparil
Tropoxane
WF-11
WF-23
WF-31
WF-33; Others: Adrafinil
Armodafinil
Amfonelic acid
Amphetamine
Amineptine
Benzatropine
Bromantane
BTQ
BTS-74,398
Bupropion
Ciclazindol
Diclofensine
Dimethocaine
Diphenylpyraline
Dizocilpine
DOV-102,677
DOV-21,947
DOV-216,303
Etybenzatropine
EXP-561
Fencamine
Fencamfamine
Fezolamine
Fluorenol
GYKI-52,895
Indatraline
Ketamine
Lefetamine
Levophacetoperane
Liafensine
LR-5182
Manifaxine
Mazindol
Medifoxamine
Mesocarb
Modafinil
Nefopam
Nomifensine
NS-2359
O-2172
Perafensine
Pridefrine
Radafaxine
SEP-225,289
SEP-227,162
Sertraline
Sibutramine
Tametraline
Tedatioxetine
Tripelennamine

Vesicular

VMAT inhibitors	Deserpidine Ibogaine Reserpine Tetrabenazine

Releasing agents

Morpholines: Fenbutrazate
Fenmetramide
Morazone
Morforex
Phendimetrazine
Phenmetrazine
Pseudophenmetrazine; Oxazolines: 4-MAR
Aminorex
Clominorex
Cyclazodone
Fenozolone
Fluminorex
Pemoline
Thozalinone; Phenethylamines (also amphetamines, cathinones, etc): 2-OH-PEA
4-CAB
4-FA
4-FMA
4-MA
4-MMA
Alfetamine
Amfecloral
Amfepentorex
Amfepramone
Amphetamine (Dextroamphetamine
Levoamphetamine)
Amphetaminil
β-Me-PEA
BDB
BOH
Benzphetamine
Buphedrone
Bupropion
Butylone
Cathine
Cathinone
Clobenzorex
Clortermine
D-Deprenyl
DMA
DMMA
Dimethylamphetamine
Dimethylcathinone
Ephedrine
Ethcathinone
EBDB
Ethylone
Etilamfetamine
Famprofazone
Fenethylline
Fenproporex
Flephedrone
Fludorex
Furfenorex
Hordenine
4-Hydroxyamphetamine
Iofetamine
Lophophine
Mefenorex
Mephedrone
Methamphetamine (Dextromethamphetamine, Levomethamphetamine)
Methcathinone
Methedrone
MMDA
MMDMA
MBDB
MDA
MDEA
MDMA
MDMPEA
MDOH
MDPEA
Methylone
Morforex
Ortetamine
pBA
pCA
pIA
Pholedrine
Phenethylamine
Pholedrine
Phenpromethamine
Prenylamine
Propylamphetamine
Pseudoephedrine
Tiflorex
Tyramine
Xylopropamine
Zylofuramine; Piperazines: 2C-B-BZP
BZP
MBZP
MDBZP
MeOPP; Others: 2-ADN
2-AI
2-AT
4-BP
5-IAI
Clofenciclan
Cyclopentamine
Cypenamine
Cyprodenate
Feprosidnine
Gilutensin
Heptaminol
Hexacyclonate
IAP
Indanorex
Isometheptene
Methylhexanamine
Naphthylisopropylamine
Octodrine
Phthalimidopropiophenone
Propylhexedrine (Levopropylhexedrine)
Tuaminoheptane

Allosteric modulators

Receptors	SB-269,652

Transporter	Quinazolinamines: SoRI-9804 SoRI-20040 SoRI-20041

Enzyme inhibitors

Anabolism

PAH inhibitors	3,4-Dihydroxystyrene

TH inhibitors	3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone

AAAD/DDC inhibitors	Benserazide Carbidopa DFMD Genistein Methyldopa

Catabolism

MAO inhibitors	Nonselective: Benmoxin Caroxazone Echinopsidine Furazolidone Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivalylbenzhydrazine Procarbazine Safrazine Tranylcypromine; MAO-A selective: Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline Eprobemide Esuprone Harmala alkaloids Methylene Blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone Tyrima; MAO-B selective: D-Deprenyl Ethanol L-Deprenyl (Selegiline) Ladostigil Lazabemide Milacemide Nicotine Pargyline^‡ Rasagiline Safinamide

COMT inhibitors	Entacapone Nitecapone Tolcapone

DBH inhibitors	Disulfiram Dopastin Fusaric acid Nepicastat Tropolone

Others

Precursors	L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa)

Cofactors	Ferrous iron (Fe²⁺) Tetrahydrobiopterin Vitamin B₃ (Niacin Nicotinamide → NADPH) Vitamin B₆ (Pyridoxine Pyridoxamine Pyridoxal → Pyridoxal phosphate) Vitamin B₉ (Folic acid → Tetrahydrofolic acid) Vitamin C (Ascorbic acid) Zinc (Zn²⁺)

Others	Activity enhancers: BPAP * PPAP; Toxins: 6-OHDA; Steroids: Anabolic-androgenic steroids

List of dopaminergic drugs

GABAergics

Receptor
(ligands)

GABA_A	Agonists: Main site: Bamaluzole Gaboxadol Ibotenic acid Isoguvacine Isonipecotic acid Muscimol (Amanita muscaria) Picamilon Piperidine-4-sulfonic acid Progabide Quisqualamine SL 75102 Thiomuscimol Tolgabide; Positive allosteric modulators: Alcohols Barbiturates Benzodiazepines Carbamates Chlormezanone Clomethiazole Imidazoles Kavalactones (kava) Lanthanum Loreclezole Neuroactive steroids Niacin/niacinamide Nonbenzodiazepines (β-carbolines, cyclopyrrolones, imidazopyridines, pyrazolopyrimidines, etc.) Phenols Piperidinediones Propanidid Pyrazolopyridines Quinazolinones ROD-188 Skullcap Stiripentol Valerenic acid (valerian) Note: See for a full list of GABA_A PAMs. Antagonists: Main site: Bicuculline Coriamyrtin Dihydrosecurinine Gabazine Hydrastine Hyenachin (mellitoxin) Pitrazepin Securinine Sinomenine Thiocolchicoside Tutin; Negative allosteric modulators: 17-Phenylandrostenol α5IA (LS-193,268) Anisatin β-Lactams (penicillins, cephalosporins, carbapenems) Bemegride Bilobalide Cicutoxin Cyclothiazide DHEA DHEA-S DMCM FG-7142 (ZK-31906) Fipronil Flumazenil Fluoroquinolones (e.g., ciprofloxacin) Flurothyl Furosemide Iomazenil (¹²³I) Isopregnanolone (sepranolone) L-655,708 Leptazol Lindane Morphine Naloxone Naltrexone Oenanthotoxin Pentetrazol (metrazol) Phenylsilatrane Picrotoxin (picrotin, picrotoxinin) Pregnenolone sulfate PWZ-029 Radequinil RG-1662 Ro15-4513 Ro4938581 Sarmazenil Suritozole TB-21007 Terbequinil TETS Thujone U-93631 Zinc ZK-93426

GABA_A-ρ	Agonists: Main site: CACA CAMP GABOB N⁴-Chloroacetylcytosine arabinoside Picamilon Progabide Tolgabide Antagonists: Main site: Bilobalide TPMPA

GABA_B	Agonists: Main site: 1,4-Butanediol Aceburic acid Baclofen GBL GHB GHV GVL Lesogaberan Phenibut Picamilon Progabide SKF-97,541 Tolgabide; Positive allosteric modulators: BHF-177 BHFF BSPP CGP-7930 GS-39783 Antagonists: Main site: CGP-35348 Phaclofen Saclofen SCH-50911

Transporter
(blockers)

GAT	CI-966 Deramciclane EF-1502 Gabaculine Guvacine Nipecotic acid NNC 05-2090 SKF-89976A SNAP-5114 Tiagabine

VGAT	Nipecotic acid Vigabatrin

Enzyme
(inhibitors)

GAD	Allylglycine

GABA-T	3-Hydrazinopropionic acid Aminooxyacetic acid Gabaculine Isoniazid Phenelzine Phenylethylidenehydrazine Rosmarinic acid (lemon balm) Sodium valproate Valnoctamide Valproate pivoxil Valproate semisodium (divalproex sodium) Valproic acid Valpromide Vigabatrin

Others

Cofactors: Vitamin B₆

Phenethylamines

Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-FLY βk-2C-B 2C-C 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-I 2C-N 2C-P 2C-SE 2C-T 2C-T-2 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-17 2C-T-21 2C-TFM 2C-YN Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA

Amphetamines	Psychedelics: 3C-BZ 3C-E 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA Stimulants: 3-FMA 4-MA 4-MMA 4-MTA 5-IT Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamine Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine Oxifentorex Oxilofrine Ortetamine PBA PCA Phenpromethamine PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 5-APB 5-APDB 5-MAPB 6-APB 6-APDB 6-MAPB EDA IAP MDA MDEA MDHMA MDMA MDOH MMDMA NAP TAP Others: Amiflamine DFMDA Selegiline (also D-Deprenyl)

Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH

Cathinones	Stimulants: Amfepramone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Flephedrone Hydroxybupropion Methcathinone Mephedrone Methedrone Radafaxine Entactogens: Ethylone Methylone

Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine

Phenylalkylpyrrolidines	Stimulants: a-PBP a-PPP a-PVP MDPBP MDPPP MDPV MOPPP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone

Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine

Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Etafedrine ETH-LAD Famprofazone Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Theodrenaline Thiamphenicol UWA-101

Amfecloral

Amfecloral

Synthesis

See also

References

Categories

Amphetamine

Encyclopedia Article

Methamphetamine

Encyclopedia Article

Zinc

Encyclopedia Article

Norepinephrine

Encyclopedia Article

Suggestions

Fenbutrazate

Encyclopedia Article

Etilamfetamine

Encyclopedia Article

Fencamine

Encyclopedia Article

3,4-Dimethylmethcathinone

Encyclopedia Article

3-Fluoromethcathinone

Encyclopedia Article