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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

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 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

Ampyrone/Aminophenazone • Metamizole • Phenazone • Propyphenazone

Ajulemic acid • AM404 • Cannabidiol • Cannabis • Nabilone • Nabiximols • Tetrahydrocannabinol

Paracetamol (acetaminophen)^# • Phenacetin • Propacetamol

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

Amitryptiline • Befiradol • Bicifadine • Carisoprodol • Camphor • Cimetidine • Clonidine • Chlorzoxazone • Cyclobenzaprine • Duloxetine • Esreboxetine • Flupirtine • Gabapentin • Glafenine • Hydroxyzine • Ketamine • Menthol • Mephenoxalone • Methocarbamol • Nefopam • Orphenadrine • Pregabalin • Proglumide • Scopolamine • Tebanicline • Trazodone • Gabapentin enacarbil • Ziconotide

^#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, 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 • 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

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) • Flephedrone • IAP • IMP • 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 • 2-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

TPH	AGN-2979 • Fenclonine

AAAD	Benserazide • Carbidopa • Genistein • Methyldopa

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 • Befol • Brofaromine • Cimoxatone • Clorgiline • 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

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