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Diethylpropion

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Diethylcathinone
Systematic (IUPAC) name
2-(diethylamino)-1-phenylpropan-1-one
Identifiers
CAS number	90-84-6
ATC code	A08AA03
PubChem	7029
Chemical data
Formula	C₁₃H₁₉N O
Mol. mass	205.30
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	B
Legal status	Schedule IV(US)
Routes	?

Diethylcathinone (also called Diethylpropion and Amfepramone), is a sympathomimetic stimulant drug marketed as an appetite suppressant. It is sold under the brand name Tenuate or Tenuate Dospan, and may also be known as Amfepramone. The popular antidepressant, bupropion (Wellbutrin) is an analogue of this chemical. Both diethylpropion and bupropion have a stimulant effect on the central nervous system.

Contents

1 Pharmacology
2 Contraindications
3 Side effects
4 See also
5 References

Pharmacology

Diethylpropion is a prodrug.^[1] It does not become bioactive until one of the N-ethyl groups in the chemical structure has become dealkylated in vivo.^[1]

(Di)ethylpropion is quite a weak dopaminergic this is in contrast to other monoaminergic based appetite suppressants such as sibutramine, phentermine and dextroamphetamine.

Apparently, it has been found to be potentially neurotoxic in that it causes long-term depletions of 5-HT similar to MDMA.^[2] This is somewhat unexpected since neither diethylpropion nor ethylpropion are serotonin releasers.^[1] Additionally, ethylpropion only weakly interacts with the SERT (K_i >2000nM) whereas diethypropion is completely active at this transporter.^[1]

Appetite Suppressants and their Metabolites
Test Drug	Release NET EC₅₀ (nM ± SD)	NE Uptake K_i (nM ± SD)	Release DAT EC₅₀ (nM ± SD)	DA Uptake K_i (nM ± SD)	Release SERT EC₅₀ (nM ± SD)	5-HT Uptake K_i (nM ± SD)
Phentermine	39.4 ± 6.6	-	262 ± 21	-	3,511 ± 253	-
(+)-Amphetamine	7.07 ± 0.95	-	24.8 ± 3.5	-	1,765 ± 94	-
Diethylpropion	>10,000	>10,000	>10,000	>10,000	>10,000	>10,000
N-Ethylpropion	99.3 ± 6.6	-	-	1,014 ± 80	2,118 ± 98	-
Phendimetrazine	8,300 ± 445	>10,000	19,000 ± 537	>10,000	>100,000	>100,000
Phenmetrazine	50.4 ± 5.4	-	131 ± 11	-	7,765 ± 610	-

Chemically, it is the N,N-diethyl homologue of cathinone and dimethylcathinone.

Diethylpropion is manufactured in 25 mg tablets and 75 mg controlled-release tablets (Tenuate, Tepanil Ten-Tab).

Diethylpropion is classified as a Schedule IV controlled substance in the United States.

It is also used in the treatment of migraine (off-label).

Contraindications

Hypersensitivity to sympathomimetic amines
Advanced arteriosclerosis or symptomatic cardiovascular disease
Moderate or severe hypertension
Hyperthyroidism
History of drug abuse
MAO inhibitor use (within 14 days)

Side effects

Severe

Insomnia
Pulmonary hypertension
Stroke
Psychosis

Cardiovascular

Tachycardia, hypertension, arrhythmia, chest pain

Ear, nose, and throat

Xerostomia, metallic taste

Endocrine

Changes in libido, gynecomastia, menstrual irregularities

Eye

Blurred vision

Gastrointestinal

Nausea/vomiting, constipation, abdominal cramps

Hematological

Bone marrow depression, agranulocytosis, leukopenia

Neurological

Tremor

Psychological

Euphoria, agitation, nervousness, restlessness, dizziness, anxiety, headache, mental depression, seizures

Skin

Rash, hives, alopecia, ecchymosis

Urogenital and reproductive

Changes in libido, impotence

See also

References

^ ^a ^b ^c ^d Rothman RB, Baumann MH. Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006;6(17):1845-59. PMID 17017961
^ Kleven et al., unpublished data Methamphetamine-induced Neurotoxicity: Structure Activity Relationships Annals of the New York Academy of Sciences Volume 654, pg 292301

v d e Stimulants

Adamantanes	Adaphenoxate Adapromine Amantadine Bromantane Chlodantane Gludantane Memantine Midantane

Arylcyclohexylamines	Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine

Benzazepines	6-Br-APB SKF-81297 SKF-82958

Cholinergics	A-84543 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

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

Eugeroics	Adrafinil Armodafinil Modafinil

Oxazolines	4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone

Phenethylamines	2-Fluoroamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2-Phenyl-3-methylaminobutane 2,3-MDA 3-Fluoroamphetamine 3-Methoxyamphetamine 3-Methylamphetamine 4-BMC 4-Ethylamphetamine 4-FA 4-FMA 4-MA 4-MMA 4-MTA Alfetamine -Ethylphenethylamine Amfepentorex Amidephrine Amphechloral Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine Atomoxetine (Tomoxetine) -Methylphenethylamine Benfluorex Benzphetamine BDB (J) BOH (Hydroxy-J) BPAP Buphedrone Bupropion (Amfebutamone) Butylone Cathine Cathinone Chlorphentermine Clenbuterol Clobenzorex Clortermine Denopamine Dibutylone Diethylcathinone (Diethylpropion, Amfepramone) Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone (Dimethylpropion, Metamfepramone) Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB (Ethyl-J) Ephedrine Epinephrine (Adrenaline) Epinine (Deoxyepinephrine) Etafedrine Ethcathinone (Ethylpropion) Ethylamphetamine (Etilamfetamine) Ethylone Etilefrine Fenbutrazate Fencamine Fencamfamine Fenethylline Fenfluramine (Dexfenfluramine) Fenproporex Flephedrone Fludorex Furfenorex Gepefrine HMMA Hordenine Ibopamine Indanorex IMP Indanylamphetamine Isoetarine Isoprenaline (Isoproterenol) Lefetamine Lisdexamfetamine Lophophine (Homomyristicylamine) Manifaxine MBDB (Methyl-J; "Eden") MDA (Tenamfetamine) MDBU MDEA ("Eve") MDMA ("Ecstasy", "Adam") MDMPEA (Homarylamine) MDOH MDPR MDPEA (Homopiperonylamine) Medifoxamine Mefenorex Mephedrone Mephentermine Metanephrine Metaraminol Methamphetamine (Desoxyephedrine, Methedrine; Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methcathinone (Methylpropion) Methedrone Methoxyphenamine Methylone MMDA MMDMA MMMA Naphthylamphetamine Nisoxetine Norepinephrine (Noradrenaline) Norfenefrine Norfenfluramine Normetanephrine Octopamine Orciprenaline Ortetamine Oxaflozane Oxilofrine Paredrine (Norpholedrine, Oxamphetamine, Mycadrine) PBA PCA PHA Pargyline Phendimetrazine Phenmetrazine Phenpentermine Phenpromethamine Phentermine Phenylalanine Phenylephrine (Neosynephrine) Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Propylamphetamine Pseudoephedrine Radafaxine Ropinirole Salbutamol (Albuterol; Levosalbutamol) Selegiline (Deprenyl) Sibutramine Synephrine (Oxedrine) Theodrenaline Tiflorex (Flutiorex) Tranylcypromine Tyramine Tyrosine Xamoterol Xylopropamine Zylofuramine

Piperazines	2C-B-BZP BZP DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 MeOPP MBZP Vanoxerine

Piperidines	2-Benzylpiperidine 4-Benzylpiperidine Desoxypipradrol Diphemethoxidine Ethylphenidate Methylnaphthidate Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol SCH-5472

Pyrrolidines	-PPP -PBP -PVP MDPPP MDPBP MDPV MPBP MPHP MPPP MOPPP Naphyrone Prolintane Pyrovalerone

Tropanes	3-Bis-(4-fluorophenyl)methoxytropane 3-CPMT 3-Pseudotropyl-4-fluorobenzoate Altropane (IACFT) Brasofensine CFT (WIN 35,428) -CIT (RTI-55) Cocaethylene Cocaine -CPPIT Dichloropane (RTI-111) Difluoropine FE--CPPIT FP--CPPIT Ioflupane (FPCIT) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-171 RTI-177 RTI-336 RTI-371 RTI-386 Tesofensine Troparil (-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33 WF-60

Xanthines	Aminophylline Caffeine Dimethazan Paraxanthine Theobromine Theophylline

Others	1-(Thiophen-2-yl)-2-aminopropane 2-Aminoindane 2-Aminotetralin 2-Diphenylmethylpyrrolidine 5-(2-Aminopropyl)indole AL-1095 Amfonelic acid Amineptine Amiphenazole Atipamezole Bemegride Benzydamine BTQ BTS 74,398 Carphedon Clofenciclan Cropropamide Crotetamide Diclofensine Dimethocaine Diphenylprolinol Efaroxan Etamivan Feprosidnine Gamfexine Gilutensin GYKI-52895 Hexacyclonate Idazoxan Indatraline JNJ-7925476 JZ-IV-10 Lazabemide Leptacline LR-5182 Mazindol Meclofexonate Mefexamide Mesocarb Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline Phthalimidopropiophenone Propylhexedrine PRC200-SS Rasagiline Rauwolscine Tametraline Tandamine U-23807A UH-232 Yohimbine

See also Sympathomimetic amines

Antiobesity Agents / Anorectics (A08)

Stimulants	4-Methylamphetamine Amfepentorex Aminorex Amphetamine Amphetaminil Atomoxetine Benfluorex Benzphetamine Bupropion Cathine Cathinone Chlorphentermine Clobenzorex Clominorex Clortermine Dexfenfluramine Dextroamphetamine Dextromethamphetamine Dexmethylphenidate Diethylcathinone Dimethylcathinone Diphemethoxidine Ephedrine Ephedra Ethylamphetamine Fencamfamine Fenethylline Fenfluramine Fenproporex Fludorex Fluminorex Furfenorex Indanorex Khat Lisdexamfetamine Manifaxine Mazindol Mefenorex Methamphetamine Methylphenidate Pemoline Phendimetrazine Phenethylamine Phenmetrazine Phenpentermine Phentermine Phenylpropanolamine Pipradrol Prolintane Pseudoephedrine Pyrovalerone Radafaxine Reboxetine Sibutramine Synephrine Tesofensine Viloxazine Xylopropamine Zylofuramine

Cannabinoids	Ibipinabant Otenabant Rimonabant 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

Peripheral

Cetilistat Dinitrophenol Oleoyl-Estrone Orlistat Simmondsin Sterculia

Receptor
Ligands

Agonists	Benzazepines: 6-Br-APB Fenoldopam SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959; Ergot-derivatives: Bromocriptine Cabergoline Dihydroergocryptine Lisuride LSD Pergolide; Dihydrexidine-derivatives: 2-OH-NPA A-86,929 Dihydrexidine Dinapsoline Dinoxyline Doxanthrine; Morphine-derivatives: Apomorphine Propylnorapomorphine; Piperazines: ABT-724 Aripiprazole Piribedil WAY-100,635; Others: 7-OH-DPAT 8-OH-PBZI A-68,930 A-77,636 A-412,997 ABT-670 Amantadine Aplindore CY-208,243 Memantine PD-128,907 PF-219,061 Pramipexole Pukateine Quinpirole RDS-127 Rimantadine Ropinirole Rotigotine SKF-89145 SKF-89626

Antagonists	Typical Antipsychotics: Acepromazine Azaperone Benperidol Bromperidol Clopenthixol Chlorpromazine Chlorprothixene Droperidol Flupentixol Fluphenazine Fluspirilene Haloperidol Loxapine Mesoridazine Methotrimeprazine Molindone Penfluridol Perazine Periciazine Perphenazine Pimozide Prochlorperazine Promazine Sulforidazine Thioridazine Thiothixene Trifluoperazine Triflupromazine Trifluperidol Zuclopenthixol; Atypical Antipsychotics: Amisulpride Asenapine Clozapine Iloperidone Melperone Olanzapine Paliperidone Perospirone Quetiapine Risperidone Sertindole Sulpiride Ziprasidone Zotepine; Antiemetics: AS-8112 Alizapride Bromopride Clebopride Domperidone Metoclopramide Thiethylperazine; Others: Amoxapine Blonanserin Buspirone Butaclamol N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline Ecopipam Eticlopride Fananserin Mosapramine Nafadotride Nemonapride Nuciferine Raclopride Remoxipride SB-277,011-A SCH-23,390 SKF-83,566 Spiperone Spiroxatrine Stepholidine Tetrahydropalmatine Tiapride UH-232 Yohimbine

Reuptake
Inhibitors

DAT Inhibitors	Piperazines: DBL-583 GBR-12,935 Nefazodone Vanoxerine; Piperidines: BTCP Desoxypipradrol Dextromethylphenidate Ethylphenidate Methylnaphthidate Methylphenidate Phencyclidine Pipradrol; Pyrrolidines: Diphenylprolinol Methylenedioxypyrovalerone (MDPV) Naphyrone Prolintane Pyrovalerone; Tropanes: -CPPIT Altropane Brasofensine CFT Cocaine Dichloropane Difluoropine FE--CPPIT FP--CPPIT Ioflupane Iometopane RTI-112 RTI-113 RTI-121 RTI-126 RTI-150 RTI-177 RTI-336 Tenocyclidine Tesofensine Troparil Tropoxane WF-11 WF-23 WF-31 WF-33; Others: Amfonelic Acid Amineptine Benzatropine Bromantane BTQ BTS-74,398 Bupropion (Amfebutamone) Diclofensine Dimethocaine Dizocilpine DOV-102,677 DOV-21,947 DOV-216,303 Etybenzatropine Fencamine Fencamfamine GYKI-52,895 Indatraline Ketamine Lefetamine LR-5182 Manifaxine Medifoxamine Mesocarb Nefopam Nomifensine NS-2359 O-2172 Propylamphetamine Radafaxine SEP-225,289 SEP-227,162 Sibutramine Tametraline Tripelennamine

TRPC6 Activators	Adhyperforin Hyperforin

VMAT Inhibitors

Deserpidine Ibogaine Reserpine Tetrabenazine

Releasing
Agents

Oxazolines: 4-Methylaminorex (4-MAR, 4-MAX) Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone; Phenethylamines (also Amphetamines, Cathinones, Phentermines, etc): 2-Hydroxyphenethylamine (2-OH-PEA) 4-Methylamphetamine (4-MA) 4-Methylmethamphetamine (4-MMA) -Ethylphenethylamine (-Et-PEA) Alfetamine Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Amfepentorex -Methylphenethylamine (-Me-PEA) Benzodioxolylbutanamine (BDB) Benzodioxolylhydroxybutanamine (BOH) Benzphetamine Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine Diethylcathinone (Diethylpropion, Amfepramone) Dibutylone Dimethoxyamphetamine (DMA) Dimethoxymethamphetamine (DMMA) Dimethylamphetamine Dimethylcathinone (Dimethylpropion, Metamfepramone) Ethcathinone (Ethylpropion) Ethylamphetamine Ethylbenzodioxolylbutanamine (EBDB) Ethylone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine Indanorex Indanylamphetamine (IAP) Lophophine (Homomyristicylamine) Mefenorex Mephedrone Methamphetamine (Desoxyephedrine, Methedrine; Dextromethamphetamine, Levomethamphetamine) Methcathinone (Methylpropion) Methedrone Methoxymethylenedioxyamphetamine (MMDA) Methoxymethylenedioxymethamphetamine (MMDMA) Methylbenzodioxolylbutanamine (MBDB) Methylenedioxyamphetamine (MDA; Tenamfetamine) Methylenedioxyethylamphetamine (MDEA) Methylenedioxyhydroxyamphetamine (MDOH) Methylenedioxymethamphetamine (MDMA) Methylenedioxymethylphenethylamine (MDMPEA; Homarylamine) Methylenedioxyphenethylamine (MDPEA; Homopiperonylamine) Methylone Naphthylamphetamine (NAP) Ortetamine Oxaflozane Parabromoamphetamine (PBA) Parachloroamphetamine (PCA) Parafluoroamphetamine (PFA) Parafluoromethamphetamine (PFMA) Parahydroxyamphetamine (PHA) Paraiodoamphetamine (PIA) Paramethoxyamphetamine (PMA) Paramethoxyethylamphetamine (PMEA) Paramethoxymethamphetamine (PMMA) Paredrine (Norpholedrine, Oxamphetamine) Phendimetrazine Phenethylamine (PEA) Phenmetrazine Pholedrine Phenpromethamine Propylamphetamine Tiflorex (Flutiorex) Tyramine (TRA) Xylopropamine Zylofuramine; Piperazines: 2,5-Dimethoxy-4-bromobenzylpiperazine (2C-B-BZP) Benzylpiperazine (BZP) Methoxyphenylpiperazine (MeOPP; Paraperazine) Methylbenzylpiperazine (MBZP) Methylenedioxybenzylpiperazine (MDBZP; Piperonylpiperazine); Others: 2-Aminoindane (2-AI) 2-Aminotetralin (2-AT) 4-Benzylpiperidine (4-BP) Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Isometheptene Methylhexanamine Octodrine Phthalimidopropiophenone Propylhexedrine (PHX) Tuaminoheptane (Tuamine)

Enzyme
Inhibitors

PAH Inhibitors	3,4-Dihydroxystyrene

TH Inhibitors	3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone

AAAD / DDC Inhibitors	Benserazide Carbidopa Methyldopa

MAO Inhibitors (MAOIs)	Nonselective: Iproclozide Iproniazid Isocarboxazid Nialamide Phenelzine Pheniprazine Tranylcypromine; MAO-A Selective: Befloxatone Brofaromine Cimoxatone Clorgiline Harmala Alkaloids Minaprine Moclobemide Pirlindole Toloxatone Tyrima; MAO-B Selective: Lazabemide Pargyline Rasagiline Selegiline

COMT Inhibitors	Entacapone Tolcapone

DBH Inhibitors	Disulfiram 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: Benzofuranylpropylaminopentane (BPAP) Phenylpropylaminopentane (PPAP)

Receptor
Ligands

5-HT_1A	Agonists: Azapirones: Alnespirone Binospirone Buspirone Eptapirone Gepirone Ipsapirone Perospirone Tandospirone Tiospirone Zalospirone; Lysergamides: Dihydroergotamine Ergotamine Methysergide LSD; Phenethylamines: MDA MDMA; Piperazines: Eltoprazine Flesinoxan Flibanserin; Tryptamines: 5-CT 5-MeO-DMT 5-MT DMT Psilocin Psilocybin Rauwolscine Yohimbine; Atypical Antipsychotics: Aripiprazole Asenapine Clozapine Quetiapine Ziprasidone; Others: 8-OH-DPAT Befiradol F-11440 Lesopitron Lu AA21004 LY-293,284 LY-301,317 MKC-242 Osemozotan Piclozotan PRX-00023 Repinotan RU-24969 S-15535 Sarizotan SSR-181,507 Sunepitron U-92016A Urapidil Vilazodone Xaliproden Antagonists: Beta Blockers: Alprenolol Cyanopindolol Iodocyanopindolol Oxprenolol Pindobind Pindolol Propranolol; Piperazines: Nefazodone Trazodone WAY-100,135 WAY-100,635; Others: AV965 BMY-7378 Dotarizine GR-46611 Isamoltane Lecozotan Methiothepin MPPF NAN-190 Robalzotan S-15535 SB-649915 SDZ 216-525 Spiperone Spiramide Spiroxatrine UH-301 WAY-100,135 WAY-100,635 Xylamidine

5-HT_1B	Agonists: Lysergamides: Dihydroergotamine Ergotamine Methysergide; Piperazines: Eltoprazine TFMPP; Triptans: Eletriptan Sumatriptan Zolmitriptan; Tryptamines: 5-CT 5-MT; Others: CP-93,129 CP-94,253 CP-135,807 RU-24969 Antagonists: Lysergamides: Metergoline Methiothepin; Tryptamines: Yohimbine; Others: AR-A000002 GR-127,935 Isamoltane SB-216,641 SB-224,289 SB-236,057

5-HT_1D	Agonists: Lysergamides: Dihydroergotamine Methysergide; Triptans: Almotriptan Eletriptan Frovatriptan Naratriptan Rizatriptan Sumatriptan Zolmitriptan; Tryptamines: 5-CT 5-MT; Others: CP-135,807 CP-286,601 GR-46611 L-694,247 L-772,405 PNU-109,291 PNU-142,633 Antagonists: Lysergamides: Metergoline Methiothepin; Tryptamines: Rauwolscine Yohimbine; Others: BRL-15572 GR-127,935 Ketanserin LY-310,762 LY-367,642 LY-456,219 LY-456,220 Ritanserin Ziprasidone

5-HT_1E	Agonists: Lysergamides: Methysergide; Triptans: Eletriptan; Tryptamines: Tryptamine Antagonists: Methiothepin

5-HT_1F	Agonists: Triptans: Eletriptan Naratriptan Sumatriptan; Tryptamines: 5-MT; Others: LY-334,370 Antagonists: Methiothepin

5-HT_2A	Agonists: Lysergamides: ALD-52 Ergonovine Lisuride LA-SS-Az LSD Lysergic acid 2-butyl amide Methysergide; Phenethylamines: 25I-NBMD 25I-NBOH 25I-NBOMe 2C-B 2C-B-FLY 2C-E 2C-I 2C-T-2 2C-T-7 2C-T-21 2CBCB-NBOMe 2CBFly-NBOMe Bromo-DragonFLY DOB DOC DOI DOM MDA MDMA Mescaline Myristicin TCB-2 TFMFly; Piperazines: BZP Quipazine TFMPP; Tryptamines: 5-CT 5-MeO--ET 5-MeO--MT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT 5-MeO-DPT 5-MT -ET -Methyl-5-HT -MT Bufotenin DET DiPT DMT DPT Psilocin Psilocybin; Others: AL-34662 AL-37350A PNU-22394 Antagonists: Atypical Antipsychotics: Amperozide Aripiprazole Clozapine Iloperidone Melperone Olanzapine Paliperidone Pimozide Quetiapine Risperidone Sertindole Ziprasidone Zotepine; Typical Antipsychotics: Loxapine Pipamperone; Antidepressants: Amitriptyline Amoxapine Etoperidone Mianserin Mirtazapine Nefazodone Trazodone; Others: 5-I-R91150 AC-90179 Altanserin AMDA APD-215 Blonanserin Cinanserin Cyproheptadine Deramciclane Dotarizine Eplivanserin Fananserin Flibanserin Ketanserin KML-010 Lubazodone Methiothepin Nantenine Pimavanserin Pizotifen Ritanserin Sarpogrelate Setoperone Spiperone Spiramide SR-46349B Volinanserin Xylamidine Yohimbine

5-HT_2B	Agonists: Oxazolines: 4-Methylaminorex Aminorex; Phenethylamines: Chlorphentermine DOB DOC DOI DOM Fenfluramine MDA MDMA Norfenfluramine; Tryptamines: 5-CT 5-MT -Methyl-5-HT; Others: BW-723C86 Cabergoline mCPP Pergolide PNU-22394 Ro60-0175 Antagonists: Agomelatine Asenapine EGIS-7625 Ketanserin Lisuride LY-272,015 Rauwolscine Ritanserin RS-127,445 Sarpogrelate SB-200,646 SB-204,741 SB-206,553 SB-215,505 SB-221,284 SB-228,357 SDZ SER-082 Tegaserod Yohimbine

5-HT_2C	Agonists: Phenethylamines: 2C-B 2C-E 2C-I 2C-T-2 2C-T-7 2C-T-21 DOB DOC DOI DOM MDA MDMA Mescaline Myristicin; Piperazines: Aripiprazole mCPP TFMPP; Tryptamines: 5-CT 5-MeO--ET 5-MeO--MT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT 5-MeO-DPT 5-MT -ET -Methyl-5-HT -MT Bufotenin DET DiPT DMT DPT Psilocin Psilocybin; Others: A-372,159 AL-38022A CP-809,101 Lorcaserin MK-212 PNU-22394 Ro60-0175 Vabicaserin WAY-629 WAY-161,503 YM-348 Antagonists: Atypical Antipsychotics: Clozapine Iloperidone Melperone Olanzapine Paliperidone Pimozide Quetiapine Risperidone Sertindole Ziprasidone Zotepine; Typical Antipsychotics: Chlorpromazine Loxapine Pipamperone; Antidepressants: Agomelatine Amitriptyline Amoxapine Etoperidone Fluoxetine Mianserin Mirtazapine Nefazodone Nortriptyline Trazodone; Others: Cinanserin Cyproheptadine Deramciclane Dimebolin Dotarizine Eltoprazine FR-260,010 Ketanserin Ketotifen Methysergide Pizotifen Ritanserin RS-102,221 SB-200,646 SB-206,553 SB-221,284 SB-228,357 SB-242,084 SB-243,213 SDZ SER-082 Xylamidine

Agonists: Piperazines: BZP Quipazine; Tryptamines: 2-Methyl-5-HT 5-CT; Others: Chlorophenylbiguanide RS-56812 SR-57,227 SR-57,227-A YM-31636
Antagonists: Antiemetics: AS-8112 Alosetron Azasetron Batanopride Bemesetron Cilansetron Dolasetron Granisetron Lerisetron Ondansetron Palonosetron Ramosetron Renzapride Tropisetron Zacopride Zatosetron; Atypical Antipsychotics: Clozapine Olanzapine Quetiapine; Tetracyclic Antidepressants: Amoxapine Mianserin Mirtazapine; Others: ICS-205,930 Lu AA21004 MDL-72,222 Memantine Ricasetron

Agonists: Gastroprokinetic Agents: Cisapride Metoclopramide Mosapride Prucalopride Renzapride Tegaserod Zacopride; Others: 5-MT BIMU-8 CJ-033,466 PRX-03140 RS-67333 RS-67506 TD-5108
Antagonists: GR-113,808 GR-125,487 L-Lysine Piboserod RS-39604 RS-67532 SB-203,186

5-HT_5A	Agonists: Lysergamides: Ergotamine LSD; Tryptamines: 5-CT; Others: Valerenic Acid Antagonists: Asenapine Dimebolin Methiothepin Ritanserin SB-699,551

5-HT_5B*	Agonists: Lysergamides: Ergotamine LSD Antagonists: Methiothepin * Note that the 5-HT_5B receptor is not functional in humans.

Agonists: Lysergamides: Lisuride LSD Metergoline; Tryptamines: 5-CT 5-MT E-6801 E-6837 EMD-386,088 EMDT LY-586,713 WAY-181,187 WAY-208,466
Antagonists: Antidepressants: Amitriptyline Amoxapine Clomipramine Doxepin Mianserin Nortriptyline; Atypical Antipsychotics: Aripiprazole Asenapine Clozapine Fluperlapine Iloperidone Olanzapine Tiospirone; Typical Antipsychotics: Chlorpromazine Loxapine; Others: BGC20-760 BVT-5182 BVT-74316 Dimebolin EGIS-12233 GW-742,457 Ketanserin Methiothepin MS-245 PRX-07034 Ritanserin Ro 04-6790 Ro 63-0563 SB-258,585 SB-271,046 SB-357,134 SB-399,885

Agonists: Lysergamides: LSD; Tryptamines: 5-CT 5-MT; Others: 8-OH-DPAT AS-19 Bifeprunox LP-12 LP-44 Sarizotan
Antagonists: Antidepressants: Amitriptyline Amoxapine Clomipramine Imipramine Maprotiline Mianserin; Atypical Antipsychotics: Amisulpride Aripiprazole Clozapine Olanzapine Risperidone Sertindole Tiospirone Ziprasidone Zotepine; Typical Antipsychotics: Chlorpromazine Loxapine; Others: EGIS-12233 LY-215,840 Mesulergine Metergoline Methiothepin Pimozide Ritanserin SB-258,719 SB-258,741 SB-269,970 SB-656,104 SB-656,104-A SB-691,673 SLV-313 SLV-314 Spiperone SSR-181,507

Reuptake
Inhibitors

SERT Inhibitors	Selective Serotonin Reuptake Inhibitors (SSRIs): Alaproclate Citalopram Dapoxetine Desmethylcitalopram Desmethylsertraline Escitalopram Femoxetine Fluoxetine Fluvoxamine Indalpine Litoxetine Lubazodone Norfluoxetine Paroxetine RTI-353 Sertraline Vilazodone Zimelidine; Serotonin-Norepinephrine Reuptake Inhibitors (SNRIs): Bicifadine Desvenlafaxine Duloxetine Milnacipran Venlafaxine; Serotonin-Norepinephrine-Dopamine Reuptake Inhibitors (SNDRIs): Brasofensine Diclofensine DOV-102,677 DOV-21,947 DOV-216,303 NS-2359 SEP-225,289 SEP-227,162 Tesofensine; Tricyclic Antidepressants (TCAs): Amitriptyline Butriptyline Cianopramine Clomipramine Desipramine Dosulepin Doxepin Imipramine Lofepramine Nortriptyline Protriptyline Trimipramine; Tetracyclic Antidepressants (TeCAs): Amoxapine; Piperazines: Nefazodone Trazodone; Antihistamines: Brompheniramine Chlorpheniramine Diphenhydramine Mepyramine (Pyrilamine) Pheniramine Tripelennamine; Opioids: Meperidine (Pethidine) Methadone Propoxyphene Tramadol; Others: Cocaine Cyclobenzaprine (CBZ) Dextromethorphan (DXM) Mesembrine Nefopam SB-649,915 Sibutramine Ziprasidone

TRPC6 Activators	Adhyperforin Hyperforin

VMAT Inhibitors

Ibogaine Reserpine Tetrabenazine

Releasing
Agents

Aminoindanes: Ethyltrifluoromethylaminoindane (ETAI) Methylenedioxyaminoindane (MDAI) Methylenedioxymethylaminoindane (MDMAI) Methoxymethylaminoindane (MMAI) Trifluoromethylaminoindane (TAI); Aminotetralins: 8-Hydroxydipropylaminotetralin (8-OH-DPAT); Oxazolines: 4-Methylaminorex (4-MAR, 4-MAX) Aminorex Clominorex Fluminorex; Phenethylamines (also Amphetamines, Cathinones, Phentermines, etc): 4-Methylthioamphetamine (4-MTA) 5-Aminopropyldihydrobenzofuran (5-APDB; 5-Desoxy-MDA) Benzodioxolylbutanamine (BDB) Benzodioxolylhydroxybutanamine (BOH) Brephedrone Butylone Chlorphentermine Dibutylone Diethylcathinone (Diethylpropion, Amfepramone) Dimethoxyamphetamine (DMA) Dimethoxymethamphetamine (DMMA) Dimethylcathinone (Dimethylpropion, Metamfepramone) Ethylbenzodioxolylbutanamine (EBDB) Ethylone Fenfluramine (Dexfenfluramine) Flephedrone Indanylamphetamine (IAP) Lophophine (Homomyristicylamine) Mephedrone Methedrone Methoxymethylamphetamine (MMA) Methoxymethylenedioxyamphetamine (MMDA) Methoxymethylenedioxymethamphetamine (MMDMA) Methylbenzodioxolylbutanamine (MBDB) Methylenedioxyamphetamine (MDA; Tenamfetamine) Methylenedioxyethylamphetamine (MDEA) Methylenedioxyhydroxyamphetamine (MDOH) Methylenedioxymethamphetamine (MDMA) Methylenedioxymethylphenethylamine (MDMPEA; Homarylamine) Methylenedioxyphenethylamine (MDPEA; Homopiperonylamine) Methylone Naphthylamphetamine (NAP) Norfenfluramine Parabromoamphetamine (PBA) Parachloroamphetamine (PCA) Parafluoroamphetamine (PFA) Parafluoromethamphetamine (PFMA) Parahydroxyamphetamine (PHA) Paraiodoamphetamine (PIA) Paramethoxyamphetamine (PMA) Paramethoxyethylamphetamine (PMEA) Paramethoxymethamphetamine (PMMA); Piperazines: 2,5-Dimethoxy-4-bromobenzylpiperazine (2C-B-BZP) Benzylpiperazine (BZP) Metachlorophenylpiperazine (mCPP) Methoxyphenylpiperazine (MeOPP; Paraperazine) Methylbenzylpiperazine (MBZP) Methylenedioxybenzylpiperazine (MDBZP; Piperonylpiperazine) Parafluorophenylpiperazine (pFPP; Fluoperazine) Trifluoromethylphenylpiperazine (TFMPP); Quinolines: PK-7059 Viqualine; Tryptamines: Alphaethyltryptamine (AET; Etryptamine) Alphamethyltryptamine (AMT; Metryptamine)

Enzyme
Inhibitors

TPH Inhibitors	AGN-2979 Fenclonine

AAAD Inhibitors	Benserazide Carbidopa

Nonselective: Iproclozide Iproniazid Isocarboxazid Nialamide Phenelzine Pheniprazine Tranylcypromine; MAO-A Selective: Befloxatone Brofaromine Cimoxatone Clorgiline Harmala Alkaloids Minaprine Moclobemide Pirlindole Toloxatone Tyrima

Others

Precursors	L-Tryptophan 5-HTP

Cofactors	Ferrous Iron (Fe²⁺) Magnesium (Mg²⁺) 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: Benzofuranylpropylaminopentane (BPAP) Phenylpropylaminopentane (PPAP); Reuptake Enhancers: Tianeptine

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