Alpha-Methyltryptamine

α-Methyltryptamine

Systematic (IUPAC) name
2-(1H-indol-3-yl)-1-methyl-ethylamine
Clinical data
Legal status	Controlled (S8) (AU) Uncontrolled (CA) Legal (UK) Schedule I (US)
Routes	Oral, Insufflation, Rectal, Smoked, IM, IV[1]
Identifiers
CAS number	299-26-3 Y
ATC code	None
PubChem	CID 9287
DrugBank	DB01446
ChemSpider	8930 Y
ChEBI	CHEBI:59020 Y
ChEMBL	CHEMBL30713 Y
Synonyms	Indopan; IT-290, IT-403, U-14,164E, 3-IT[1]
Chemical data
Formula	C11H14N2
Mol. mass	174.24 g/mol
SMILES NC(CC1=CNC2=C1C=CC=C2)C
InChI InChI=1S/C11H14N2/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8,13H,6,12H2,1H3 Y Key:QSQQQURBVYWZKJ-UHFFFAOYSA-N Y
Y (what is this?)  (verify)

α-Methyltryptamine (αMT, AMT, Indopan) is a psychedelic, stimulant, and entactogen drug of the tryptamine class.^[2][3] It was originally developed as an antidepressant by workers at Upjohn in the 1960s.^[4]

Chemistry

αMT is tryptamine with a methyl substituent at the alpha carbon. Its chemical relation to tryptamine is analogous to that of amphetamine to phenethylamine, amphetamine being α-methylphenethylamine. αMT is closely related to the neurotransmitter serotonin (5-hydroxytryptamine) which partially explains its mechanism of action.

Pharmacology

αMT acts as a relatively balanced reuptake inhibitor and releasing agent of the main three monoamines; serotonin, norepinephrine, and dopamine,^[5] and as a non-selective serotonin receptor agonist.^[6]

MAOI activity

αMT has been shown as a reversible inhibitor of the enzyme monoamine oxidase (MAO) in-vitro^[7] and in-vivo.^[8]

In rats the potency of αMT as an MAO-A inhibitor in the brain was approximately equal to that of harmaline at equimolar doses.^{[note 1]} Dexamphetamine did not enhance the 5-hydroxytryptophan-induced rise of serotonin at any level.^[9]

A typical dose of harmaline for MAO inhibition is 150 mg,^[10] higher than any typical αMT dose^[11] so aMT's MAOI activity at typical doses will be significant but not total. The danger rises exponentially as αMT doses approach 150 mg due to increased monoamine release and increased MAO inhibition.

Metabolism

2-Oxo-AMT, 6-hydroxy-AMT,^[12] 7-hydroxy-AMT and 1′-hydroxy-AMT were detected as metabolites of AMT in male Wistar rats.^[13]

Dosage and effects

With 20–30 milligrams, euphoria, empathy, and psychedelic effects become apparent and can last as long as 12 hours.^[14] A dose exceeding 40 mg is generally considered as strong. In rare cases or extreme doses the duration of effects might exceed 24 hours. αMT in freebase form is reported by users to have been smoked, with doses of between and 2–5 milligrams being cited.^[1][2]

Reported side effects include anxiety, restlessness, muscle tension, jaw tightness, pupil dilation, tachycardia, headaches, nausea, and vomiting, among other effects that might commonly be attributed to LSD, psilocybin, DMT and MDMA, such as delusions and hallucinations.^[2][15]

In spite of some reported experiential similarities to MDMA, the chemicals are structurally unrelated; αMT is a tryptamine while MDMA is a phenethylamine.

Like many other serotonin releasing agents, αMT's analogue αET has been shown to produce long-lasting serotonergic neurotoxicity at very high doses.^[16] It is possible that αMT could cause the same neurotoxicity.

Legality

Australia

The 5-Methoxy analogue, 5-MeO-αMT is schedule 9 in Australia and αMT would be controlled as an analogue of this.^[17]

Sweden

Sveriges riksdags health ministry Statens folkhälsoinstitut classified αMT as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Mar 1, 2005, in their regulation SFS 2005:26 listed as alfa-metyltryptamin (AMT), making it illegal to sell or possess.^[18]

UK

It is legal in the United Kingdom, however, and does not fall under the tryptamine clause as its substituent is not on the nitrogen position. See "2001 Misuse of Drugs Act: Schedule 1, Regulation 3"^[19] for more information. Similarly, Canada has no mention of this substance in the Controlled Drugs and Substances Act.^[20]

USA

The Drug Enforcement Administration (DEA) placed MT temporarily in schedule I of the Controlled Substances Act (CSA) on April 4, 2003, pursuant to the temporary scheduling provisions of the CSA (68 FR16427). On September 29, 2004, AMT was permanently controlled as a schedule I substance under the CSA (69FR 58050).^[21]

Reported Deaths

Deaths from αMT are rare but as a powerful monoamine releaser injury can occur when excessive doses are taken or when taken with drugs such as MAOIs.^[22] Most fatalities are not verified but those which are involve excessive doses^[23] or coingestion with other drugs.^[24] A British teenager died after consuming 1 g of αMT in August 2013.^[25]

See also

Notes

References

External links

• TiHKAL entry
• αMT Entry in TiHKAL • info
• Erowid page on αMT
• Lycaeum page on αMT

v t e Entactogens Phenylalkylamines Phenethylamines: 2C-family (2C-B, 2C-I, 2C-T-2 (quasi), 2C-T-7 (quasi)) Lophophine MDMPEA MDPEA Metaescaline Amphetamines: 2-Methyl-MDA 4-FA 4-FMA 4-MTA 5-APB 5-APDB 5-APDI 5-MAPDI 5-Methyl-MDA 6-APB 6-APDB 6-APT 6-Methyl-MDA DiFMDA DMMDA DMMDA-2 EDA EDMA MDA MDDM MDEA MDIP MDMA MDMOH MDOH MDPR MMA MMDA MMDA-2 MMDMA PMA PMEA PMMA Cathinones: Brephedrone Butylone Ethylone Eutylone Flephedrone Mephedrone Methedrone Methylone Pentylone Others: 4-CAB Ariadne BDB EBDB EBDP MDMP MDPH MBDB MBDP Cyclized phenyl- alkylamines Aminoindanes: 5-IAI AMMI ETAI MDAI MDMAI MMAI TAI Aminotetralins: 6-CAT MDAT MDMAT Tryptamines 4-Methyl-αET αET αMT 5-MeO-DALT 5-MeO-DMT (quasi) DMT (quasi) 5-MeO-DiPT 5-MeO-MiPT Others Naphthylisopropylamine

v t e Hallucinogens Psychedelics 5-HT2AR agonists Lysergamides AL-LAD ALD-52 BU-LAD CYP-LAD IP-LAD Diallyllysergamide Dimethyllysergamide Ergometrine ETH-LAD LAE-32 LPD-824 LSA LSD LSD-Pip LSH LSM-775 Lysergic acid 2-butyl amide LSZ Lysergic acid 3-pentyl amide Methylergometrine Methylisopropyllysergamide Methysergide N1-Methyl-lysergic acid diethylamide PARGY-LAD PRO-LAD Phenethylamines Aleph 2-Methyl-MDA 2C-B 2C-B-Dragonfly 2C-B-FLY βk-2C-B 2C-C 2C-C-FLY 25C-NBOMe 25CN-NBOH 25CN-NBOMe 25D-NBOMe 2C-D 2C-D-FLY 2C-E 2C-E-FLY 2C-E-NBOMe 2C-EF 2C-F 2C-F-NBOMe 2C-G 2C-G-NBOMe 2C-H-NBOMe 2C-I 2C-I-FLY 2C-N 25N-NBOMe 2C-O 2C-O-4 2C-P 2C-T 2C-T-2 2C-T-4 2C-T-4-NBOMe 2C-T-7 2C-T-7-FLY 2C-T-7-NBOH 2C-T-8 2C-T-13 2C-T-15 2C-T-17 2C-T-19 2C-T-21 2C-TFM 25TFM-NBOMe 2C-YN 2CBCB-NBOMe 2CBFly-NBOMe 2CD-5EtO 25B-NBOMe 25C-NBOH 25I-NBMD 25I-NBOH 25I-NBOMe 2C-P-NBOMe 3C-AL 3C-E 3C-P 5-APB 5-APDB 5-APDI 5-Methyl-MDA 6-APB 6-APDB 6-Methyl-MDA Br-DFLY DESOXY DMMDA DMMDA-2 DOB DOB-FLY DOC DOEF DOET DOF DOI DOM DOM-FLY DON DOPR DOTFM Escaline Ganesha HOT-2 HOT-7 HOT-17 Isoproscaline Jimscaline Juncosamine Lophophine Macromerine MDA MDEA MDMA Mescaline Methallylescaline MMA MMDA MMDA-2 MMDA-3a MMDMA NBOMe-mescaline Proscaline TCB-2 TFMFly TMA Piperazines pFPP TMFPP mCPP Tryptamines 1-Methyl-5-methoxy-diisopropyltryptamine 2,N,N-TMT 4,5-DHP-AMT 4,5-DHP-DMT 4-Acetoxy-DALT 4-Acetoxy-DET 4-Acetoxy-DiPT 4-Acetoxy-DMT 4-Acetoxy-DPT 4-Acetoxy-MiPT 4-HO-5-MeO-DMT 4-HO-DBT 4-HO-DPT 4-HO-MET 4-HO-MPMI 4-HO-MPT 4,N,N-TMT 4-Propionyloxy-DMT 5,6-diBr-DMT 5-AcO-DMT 5-Bromo-DMT 5-Me-MIPT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 5-MeO-α,N,N-TMT 5-MeO-α-ET 5-MeO-α-MT 5-MeO-DALT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT 5-MeO-DPT 5-MeO-EiPT 5-MeO-MET 5-MeO-MiPT 5-MeO-MPMI 5-N,N-TMT 7,N,N-TMT α-ET α-MT α,N,N-TMT Aeruginascin Baeocystin Bufotenin DALT DBT DCPT DET DIPT DMT DPT EiPT Ethocin Ethocybin Iprocin MET Miprocin MiPT Norbaeocystin PiPT Psilocin Psilocybin Others AL-38022A Elemicin Ibogaine Myristicin Noribogaine Voacangine Dissociatives NMDAR antagonists Adamantanes Amantadine Memantine Rimantadine Arylcyclohexylamines 3-MeO-PCP 4-MeO-PCP Dieticyclidine Diphenidine Esketamine Ethketamine Eticyclidine Gacyclidine Ketamine Methoxetamine Methoxyketamine Neramexane PCPr Phencyclidine Rolicyclidine Tenocyclidine Tiletamine Morphinans Dextrallorphan Dextromethorphan Dextrorphan Racemethorphan Racemorphan Others 2-MDP 8A-PDHQ Aptiganel Dexoxadrol Dizocilpine Etoxadrol Ibogaine Midafotel NEFA Nitrous oxide Noribogaine Perzinfotel Remacemide Selfotel Xenon Deliriants mAChR antagonists 3-Quinuclidinyl benzilate Atropine Benactyzine Benzatropine Benzydamine Biperiden BRN-1484501 Brompheniramine CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Chloropyramine Chlorphenamine Clemastine CS-27349 Cyclizine Cyproheptadine Dicycloverine Dimenhydrinate Diphenhydramine Ditran Doxylamine EA-3167 EA-3443 EA-3580 EA-3834 Flavoxate Hyoscyamine Meclozine Mepyramine N-Ethyl-3-piperidyl benzilate N-Methyl-3-piperidyl benzilate Orphenadrine Oxybutynin Pheniramine Phenyltoloxamine Procyclidine Promethazine Scopolamine Tolterodine Trihexyphenidyl Tripelennamine Triprolidine WIN-2299 Miscellaneous Cannabinoids CB1R agonists Phytocannabinoids Cannabinol THC (Dronabinol) THCV (Cannabidiol has different mechanism of action) Synthetic CP 47,497 CP 55,244 CP 55,940 DMHP HU-210 JWH-018 JWH-030 JWH-073 JWH-081 JWH-200 JWH-250 Levonantradol Nabilone Nabitan Parahexyl WIN 55,212-2 D2R agonists Aporphine Bromocriptine Cabergoline Lisuride Memantine Nuciferine Pergolide Piribedil Pramipexole Ropinirole Rotigotine Also indirect D2 agonists, such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa). GABAAR agonists Eszopiclone Gaboxadol Ibotenic acid Muscimol Zaleplon Zolpidem Zopiclone Inhalants Mixed MOA Aliphatic hydrocarbons Butane Gasoline Kerosene Propane Aromatic hydrocarbons Toluene Ethers Diethyl ether Enflurane Haloalkanes Chlorofluorocarbons Chloroform κOR agonists 2-EMSB 2-MMSB Alazocine Bremazocine Butorphanol Cyclazocine Cyprenorphine Dextrallorphan Dezocine Enadoline Herkinorin HZ-2 Ibogaine Ketazocine LPK-26 Metazocine Nalbuphine Nalorphine Noribogaine Pentazocine Phenazocine Salvinorin A Spiradoline Tifluadom U-50488 U-69,593 MAO inhibitors Harmaline Harmine Tetrahydroharmine Yohimbine σR agonists DMT Dextrallorphan Dextromethorphan Dextrorphan Noscapine Others Efavirenz Glaucine Isoaminile Pukateine

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 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 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-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 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 Furfenorex Gepefrine Hexapradol HMMA Hordenine 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 N-Benzyl-1-phenethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine 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 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 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 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

v t e 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 Xamoterol Zilpaterol Zinterol Antagonists: Acebutolol Adaprolol Adimolol Afurolol Alprenolol Alprenoxime Amosulalol Ancarolol Arnolol Arotinolol Atenolol Befunolol Betaxolol Bevantolol Bisoprolol Bopindolol Bormetolol Bornaprolol Brefonalol Bucindolol Bucumolol Bufetolol Buftiralol Bufuralol Bunitrolol Bunolol Bupranolol Burocrolol Butaxamine Butidrine Butofilolol Capsinolol Carazolol Carpindolol Carteolol Carvedilol Celiprolol Cetamolol Cicloprolol Cinamolol Cloranolol Cyanopindolol Dalbraminol Dexpropranolol Diacetolol Dichloroisoprenaline Dihydroalprenolol Dilevalol Diprafenone Draquinolol Dropranolol Ecastolol Epanolol Ericolol Ersentilide Esatenolol Esmolol 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 Terthianolol 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 (Amfebutamone) Fencamine Fencamfamine 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 Methylnaphthidate Naphyrone NS-2359 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 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 Butylone Cathine Cathinone Clobenzorex Clortermine Dimethylamphetamine Dimethylcathinone DMA DMMA EBDB Ephedrine Ethcathinone Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine Hydroxyamphetamine IAP IMP Iofetamine Lisdexamfetamine Lophophine MBDB MDA MDEA MDMA MDMPEA MDOH MDPEA Mefenorex Mephedrone Mephentermine Methamphetamine (Dextromethamphetamine Levomethamphetamine) Methcathinone Methedrone Methylone 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

v t e 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   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 LR-5182 Manifaxine Mazindol Medifoxamine Mesocarb Modafinil Nefopam Nomifensine NS-2359 O-2172 Pridefrine Propylamphetamine 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 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 Butylone Cathine Cathinone Clobenzorex Clortermine D-Deprenyl DMA DMMA Dimethylamphetamine Dimethylcathinone Ephedrine Ethcathinone EBDB Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine Hydroxyamphetamine Iofetamine Lophophine Mefenorex Mephedrone Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methcathinone Methedrone MMDA MMDMA MBDB MDA MDEA MDMA MDMPEA MDOH MDPEA Methylone 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 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

v t e Serotonergics   5-HT1 receptor ligands 5-HT1A Agonists: Azapirones: Alnespirone Binospirone Buspirone Enilospirone Eptapirone Gepirone Ipsapirone Perospirone Revospirone Tandospirone Tiospirone Umespirone Zalospirone; Antidepressants: Etoperidone Nefazodone Trazodone Vortioxetine; Antipsychotics: Aripiprazole Asenapine Clozapine Quetiapine Ziprasidone; Ergolines: Dihydroergotamine Bromocriptine Ergotamine Lisuride Methysergide LSD; Tryptamines: 5-CT 5-MeO-DMT 5-MT Bufotenin DMT Indorenate Psilocin Psilocybin; Others: 8-OH-DPAT Adatanserin Bay R 1531 Befiradol BMY-14802 Cannabidiol Dimemebfe Ebalzotan Eltoprazine F-11,461 F-12,826 F-13,714 F-14,679 F-15,063 F-15,599 Flesinoxan Flibanserin Lesopitron LY-293,284 LY-301,317 MKC-242 Naluzotan NBUMP Osemozotan Oxaflozane Pardoprunox Piclozotan Rauwolscine Repinotan Roxindole RU-24,969 S 14,506 S-14,671 S-15,535 Sarizotan SSR-181,507 Sunepitron U-92,016-A Urapidil Vilazodone Xaliproden Yohimbine Antagonists: Antipsychotics: Iloperidone Risperidone Sertindole; Beta blockers: Alprenolol Cyanopindolol Iodocyanopindolol Oxprenolol Pindobind Pindolol Propranolol Tertatolol; Others: AV965 BMY-7,378 CSP-2503 Dotarizine Flopropione GR-46611 Isamoltane Lecozotan Mefway Metitepine/Methiothepin MPPF NAN-190 Robalzotan S-15535 SB-649,915 SDZ 216-525 Spiperone Spiramide Spiroxatrine UH-301 WAY-100,135 WAY-100,635 Xylamidine 5-HT1B Agonists: Lysergamides: Dihydroergotamine Ergotamine Methysergide; Piperazines: Eltoprazine TFMPP; Triptans: Avitriptan Eletriptan Sumatriptan Zolmitriptan; Tryptamines: 5-CT 5-MT; Others: CGS-12066A Bromocriptine CP-93,129 CP-94,253 CP-135,807 RU-24,969 Vortioxetine Antagonists: Lysergamides: Metergoline; Others: AR-A000002 Elzasonan GR-127,935 Isamoltane Metitepine/Methiothepin SB-216,641 SB-224,289 SB-236,057 Yohimbine 5-HT1D Agonists: Lysergamides: Dihydroergotamine Methysergide; Triptans: Almotriptan Avitriptan Eletriptan Frovatriptan Naratriptan Rizatriptan Sumatriptan Zolmitriptan; Tryptamines: 5-CT 5-Ethyl-DMT 5-MT 5-(Nonyloxy)tryptamine; Others: CP-135,807 Bromocriptine CP-286,601 GR-46611 L-694,247 L-772,405 PNU-109,291 PNU-142633 Antagonists: Lysergamides: Metergoline; Others: Alniditan BRL-15,572 Elzasonan GR-127,935 Ketanserin LY-310,762 LY-367,642 LY-456,219 LY-456,220 Metitepine/Methiothepin Ritanserin Yohimbine Ziprasidone 5-HT1E Agonists: Lysergamides: Methysergide; Triptans: Eletriptan; Tryptamines: BRL-54443 Tryptamine Antagonists: Metitepine/Methiothepin 5-HT1F Agonists: Triptans: Eletriptan Naratriptan Sumatriptan; Tryptamines: 5-MT; Others: BRL-54443 Bromocriptine Lasmiditan LY-334,370 Antagonists: Metitepine/Methiothepin   5-HT2 receptor ligands 5-HT2A Agonists: Lysergamides: ALD-52 Ergometrine Lisuride LA-SS-Az LSD LSD-Pip Lysergic acid 2-butyl amide Lysergic acid 3-pentyl amide Methysergide; Phenethylamines: 25I-NBF 25I-NBMD 25I-NBOH 25I-NBOMe 2C-B 2C-B-FLY 2CB-Ind 25B-NBOMe 25C-NBOMe 2C-E 2C-I 25TFM-NBOMe 2C-T-2 2C-T-7 2C-T-21 2CBCB-NBOMe 2CBFly-NBOMe Juncosamine Bromo-DragonFLY DOB DOC DOI DOM MDA MDMA Mescaline 25CN-NBOH TCB-2 TFMFly; Piperazines: BZP Quipazine TFMPP; Tryptamines: 5-CT 5-MeO-α-ET 5-MeO-α-MT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT 5-MeO-DPT 5-MT α-ET α-Methyl-5-HT α-MT Bufotenin DET DiPT DMT DPT Psilocin Psilocybin; Others: AL-34662 AL-37350A Bromocriptine Dimemebfe Medifoxamine O-4310 Oxaflozane PHA-57378 PNU-22394 PNU-181731 RH-34 Antagonists: Atypical antipsychotics: Amperozide Aripiprazole Blonanserin Carpipramine Clocapramine Clorotepine Clozapine Gevotroline Iloperidone Melperone Mosapramine Olanzapine Paliperidone Quetiapine Risperidone Sertindole Zicronapine Ziprasidone Zotepine; Typical antipsychotics: Loxapine Pipamperone; Antidepressants: Amitriptyline Amoxapine Aptazapine Etoperidone Mianserin Mirtazapine Nefazodone Pimozide Teniloxazine Trazodone; Others: 5-I-R91150 5-MeO-NBpBrT AC-90179 Adatanserin Altanserin AMDA APD-215 Cinanserin CSP-2503 Cyproheptadine Deramciclane Dotarizine Eplivanserin Esmirtazapine Fananserin Flibanserin Glemanserin Ketanserin KML-010 Lubazodone Mepiprazole Metitepine/Methiothepin Nantenine Pimavanserin Pizotifen Pruvanserin Rauwolscine Ritanserin S-14,671 Sarpogrelate Setoperone Spiperone Spiramide SR-46349B Volinanserin Xylamidine Yohimbine 5-HT2B Agonists: Oxazolines: 4-Methylaminorex Aminorex; Phenethylamines: Chlorphentermine Cloforex DOB DOC DOI DOM Fenfluramine (Dexfenfluramine, Levofenfluramine) MDA MDMA Norfenfluramine; Tryptamines: 5-CT 5-MT α-Methyl-5-HT; Others: BW-723C86 Bromocriptine Cabergoline mCPP Pergolide PNU-22394 Ro60-0175 Antagonists: Agomelatine Asenapine EGIS-7625 Ketanserin Lisuride LY-272,015 Metitepine/Methiothepin PRX-08066 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-HT2C Agonists: Phenethylamines: 2C-B 2C-E 2C-I 2C-T-2 2C-T-7 2C-T-21 DOB DOC DOI DOM MDA MDMA Mescaline; Piperazines: Aripiprazole mCPP TFMPP; Tryptamines: 5-CT 5-MeO-α-ET 5-MeO-α-MT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT 5-MeO-DPT 5-MT α-ET α-Methyl-5-HT α-MT Bufotenin DET DiPT DMT DPT Psilocin Psilocybin; Others: A-372,159 AL-38022A Alstonine Bromocriptine CP-809,101 Dimemebfe Lorcaserin Medifoxamine MK-212 Org 12,962 ORG-37,684 Oxaflozane PHA-57378 PNU-22394 PNU-181731 Ro60-0175 Ro60-0213 Vabicaserin WAY-629 WAY-161,503 YM-348 Antagonists: Atypical antipsychotics: Clorotepine Clozapine Iloperidone Melperone Olanzapine Paliperidone Quetiapine Risperidone Sertindole Ziprasidone Zotepine; Typical antipsychotics: Chlorpromazine Loxapine Pimozide Pipamperone; Antidepressants: Agomelatine Amitriptyline Amoxapine Aptazapine Etoperidone Fluoxetine Mianserin Mirtazapine Nefazodone Nortriptyline Tedatioxetine Trazodone; Others: Adatanserin CEPC Cinanserin Cyproheptadine Deramciclane Dotarizine Eltoprazine Esmirtazapine FR-260,010 Ketanserin Ketotifen Latrepirdine Metitepine/Methiothepin Methysergide Pizotifen Ritanserin RS-102,221 S-14,671 SB-200,646 SB-206,553 SB-221,284 SB-228,357 SB-242,084 SB-243,213 SDZ SER-082 Xylamidine   5-HT3 5-HT4 5-HT5 5-HT6 5-HT7 ligands 5-HT3 Agonists: Piperazines: BZP Quipazine; Tryptamines: 2-Methyl-5-HT 5-CT; Others: Chlorophenylbiguanide Butanol Ethanol Halothane Isoflurane RS-56812 SR-57,227 SR-57,227-A Toluene Trichloroethane Trichloroethanol Trichloroethylene YM-31636 Antagonists: Antiemetics: AS-8112 Alosetron Azasetron Batanopride Bemesetron Cilansetron Dazopride Dolasetron Galanolactone Granisetron Lerisetron Ondansetron Palonosetron Ramosetron Renzapride Tropisetron Zacopride Zatosetron; Atypical antipsychotics: Clozapine Olanzapine Quetiapine; Tetracyclic antidepressants: Amoxapine Mianserin Mirtazapine; Others: CSP-2503 ICS-205,930 MDL-72,222 Memantine Nitrous Oxide Ricasetron Sevoflurane Tedatioxetine Thujone Tropanserin Vortioxetine Xenon 5-HT4 Agonists: Gastroprokinetic Agents: Cinitapride Cisapride Dazopride Metoclopramide Mosapride Prucalopride Renzapride Tegaserod Velusetrag Zacopride; Others: 5-MT BIMU8 CJ-033,466 PRX-03140 RS-67333 RS-67506 SL65.0155 Antagonists: GR-113,808 GR-125,487 L-Lysine Piboserod RS-39604 RS-67532 SB-203,186 SB-204,070 5-HT5A Agonists: Lysergamides: Ergotamine LSD; Tryptamines: 5-CT; Others: Valerenic Acid Antagonists: Asenapine Latrepirdine Metitepine/Methiothepin Ritanserin SB-699,551 * Note that the 5-HT5B receptor is not functional in humans. 5-HT6 Agonists: Lysergamides: Dihydroergotamine Ergotamine Lisuride LSD Mesulergine Metergoline Methysergide; Tryptamines: 2-Methyl-5-HT 5-BT 5-CT 5-MT Bufotenin E-6801 E-6837 EMD-386,088 EMDT LY-586,713 N-Methyl-5-HT Tryptamine; Others: WAY-181,187 WAY-208,466 Antagonists: Antidepressants: Amitriptyline Amoxapine Clomipramine Doxepin Mianserin Nortriptyline; Atypical antipsychotics: Aripiprazole Asenapine Clorotepine Clozapine Fluperlapine Iloperidone Olanzapine Tiospirone; Typical antipsychotics: Chlorpromazine Loxapine; Others: BGC20-760 BVT-5182 BVT-74316 Cerlapirdine EGIS-12,233 GW-742,457 Ketanserin Latrepirdine Lu AE58054 Metitepine/Methiothepin MS-245 PRX-07034 Ritanserin Ro04-6790 Ro 63-0563 SB-258,585 SB-271,046 SB-357,134 SB-399,885 SB-742,457 5-HT7 Agonists: Lysergamides: LSD; Tryptamines: 5-CT 5-MT Bufotenin; Others: 8-OH-DPAT AS-19 Bifeprunox E-55888 LP-12 LP-44 RU-24,969 Sarizotan Antagonists: Lysergamides: 2-Bromo-LSD Bromocriptine Dihydroergotamine Ergotamine Mesulergine Metergoline Methysergide; Antidepressants: Amitriptyline Amoxapine Clomipramine Imipramine Maprotiline Mianserin; Atypical antipsychotics: Amisulpride Aripiprazole Asenapine Clorotepine Clozapine Olanzapine Risperidone Sertindole Tiospirone Ziprasidone Zotepine; Typical antipsychotics: Chlorpromazine Loxapine; Pimozide; Others: Butaclamol EGIS-12,233 Ketanserin LY-215,840 Metitepine/Methiothepin 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 Vortioxetine   Reuptake inhibitors SERT Selective serotonin reuptake inhibitors (SSRIs): Alaproclate Citalopram Dapoxetine Desmethylcitalopram Desmethylsertraline Escitalopram Femoxetine Fluoxetine Fluvoxamine Indalpine Ifoxetine Litoxetine Lubazodone Omiloxetine Panuramine Paroxetine Pirandamine RTI-353 Seproxetine Sertraline Vilazodone Vortioxetine Zimelidine; Serotonin-norepinephrine reuptake inhibitors (SNRIs): Bicifadine Desvenlafaxine Duloxetine Eclanamine Levomilnacipran Milnacipran Sibutramine Venlafaxine; Serotonin-norepinephrine-dopamine reuptake inhibitors (SNDRIs): Brasofensine Diclofensine DOV-102,677 DOV-21,947 DOV-216,303 NS-2359 SEP-225289 SEP-227,162 Tedatioxetine Tesofensine; Tricyclic antidepressants (TCAs): Amitriptyline Butriptyline Cianopramine Clomipramine Desipramine Dosulepin Doxepin Imipramine Lofepramine Nortriptyline Pipofezine Protriptyline Trimipramine; Tetracyclic antidepressants (TeCAs): Amoxapine; Piperazines: Nefazodone Trazodone; Antihistamines: Brompheniramine Chlorphenamine Diphenhydramine Mepyramine/Pyrilamine Pheniramine Tripelennamine; Opioids: Pethidine Methadone Propoxyphene; Others: Cocaine CP-39,332 Cyclobenzaprine Dextromethorphan Dextrorphan EXP-561 Fezolamine Mesembrine Nefopam PIM-35 Pridefine Roxindole SB-649,915 Tofenacin Ziprasidone VMAT Ibogaine Reserpine Tetrabenazine   Releasing agents Aminoindanes: 5-IAI AMMI ETAI MDAI MDMAI MMAI TAI; Aminotetralins: 6-CAT 8-OH-DPAT MDAT MDMAT; Oxazolines: 4-Methylaminorex Aminorex Clominorex Fluminorex; Phenethylamines (also Amphetamines, Cathinones, Phentermines, etc): 2-Methyl-MDA 4-CAB 4-FA 4-FMA 4-HA 4-MTA 5-APDB 5-Methyl-MDA 6-APDB 6-Methyl-MDA AEMMA Amiflamine BDB BOH Brephedrone Butylone Chlorphentermine Cloforex Amfepramone Metamfepramone DCA DFMDA DMA DMMA EBDB EDMA Ethylone Etolorex Fenfluramine (Dexfenfluramine, Levofenfluramine) Flephedrone IAP IMP Iofetamine Lophophine MBDB MDA MDEA MDHMA MDMA MDMPEA MDOH MDPEA Mephedrone Methedrone Methylone MMA MMDA MMDMA MMMA NAP Norfenfluramine 4-TFMA pBA pCA pIA PMA PMEA PMMA TAP; Piperazines: 2C-B-BZP 3-MeOPP BZP DCPP MBZP mCPP MDBZP MeOPP Mepiprazole pCPP pFPP pTFMPP TFMPP; Tryptamines: 4-Methyl-αET 4-Methyl-αMT 5-CT 5-MeO-αET 5-MeO-αMT 5-MT αET αMT DMT Tryptamine (itself); Others: Indeloxazine Tramadol Viqualine   Enzyme inhibitors Anabolism TPH AGN-2979 Fenclonine AAAD Benserazide Carbidopa Genistein Methyldopa 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   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: BPAP * PPAP; Reuptake enhancers: Tianeptine; Steroids: Anabolic-androgenic steroids

v t e Tryptamines 2-Methyl-5-HT 4,5-DHP-DMT 4,5-MDO-DMT 4,5-MDO-DiPT 4-AcO-DALT 4-AcO-DET 4-AcO-DMT 4-AcO-DiPT 4-AcO-NMT 4-AcO-MET 4-AcO-DPT 4-AcO-MiPT 4-HO-DALT 4-HO-DET 4-HO-DiPT 4-HO-DSBT 4-HO-MET 4-HO-MiPT 4-HO-NMT 4-HO-αMT 4-Me-αET 4-Me-αMT 4-MeO-DiPT 4-MeO-DMT 5-BT 5-Bromo-DMT 5-CT 5-Ethoxy-αMT 5-Fluoro-αMT 5-HO-αMT 5-HO-DiPT 5-HTP 5-Ethoxy-DMT 5-Ethyl-DMT 5-Fluoro-DMT 5-Methyl-DMT 5-Methoxytryptamine 5-MeO-7,N,N-TMT 5-Methyl-αET 5-MeO-αET 5-MeO-αMT 5-MeO-DALT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT 5-MeO-DPT 5-MeO-MALT 5-MeO-MiPT 5-MeO-NBpBrT 5,7-Dihydroxytryptamine 5-(Nonyloxy)tryptamine 6-Fluoro-αMT 7-Methyl-αET 7-Methyl-DMT αET αMT Aeruginascin AL-37350A BW-723C86 Baeocystin Bufotenidine Bufotenin (5-HO-DMT) DALT Desformylflustrabromine DET DiPT DMT DPT Ethocybin EiPT EMDT EPT Ethocin FGIN-127 FGIN-143 Ibogaine Indorenate Iprocin MET MiPT MPT Miprocin Melatonin MS-245 NAS NMT Norbaeocystin Normelatonin O-4310 Oxypertine PiPT Psilocin (4-HO-DMT) Psilocybin (4-PO-DMT) Rizatriptan Serotonin ST-1936 Sumatriptan Tryptamine Tryptophan Yohimbine Yuremamine Zolmitriptan