Methorphan

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Methorphan
Systematic (IUPAC) name
3-methoxy-17-methylmorphinan
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	6031-86-3^N
ATC code	?
ChemSpider	16736909^Y
UNII	8YB8F78WM1^Y
ChEMBL	CHEMBL282713^Y
Chemical data
Formula	C₁₈H₂₅NO
Mol. mass	271.40 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15?,17-,18-/m1/s1^Y Key:MKXZASYAUGDDCJ-HSFDIDPMSA-N^Y
N (what is this?) (verify)

Methorphan comes in two isomeric forms, each with differing pharmacology and effects:

Dextromethorphan - An over-the-counter cough suppressant, as well as dissociative hallucinogen.
Levomethorphan - A potent opioid analgesic that was never clinically developed.

Racemethorphan refers to the racemic mixture of both of these stereoisomers.

Dextromethorphan

[edit] See also

[edit] References

Cough and cold preparations (R05)

Althea root • Antimony pentasulfide • Creosote • Guaiacolsulfonate • Guaifenesin • Ipecacuanha (Syrup of ipecac) • Levoverbenone • Potassium iodide • Senega • Tyloxapol

Acetylcysteine • Ambroxol • Bromhexine • Carbocisteine • Domiodol • Dornase alfa • Eprazinone • Erdosteine • Letosteine • Mesna • Neltenexine • Sobrerol • Stepronin • Tiopronin

Cough suppressants

Opium alkaloids, opioids, and derivatives	Acetyldihydrocodeine • Benzylmorphine • Codeine • Dextromethorphan • Diacetylmorphine • Dihydrocodeine • Dimemorfan • Droxypropine • Ethylmorphine • Hydrocodone • Hydromorphone • Isoaminile • Laudanum • Levomethadone • Levopropoxyphene • Methadone • Nicocodeine • Nicodicodeine • Normethadone • Noscapine • Pholcodine • Thebacon • Tipepidine • Zipeprol

Other	Benzonatate • Benproperine • Bibenzonium bromide • Butamirate • Clobutinol • Clofedanol • Cloperastine • Diphenhydramine • Dibunate • Dimethoxanate • Dropropizine • Fedrilate • Glaucine • Levodropropizine • Meprotixol • Morclofone • Nepinalone • Oxolamine • Oxeladin • Pentoxyverine • Pipazetate • Prenoxdiazine • Piperidione

anat(n, x, l, c)/phys/devp

noco(c, p)/cong/tumr, sysi/epon, injr

proc, drug(R1/2/3/5/6/7)

Antihistamines
H₁R inverse agonists

First-generation	Dimenhydrinate Diphenhydramine Doxylamine Hydroxyzine Promethazine ...

Others	Amitriptyline Doxepin Mianserin Mirtazapine ...

Antipsychotics
Mixed MOA

Typicals	Chlorpromazine Haloperidol ...

Atypicals	Aripiprazole Clozapine Olanzapine Quetiapine Risperidone Ziprasidone ...

Channel blockers

Dissociatives
NMDAR antagonists

Arylcyclohexylamines	3-MeO-PCP Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine PCPr Phencyclidine Rolicyclidine Tenocyclidine Tiletamine

Morphinans	Dextromethorphan / Methorphan Dextrorphan / Morphanol

Others	Dexoxadrol Dizocilpine (MK-801) Etoxadrol Nitrous oxide Selfotel Xenon ...

Barbiturates	Amobarbital Pentobarbital Phenobarbital Secobarbital ...

Benzodiazepines	Alprazolam Chlordiazepoxide Clonazepam Diazepam Lorazepam ...

Carbamates	Carisoprodol Felbamate Meprobamate ...

GABA analogues	1,4-BD Aceburic acid GABA Gabaculine GABOB GBL GHB GHV GVL Isovaleramide Isovaleric acid Phenibut Picamilon Tiagabine Valerenic acid (Valerian) Valeric acid Valnoctamide Valproic acid (Sodium valproate / Valproate semisodium) Valpromide Vigabatrin

Neuroactive steroids	Alfaxalone Allopregnanolone Ganaxolone Tetrahydrodeoxycorticosterone ...

Nonbenzodiazepines	Eszopiclone Zaleplon Zolpidem Zopiclone ...

Piperidinediones	Glutethimide ...

Propyl phenols	Fospropofol Propofol Thymol

Quinazolinones	Methaqualone ...

Others	Baclofen Clomethiazole Diethyl ether Ethanol (Alcohol) Etomidate Gaboxadol Kavalactones (Kava Kava) Muscimol Stiripentol Theanine

Narcotics
MOR agonists

Opiates	Morphine Opium → Codeine Oripavine Thebaine

Opioids	Alfentanil Buprenorphine Butorphanol Carfentanil Diacetylmorphine (Heroin) Dihydrocodeine Ethylmorphine Etorphine Fentanyl Hydrocodone Hydromorphone Ketobemidone Levacetylmethadol Levorphanol Meperidine / Pethidine Methadone Nalbuphine Oxycodone Oxymorphone Pentazocine Phenazocine Propoxyphene Remifentanil Sufentanil Tapentadol Tramadol

Sympatholytics
α/β-AR modulators

Alpha blockers	Doxazosin Phentolamine Prazosin Tamsulosin Urapidil ...

Beta blockers	Propranolol ...

Others	Clonidine ...

Miscellaneous

Entheogens (hallucinogens)

Psychedelics
5-HT_2AR agonists

Dissociatives
NMDAR antagonists

Deliriants
mAChR antagonists

Miscellaneous

Cannabinoids CB₁R agonists	Cannabinol CP-47,497 CP-55,244 CP-55,940 DMHP HU-210 JWH-018 JWH-030 JWH-073 JWH-081 JWH-200 JWH-250 Nabilone Nabitan Nantradol Parahexyl THC (Dronabinol) WIN-55,212-2

D₂R agonists	Apomorphine Bromocriptine Cabergoline Lisuride Memantine Pergolide Piribedil Pramipexole Ropinirole Rotigotine * Also indirect D₂ agonists such as dopamine reuptake inhibitors (cocaine methylphenidate), releasing agents (amphetamine methamphetamine), and precursors (levodopa).

GABA_AR agonists	Eszopiclone Gaboxadol Ibotenic acid Muscimol Zolpidem Zopiclone

Inhalants Mixed MOA	Aliphatic hydrocarbons Butane Propane Gasoline (Petrol) Kerosene (Paraffin) Aromatic hydrocarbons Toluene Ethers Diethyl ether Enflurane Haloalkanes Chloroform Chlorofluorocarbons

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-50,488 U-69,593

σR agonists	Dextrallorphan Dextromethorphan Dextrorphan Noscapine (Narcotine)

Others	Efavirenz Glaucine Isoaminile

Analgesics (N02A, N02B)

Opioids
See also: Opioids template

Opium & alkaloids thereof	Codeine^# Morphine^# Opium Laudanum Paregoric

Semi-synthetic opium derivatives	Acetyldihydrocodeine Benzylmorphine Buprenorphine Desomorphine Dihydrocodeine Dihydromorphine Ethylmorphine Diamorphine Hydrocodone Hydromorphinol Hydromorphone Nicocodeine Nicodicodeine Nicomorphine Oxycodone Oxymorphone

Synthetic opioids	Alphaprodine Anileridine Butorphanol Dextromoramide Dextropropoxyphene Dezocine Fentanyl Ketobemidone Levorphanol Methadone Meptazinol Nalbuphine Pentazocine Propoxyphene Propiram Pethidine Phenazocine Piminodine Piritramide Tapentadol Tilidine Tramadol

Non-steroidal
anti-inflammatories
See also: NSAIDs template

Propionic acid class	Fenoprofen Flurbiprofen Ibuprofen^# Ketoprofen Naproxen Oxaprozin

Oxicam class	Meloxicam Piroxicam

Acetic acid class	Diclofenac Indometacin Ketorolac Nabumetone Sulindac Tolmetin

COX-2 inhibitors	Celecoxib Rofecoxib Valdecoxib Parecoxib Lumiracoxib

Anthranilic acid (fenamate) class	Meclofenamate Mefenamic acid

Salicylates	Aspirin (Acetylsalicylic acid)^# Benorylate Diflunisal Ethenzamide Magnesium salicylate Salicin Salicylamide Salsalate Trisalate Wintergreen (Methyl salicylate)

Atypical, adjuvant and potentiators,
Metabolic agents and miscellaneous

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

anat(n/s/m/p/4/e/b/d/c/a/f/l/g)/phys/devp

noco(m/d/e/h/v/s)/cong/tumr, sysi/epon, injr

proc, drug(N1A/2AB/C/3/4/7A/B/C/D)

Anesthetic: General anesthetics (N01A)

Ethers	Diethyl ether • Methoxypropane • Vinyl ether • halogenated ethers (Desflurane • Enflurane • Isoflurane • Methoxyflurane • Sevoflurane)

Haloalkanes	Chloroform • Halothane^# • Trichloroethylene

Others	Cyclopropane • Ethylene • Nitrous oxide^# • Xenon

Barbiturates	Hexobarbital • Methohexital • Narcobarbital • Thiopental^#

Opioids	Alfentanil • Anileridine • Fentanyl • Phenoperidine • Remifentanil • Sufentanil

Neuroactive steroids	Alfaxalone • Minaxolone

Others	Droperidol • Etomidate • Fospropofol • gamma-Hydroxybutyric acid • Ketamine^# /Esketamine • Midazolam • Propanidid • Propofol

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

anat(n/s/m/p/4/e/b/d/c/a/f/l/g)/phys/devp

noco(m/d/e/h/v/s)/cong/tumr, sysi/epon, injr

proc, drug(N1A/2AB/C/3/4/7A/B/C/D)

Receptor ligands

mAChR	Agonists: 77-LH-28-1 AC-42 AC-260,584 Aceclidine Acetylcholine AF30 AF150(S) AF267B AFDX-384 Alvameline AQRA-741 Arecoline Bethanechol Butyrylcholine Carbachol CDD-0034 CDD-0078 CDD-0097 CDD-0098 CDD-0102 Cevimeline cis-Dioxolane Ethoxysebacylcholine LY-593,039 L-689,660 LY-2,033,298 McNA343 Methacholine Milameline Muscarine NGX-267 Ocvimeline Oxotremorine PD-151,832 Pilocarpine RS86 Sabcomeline SDZ 210-086 Sebacylcholine Suberylcholine Talsaclidine Tazomeline Thiopilocarpine Vedaclidine VU-0029767 VU-0090157 VU-0152099 VU-0152100 VU-0238429 WAY-132,983 Xanomeline YM-796 Antagonists: 3-Quinuclidinyl Benzilate 4-DAMP Aclidinium Bromide Anisodamine Anisodine Atropine Atropine Methonitrate Benactyzine Benzatropine (Benztropine) Benzydamine BIBN 99 Biperiden Bornaprine CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Dimethindene Dexetimide DIBD Dicyclomine (Dicycloverine) Ditran EA-3167 EA-3443 EA-3580 EA-3834 Etanautine Etybenzatropine (Ethylbenztropine) Flavoxate Himbacine HL-031,120 Ipratropium bromide J-104,129 Hyoscyamine Mamba Toxin 3 Mamba Toxin 7 Mazaticol Mebeverine Methoctramine Metixene N-Ethyl-3-Piperidyl Benzilate N-Methyl-3-Piperidyl Benzilate Orphenadrine Otenzepad Oxybutynin PBID PD-102,807 PD-0298029 Phenglutarimide Phenyltoloxamine Pirenzepine Piroheptine Procyclidine Profenamine RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine (Hyoscine) Solifenacin Telenzepine Tiotropium bromide Tolterodine Trihexyphenidyl Tripitamine Tropatepine Tropicamide WIN-2299 Xanomeline Zamifenacin; Others: 1st Generation Antihistamines (Brompheniramine chlorphenamine cyproheptadine dimenhydrinate diphenhydramine doxylamine mepyramine/pyrilamine phenindamine pheniramine tripelennamine triprolidine, etc) Tricyclic Antidepressants (Amitriptyline doxepin trimipramine, etc) Tetracyclic Antidepressants (Amoxapine maprotiline, etc) Typical Antipsychotics (Chlorpromazine thioridazine, etc) Atypical Antipsychotics (Clozapine olanzapine quetiapine, etc)

nAChR	Agonists: 5-HIAA A-84,543 A-366,833 A-582,941 A-867,744 ABT-202 ABT-418 ABT-560 ABT-894 Acetylcholine Altinicline Anabasine Anatoxin-a AR-R17779 Butyrylcholine Carbachol Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium Epibatidine Epiboxidine Ethanol Ethoxysebacylcholine EVP-4473 EVP-6124 Galantamine GTS-21 Ispronicline Lobeline MEM-63,908 (RG-3487) Nicotine NS-1738 PHA-543,613 PHA-709,829 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A Sebacylcholine SIB-1508Y SIB-1553A SSR-180,711 Suberylcholine TC-1698 TC-1734 TC-1827 TC-2216 TC-5214 TC-5619 TC-6683 Tebanicline Tropisetron UB-165 Varenicline WAY-317,538 XY-4083 Antagonists: 18-Methoxycoronaridine α-Bungarotoxin α-Conotoxin Alcuronium Amantadine Anatruxonium Atracurium Bupropion (Amfebutamone) Chandonium Chlorisondamine Cisatracurium Coclaurine Coronaridine Dacuronium Decamethonium Dextromethorphan Dextropropoxyphene Dextrorphan Diadonium DHβE Dimethyltubocurarine (Metocurine) Dipyrandium Dizocilpine (MK-801) Doxacurium Duador Esketamine Fazadinium Gallamine Hexafluronium Hexamethonium (Benzohexonium) Ibogaine Isoflurane Ketamine Kynurenic acid Laudexium (Laudolissin) Levacetylmethadol Malouetine Mecamylamine Memantine Methadone Methorphan (Racemethorphan) Methyllycaconitine Metocurine Mivacurium Morphanol (Racemorphanol) Neramexane Nitrous Oxide Pancuronium Pempidine Pentamine Pentolinium Phencyclidine Pipecuronium Radafaxine Rapacuronium Rocuronium Surugatoxin Suxamethonium (Succinylcholine) Thiocolchicoside Toxiferine Trimethaphan Tropeinium Tubocurarine Vecuronium Xenon

Reuptake inhibitors

CHT Inhibitors	Hemicholinium-3 (Hemicholine; HC3) Triethylcholine

VAChT Inhibitors	Vesamicol

Enzyme inhibitors

ChAT inhibitors	1-(-Benzoylethyl)pyridinium 2-(α-Naphthoyl)ethyltrimethylammonium 3-Chloro-4-stillbazole 4-(1-Naphthylvinyl)pyridine Acetylseco hemicholinium-3 Acryloylcholine AF64A B115 BETA CM-54,903 N,N-Dimethylaminoethylacrylate N,N-Dimethylaminoethylchloroacetate

AChE inhibitors	Reversible: Carbamates: Aldicarb Bendiocarb Bufencarb Carbaryl Carbendazim Carbetamide Carbofuran Chlorbufam Chloropropham Ethienocarb Ethiofencarb Fenobucarb Fenoxycarb Formetanate Furadan Ladostigil Methiocarb Methomyl Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Propamocarb Propham Propoxur; Stigmines: Ganstigmine Neostigmine Phenserine Physostigmine Pyridostigmine Rivastigmine; Others: Acotiamide Ambenonium Donepezil Edrophonium Galantamine Huperzine A Minaprine Tacrine Zanapezil Irreversible: Organophosphates: Acephate Azinphos-methyl Bensulide Cadusafos Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-Methyl Coumaphos Cyclosarin (GF) Demeton Demeton-S-Methyl Diazinon Dichlorvos Dicrotophos Diisopropyl fluorophosphate (Guthion) Diisopropylphosphate Dimethoate Dioxathion Disulfoton EA-3148 Echothiophate Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fosthiazate GV Isofluorophate Isoxathion Malaoxon Malathion Methamidophos Methidathion Metrifonate Mevinphos Monocrotophos Naled Novichok agent Omethoate Oxydemeton-Methyl Paraoxon Parathion Parathion-Methyl Phorate Phosalone Phosmet Phostebupirim Phoxim Pirimiphos-Methyl Sarin (GB) Soman (GD) Tabun (GA) Temefos Terbufos Tetrachlorvinphos Tribufos Trichlorfon VE VG VM VR VX; Others: Demecarium Onchidal (Onchidella binneyi)

BChE inhibitors	Cymserine * Many of the acetylcholinesterase inhibitors listed above act as butyrylcholinesterase inhibitors.

Others

Precursors	Choline (Lecithin) Citicoline Cyprodenate Dimethylethanolamine (DMAE, deanol) Glycerophosphocholine Meclofenoxate (Centrophenoxine) Phosphatidylcholine Phosphatidylethanolamine Phosphorylcholine Pirisudanol

Cofactors	Acetic acid Acetylcarnitine Acetyl-coA Vitamin B₅ (Pantethine Pantetheine Panthenol)

Others	Acetylcholine releasing agents: α-Latrotoxin β-Bungarotoxin; Acetylcholine release inhibitors: Botulinum toxin (Botox); Acetylcholinesterase reactivators: Asoxime Obidoxime Pralidoxime

AMPA	Agonists: 5-Fluorowillardiine AMPA Domoic acid Quisqualic acid; Positive allosteric modulators: Aniracetam Cyclothiazide CX-516 CX-546 CX-614 CX-691 CX-717 Diazoxide HCTZ IDRA-21 LY-392,098 LY-404,187 LY-451,395 LY-451,646 LY-503,430 Org 26576 Oxiracetam PEPA Piracetam Pramiracetam S-18986 Sunifiram Unifiram Antagonists: ATPO Barbiturates Caroverine CNQX DNQX GYKI-52466 NBQX Perampanel Talampanel Tezampanel Topiramate; Negative allosteric modulators: GYKI-53,655

NMDA	Agonists: Glutamate/acite site competitive agonists: Aspartate Glutamate Homoquinolinic acid Ibotenic acid NMDA Quinolinic acid Tetrazolylglycine; Glycine site agonists: ACBD ACPC ACPD Alanine CCG Cycloserine DHPG Fluoroalanine Glycine HA-966 L-687,414 Milacemide Sarcosine Serine Tetrazolylglycine; Polyamine site agonists: Acamprosate Spermidine Spermine Antagonists: Competitive antagonists: AP5 (APV) AP7 CGP-37849 CGP-39551 CGP-39653 CGP-40116 CGS-19755 CPP LY-233,053 LY-235,959 LY-274,614 MDL-100,453 Midafotel (d-CPPene) NPC-12,626 NPC-17,742 PBPD PEAQX Perzinfotel PPDA SDZ-220581 Selfotel; Noncompetitive antagonists: ARR-15,896 Caroverine Dexanabinol FPL-12495 FR-115,427 Hodgkinsine Magnesium MDL-27,266 NPS-1506 Psychotridine Zinc; Uncompetitive pore blockers: 2-MDP 3-MeO-PCP 8A-PDHQ Alaproclate Amantadine Aptiganel ARL-12,495 ARL-15,896-AR ARL-16,247 Budipine Delucemine Dexoxadrol Dextrallorphan Dieticyclidine Dizocilpine Endopsychosin Esketamine Etoxadrol Eticyclidine Gacyclidine Ibogaine Indantadol Ketamine Ketobemidone Loperamide Memantine Meperidine (Pethidine) Methadone Methorphan (Dextromethorphan Levomethorphan) Methoxetamine Milnacipran Morphanol (Dextrorphan Levorphanol) NEFA Neramexane Nitrous oxide Noribogaine Orphenadrine PCPr Phencyclamine Phencyclidine Propoxyphene Remacemide Rhynchophylline Riluzole Rimantadine Rolicyclidine Sabeluzole Tenocyclidine Tiletamine Tramadol Xenon; Glycine site antagonists: ACEA-1021 ACEA-1328 ACPC Carisoprodol CGP-39653 CKA DCKA Felbamate Gavestinel GV-196,771 Kynurenic acid L-689,560 L-701,324 Lacosamide Licostinel LU-73,068 MDL-105,519 Meprobamate MRZ 2/576 PNQX ZD-9379; NR2B subunit antagonists: Besonprodil CO-101,244 (PD-174,494) CP-101,606 Eliprodil Haloperidol Ifenprodil Isoxsuprine Nylidrin Ro8-4304 Ro25-6981 Traxoprodil; Polyamine site antagonists: Arcaine Co 101676 Diaminopropane Acamprosate Diethylenetriamine Huperzine A Putrescine Ro 25-6981; Unclassified/unsorted antagonists: Chloroform Diethyl ether Enflurane Ethanol (Alcohol) Halothane Isoflurane Methoxyflurane Toluene Trichloroethane Trichloroethanol Trichloroethylene Xylene

Kainate	Agonists: 5-Iodowillardiine ATPA Domoic acid Kainic acid LY-339,434 SYM-2081 Antagonists: CNQX DNQX LY-382,884 NBQX NS102 Tezampanel Topiramate UBP-302; Negative allosteric modulators: NS-3763

Group I	Agonists: Unselective: ACPD DHPG Quisqualic acid; mGlu1-selective: Ro01-6128 Ro67-4853 Ro67-7476 VU-71; mGlu5-selective: ADX-47273 CDPPB CHPG DFB VU-1545 Antagonists: Unselective: MCPG NPS-2390; mGlu1-selective: BAY 36-7620 CPCCOEt LY-367,385 LY-456,236; mGlu5-selective: CTEP Dipraglurant DMeOB Fenobam LY-344,545 MPEP MTEP SIB-1757 SIB-1893

Group II	Agonists: Unselective: CBiPES DCG-IV Eglumegad LY-379,268 LY-404,039 LY-487,379 MGS-0028; mGlu2-selective: BINA LY-566,332 Antagonists: Unselective: APICA EGLU HYDIA LY-307,452 LY-341,495 MCPG MGS-0039: mGlu2-selective: PCCG-4; mGlu3-selective: CECXG

Group III	Agonists: Unselective: L-AP4; mGlu4-selective: PHCCC VU-001,171 VU-0155,041; mGlu7-selective: AMN082; mGlu8-selective: DCPG Antagonists: Unselective: CPPG MAP4 MSOP MPPG MTPG UBP-1112; mGlu7-selective: MMPIP

Transporter
inhibitors

EAATs	DHKA PDC WAY-213,613

vGluTs	7-CKA Evans blue

5-HT₁ receptor ligands

5-HT_1A	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 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 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 PRX-00023 Robalzotan S-15535 SB-649,915 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: Avitriptan Eletriptan Sumatriptan Zolmitriptan; Tryptamines: 5-CT 5-MT; Others: CGS-12066A 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-HT_1D	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 CP-286,601 GR-46611 L-694,247 L-772,405 PNU-109,291 PNU-142,633 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-HT_1E	Agonists: Lysergamides: Methysergide; Triptans: Eletriptan; Tryptamines: BRL-54443 Tryptamine Antagonists: Metitepine/Methiothepin

5-HT_1F	Agonists: Triptans: Eletriptan Naratriptan Sumatriptan; Tryptamines: 5-MT; Others: BRL-54443 Lasmiditan LY-334,370 Antagonists: Metitepine/Methiothepin

5-HT₂ receptor ligands


5-HT_2A	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 2C-C-NBOMe 2C-E 2C-I 2C-TFM-NBOMe 2C-T-2 2C-T-7 2C-T-21 2CBCB-NBOMe 2CBFly-NBOMe Bromo-DragonFLY DOB DOC DOI DOM MDA MDMA Mescaline 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 Dimemebfe Medifoxamine Oxaflozane PNU-22394 RH-34 Antagonists: Atypical antipsychotics: Amperozide Aripiprazole Carpipramine Clocapramine Clorotepine Clozapine Gevotroline Iloperidone Melperone Mosapramine Olanzapine Paliperidone Pimozide Quetiapine Risperidone Sertindole Ziprasidone Zotepine; Typical antipsychotics: Loxapine Pipamperone; Antidepressants: Amitriptyline Amoxapine Aptazapine Etoperidone Mianserin Mirtazapine Nefazodone Teniloxazine Trazodone; Others: 5-I-R91150 5-MeO-NBpBrT AC-90179 Adatanserin Altanserin AMDA APD-215 Blonanserin Cinanserin CSP-2503 Cyproheptadine Deramciclane Dotarizine Eplivanserin Esmirtazapine Fananserin Flibanserin 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-HT_2B	Agonists: Oxazolines: 4-Methylaminorex Aminorex; Phenethylamines: Chlorphentermine Cloforex DOB DOC DOI DOM Fenfluramine MDA MDMA Norfenfluramine; Tryptamines: 5-CT 5-MT α-Methyl-5-HT; Others: BW-723C86 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-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; 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 CP-809,101 Dimemebfe Lorcaserin Medifoxamine MK-212 Org 12,962 ORG-37,684 Oxaflozane PNU-22394 Ro60-0175 Ro60-0213 Vabicaserin WAY-629 WAY-161,503 YM-348 Antagonists: Atypical antipsychotics: Clorotepine Clozapine Iloperidone Melperone Olanzapine Paliperidone Pimozide Quetiapine Risperidone Sertindole Ziprasidone Zotepine; Typical antipsychotics: Chlorpromazine Loxapine Pipamperone; Antidepressants: Agomelatine Amitriptyline Amoxapine Aptazapine Etoperidone Fluoxetine Mianserin Mirtazapine Nefazodone Nortriptyline Tedatioxetine Trazodone; Others: Adatanserin 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	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 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 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-HT_5A	Agonists: Lysergamides: Ergotamine LSD; Tryptamines: 5-CT; Others: Valerenic Acid Antagonists: Asenapine Latrepirdine Metitepine/Methiothepin Ritanserin SB-699,551 * Note that the 5-HT_5B 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 Clorotepine Clozapine Olanzapine Risperidone Sertindole Tiospirone Ziprasidone Zotepine; Typical antipsychotics: Chlorpromazine Loxapine; Others: Butaclamol EGIS-12,233 Ketanserin LY-215,840 Metitepine/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 Vortioxetine

Reuptake inhibitors

SERT	Selective serotonin reuptake inhibitors (SSRIs): Alaproclate Citalopram Dapoxetine Desmethylcitalopram Desmethylsertraline Escitalopram Femoxetine Fluoxetine Fluvoxamine Indalpine Ifoxetine Litoxetine Lubazodone Panuramine Paroxetine Pirandamine RTI-353 Seproxetine Sertraline Tedatioxetine 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 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 Ziprasidone

VMAT	Ibogaine Reserpine Tetrabenazine

Releasing agents

Enzyme inhibitors

TPH	AGN-2979 Fenclonine

AAAD	Benserazide Carbidopa Genistein Methyldopa

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

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