Neramexane

Neramexane
Systematic (IUPAC) name

1,3,3,5,5-pentamethylcyclohexanamine
Clinical data
Legal status	?
Identifiers
CAS number	^Y
ATC code	None
PubChem
ChemSpider
UNII	^Y
Chemical data
Formula	C₁₁H₂₃N
Mol. mass	169.307 g/mol
SMILES CC1(CC(CC(C1)(C)N)(C)C)C
InChI InChI=1S/C11H23N/c1-9(2)6-10(3,4)8-11(5,12)7-9/h6-8,12H2,1-5H3 Key:OGZQTTHDGQBLBT-UHFFFAOYSA-N
Y

Neramexane is a drug related to memantine,^[1] which acts as an NMDA antagonist^[2] and has neuroprotective effects.^[3] It is being developed for various possible applications, including treatment of tinnitus,^[4]^[5] Alzheimer's disease,^[6] drug addiction^[7] and as an analgesic.^[8] Animal studies have also suggested antidepressant^[9] and nootropic^[10] actions, so there are a wide range of potential applications this drug may be used for. It also acts as a nicotinic acetylcholine receptor antagonist.^[11]

References

^ Gilling K, Jatzke C, Wollenburg C, Vanejevs M, Kauss V, Jirgensons A, Parsons CG. A novel class of amino-alkylcyclohexanes as uncompetitive, fast, voltage-dependent, N-methyl-D-aspartate (NMDA) receptor antagonists--in vitro characterization. Journal of Neural Transmission. 2007;114(12):1529-37. PMID 17728997
^ Danysz W, Parsons CG, Jirgensons A, Kauss V, Tillner J. Amino-alkyl-cyclohexanes as a novel class of uncompetitive NMDA receptor antagonists. Current Pharmaceutical Design. 2002;8(10):835-43. PMID 11945134
^ Danysz W, Parsons CG. Neuroprotective potential of ionotropic glutamate receptor antagonists. Neurotoxicity Research. 2002 Mar;4(2):119-26. PMID 12829411
^ ClinicalTrials.gov NCT00405886 Neramexane for Tinnitus
^ ClinicalTrials.gov NCT00739635 Efficacy, Safety and Tolerability of Neramexane in Patients With Subjective Tinnitus
^ Rammes G, Schierloh A. Neramexane (merz pharmaceuticals/forest laboratories). IDrugs. 2006 Feb;9(2):128-35. PMID 16523403
^ Kotlinska J, Biala G, Rafalski P, Bochenski M, Danysz W. Effect of neramexane on ethanol dependence and reinforcement. European Journal of Pharmacology. 2004 Oct 25;503(1-3):95-8. PMID 15496302
^ Klein T, Magerl W, Hanschmann A, Althaus M, Treede RD. Antihyperalgesic and analgesic properties of the N-methyl-D-aspartate (NMDA) receptor antagonist neramexane in a human surrogate model of neurogenic hyperalgesia. European Journal of Pain. 2008 Jan;12(1):17-29. PMID 17449306
^ Kos T, Legutko B, Danysz W, Samoriski G, Popik P. Enhancement of antidepressant-like effects but not brain-derived neurotrophic factor mRNA expression by the novel N-methyl-D-aspartate receptor antagonist neramexane in mice. Journal of Pharmacology and Experimental Therapeutics. 2006 Sep;318(3):1128-36. PMID 16740621
^ Zoladz PR, Campbell AM, Park CR, Schaefer D, Danysz W, Diamond DM. Enhancement of long-term spatial memory in adult rats by the noncompetitive NMDA receptor antagonists, memantine and neramexane. Pharmacology, Biochemistry and Behaviour. 2006 Oct;85(2):298-306. Epub 2006 Oct 11. PMID 17045636
^ Plazas PV, Savino J, Kracun S, et al. (July 2007). "Inhibition of the alpha9alpha10 nicotinic cholinergic receptor by neramexane, an open channel blocker of N-methyl-D-aspartate receptors" 566 (1-3). pp. 11–9.

Hypnotics/sedatives (N05C)

GABA_A
agonists/PAMs

Alcohols:	2M2B Chloralodol Ethanol Alcohol Ethchlorvynol Methylpentynol Trichloroethanol

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

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

Carbamates:	Carisoprodol Emylcamate Ethinamate Hexapropymate Meprobamate Methocarbamol Phenprobamate Procymate Tybamate

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

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

Phenols:	Fospropofol Propofol

Piperidinediones:	Glutethimide Methyprylon Pyrithyldione Piperidione

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

Volatiles/gases	Acetophenone Acetylglycinamide chloral hydrate Centalun Chloral hydrate Paraldehyde

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

GABA_B
agonists

H₁ inverse
agonists

Antihistamines:	Captodiame Cyproheptadine Diphenhydramine Doxylamine Hydroxyzine Methapyrilene Pheniramine Promethazine Propiomazine

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

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

α₁-Adrenergic
antagonists

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

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

Others:	Niaprazine

α₂-Adrenergic
agonists

5-HT_2A
antagonists

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

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

Others:	Eplivanserin Niaprazine Pruvanserin Volinanserin

Melatonin
agonists

Orexin
antagonists

Others

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

Hallucinogens

Psychedelics
5-HT_2AR agonists

Lysergamides	AL-LAD ALD-52 BU-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-(2,5-Dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine 2-Methyl-MDA 2C-B 2C-B-Dragonfly 2C-B-FLY 2CB-Ind 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 25E-NBOMe 2C-EF 2C-F 25F-NBOMe 2C-G 25G-NBOMe 25H-NBOMe 2C-I 2C-IP 2C-I-FLY 2C-N 25N-NBOMe 2C-O 2C-O-4 2C-P 2C-T 2C-T-2 2C-T-4 25T4-NBOMe 2C-T-7 2C-T-7-FLY 25T7-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 2C-V 2CBCB-NBOMe 2CBFly-NBOMe 2CD-5EtO 25B-NBOMe 25B-NBOH 25C-NBOH 25I-NBMD 25I-NBOH 25I-NBF 25I-NBOMe 25P-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 BOB BOD Escaline Ganesha HOT-2 HOT-7 HOT-17 Isoproscaline Jimscaline 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 Ibogaine Iprocin MET Miprocin MiPT Norbaeocystin Noribogaine PiPT Psilocin Psilocybin Voacangine

Others	AL-38022A ALPHA Dimemebfe Efavirenz Elemicin M-ALPHA Myristicin RH-34

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

Miscellaneous

Cannabinoids
CB₁R agonists

Phytocannabinoids	Cannabinol THC (Dronabinol) THCV (Cannabidiol has different mechanism of action)

Synthetic	4-HTMPIPO 5F-PB-22 AB-001 AB-005 A-836,339 AB-CHMINACA AB-FUBINACA AB-PINACA ADB-FUBINACA ADB-PINACA ADBICA AM-630 AM-679 AM-694 AM-1220 AM-1221 AM-1235 AM-1241 AM-1248 AM-2201 AM-2232 AM-2233 APICA APINACA CB-13 CP 47,497 CP 55,244 CP 55,940 DMHP HU-210 HU-308 JWH-007 JWH-015 JWH-018 JWH-019 JWH-030 JWH-073 JWH-081 JWH-098 JWH-116 JWH-122 JWH-149 JWH-167 JWH-182 JWH-193 JWH-198 JWH-200 JWH-203 JWH-210 JWH-250 JWH-251 JWH-398 JWH-424 JTE 7-31 JTE-907 Levonantradol MAM-2201 MDA-19 MN-25 NESS-0327 NESS-040C5 Nabilone Nabitan Org 28611 Parahexyl QUCHIC QUPIC RCS-4 RCS-8 SDB-006 STS-135 THC-O-acetate THC-O-phosphate UR-144 WIN 55,212-2 XLR-11

D₂R agonists

Apomorphine
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).

GABA_AR agonists

Inhalants
Mixed MOA

κOR agonists

MAO inhibitors

σR agonists

Others

Psychoanaleptics: Antidementia agents (N06D)

Anticholinesterases

Others

: PSO/PSI

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Antiaddictives (N07B)

Nicotine dependence

Alcohol dependence

Opioid dependence

Benzodiazepine dependence

Amphetamine dependence

Cocaine dependence

: CNS

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Analgesics (N02A, N02B)

Opioids

Opiates/opium	Codeine^# Morphine^# Opium Laudanum Paregoric

Semisynthetic	Acetyldihydrocodeine Benzylmorphine Buprenorphine Desomorphine Diacetylmorphine (heroin) Dihydrocodeine Dihydromorphine Ethylmorphine Hydrocodone Hydromorphinol Hydromorphone Nicocodeine Nicodicodeine Nicomorphine Oxycodone Oxymorphone

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

Pyrazolones

Anilides

NSAIDs

Propionic acids	Fenoprofen Flurbiprofen Ibuprofen^# Ketoprofen Naproxen Oxaprozin

Oxicams	Meloxicam Piroxicam

Acetic acids	Diclofenac Indometacin Ketorolac Nabumetone Sulindac Tolmetin

COX-2 inhibitors	Celecoxib Lumiracoxib Parecoxib Rofecoxib Valdecoxib

Fenamates	Meclofenamic acid Mefenamic acid

Salicylates	Aspirin (acetylsalicylic acid)^# (+paracetamol/caffeine) Benorylate Diflunisal Ethenzamide Magnesium salicylate Salicin Salicylamide Salsalate Wintergreen (methyl salicylate)

Others	Glafenine

Cannabinoids

Channel modulators

Calcium blockers	Gabapentin Gabapentin enacarbil Pregabalin Ziconotide

Sodium blockers	Carbamazepine Lacosamide Local anesthetics (e.g., lidocaine) Mexiletine Nefopam Orphenadrine Tricyclic antidepressants (e.g., amitriptyline^#)

Potassium openers	Flupirtine

Monoaminergics

Muscle relaxants

Others

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

: CNS

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Anesthetic: General anesthetics (N01A)

Inhalational

Injection

Barbiturates	Hexobarbital Methohexital Narcobarbital Thiopental^# Thiotetrabarbital

Opioids	Alfentanil Anileridine^‡ Fentanyl Phenoperidine Remifentanil Sufentanil

Arylcyclohexylamines	Esketamine Ketamine^# Phencyclidine^‡ Tiletamine

Others	Alfadolone Alfaxalone Etomidate Fospropofol Hydroxydione GHB Metomidate Midazolam Propanidid^‡ Propofol

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

: CNS

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Nootropics

Ampakines	CX-516 CX-546 CX-614 Farampator (CX-691) CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org 26576 PEPA S-18986 Sunifiram Unifiram

Cholinergics	mAChR agonists: 77-LH-28-1 ADX-47273 Alvameline Arecoline Cevimeline CI-1017 Milameline Sabcomeline Talsaclidine Tazomeline Xanomeline nAChR agonists: AR-R17779 Bradanicline Cotinine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-282,987 Pozanicline Rivanicline SIB-1553A SSR-180,711 TC-1827 WAY-317,538 AChE inhibitors: Celastrus paniculatus Cymserine Donepezil Galantamine Huperzine A (Huperzia Serrata) Ladostigil Metrifonate Physostigmine Rivastigmine Tacrine Others: Alpha-GPC Choline Citicoline

Racetams	Aniracetam Brivaracetam Coluracetam Etiracetam Fasoracetam Levetiracetam Nebracetam Nefiracetam Oxiracetam Phenylpiracetam Piracetam Pramiracetam Rolziracetam Seletracetam

Nutrients	Acetylcarnitine Choline Omega-3 fatty acids Phosphatidylserine Pyritinol Sulbutiamine Thiamine

Others	Adafenoxate BAY 73-6691 Bifemelane Bilobalide (Ginkgo biloba) C16 Carbenoxolone Centella asiatica Cinnarizine Clitoria ternatea Cyprodenate Dimethylethanolamine Eleutherococcus senticosus Ergoloid Ensaculin Emoxypine Fipexide Guarana Idebenone Indeloxazine ISRIB Leteprinim Linopirdine Meclofenoxate (centrophenoxine) Methylene Blue Nizofenone Noopept NSI-189 P7C3 Pirisudanol PRL-8-53 Razobazam Rubidium S-17092 Semax Shilajit Taltirelin Teniloxazine Tianeptine Tricyanoaminopropene Uncaria tomentosa Vincamine Vinpocetine

Antidepressants (N06A)

Specific reuptake inhibitors and/or receptor modulators

SSRIs	Citalopram Escitalopram Fluoxetine^# Fluvoxamine Indalpine^‡ Paroxetine Sertraline Zimelidine^‡

SNRIs	Desvenlafaxine Duloxetine Levomilnacipran Milnacipran Tofenacin Venlafaxine

NRIs	Reboxetine Viloxazine

NDRIs	Amineptine^‡ Nomifensine^‡

SARIs	Etoperidone Nefazodone^‡ Trazodone

SMSs	Vilazodone Vortioxetine

Others	Agomelatine Amisulpride Buprenorphine Bupropion Etryptamine^‡ Ketamine Lurasidone Medifoxamine^‡ Metryptamine^‡ Oxaflozane^‡ Tandospirone Teniloxazine Tianeptine

Tricyclic antidepressants

TCAs	Amineptine^‡ Amitriptyline^# Amitriptylinoxide Butriptyline^‡ Clomipramine^# Demexiptiline^‡ Desipramine Dibenzepin Dimetacrine^‡ Dosulepin Doxepin Imipramine Imipraminoxide^‡ Iprindole^‡ Lofepramine Melitracen Metapramine^‡ Nitroxazepine Nortriptyline Noxiptiline Opipramol Pipofezine Propizepine^‡ Protriptyline Quinupramine^‡ Tianeptine Trimipramine

TeCAs	Amoxapine Maprotiline Mianserin Mirtazapine Setiptiline

Others	Tiazesim

Monoamine oxidase inhibitors

Non-selective	Irreversible: Benmoxin^‡ Iproclozide^‡ Iproniazid^‡ Isocarboxazid Mebanazine^‡ Nialamide^‡ Octamoxin^‡ Phenelzine Pheniprazine^‡ Phenoxypropazine^‡ Pivhydrazine^‡ Safrazine^‡ Tranylcypromine Reversible: Caroxazone^‡

MAO_A-selective	Reversible: Eprobemide Metralindole Minaprine^‡ Moclobemide Pirlindole Toloxatone

MAO_B-Selective	Irreversible: Selegiline

Adjunctive therapies

Atypical antipsychotics Buspirone Lithium (lithium carbonate, lithium citrate) Thyroid hormones (triiodothyronine (T₃), thyroxine (T₄))

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

: PSO/PSI

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proc (/), drug (/////)

Cholinergics

Receptor ligands

mACh	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 Choline cis-Dioxolane Ethoxysebacylcholine Itameline 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 Suberyldicholine 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 (ethybenztropine) 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 (e.g., brompheniramine chlorphenamine cyproheptadine dimenhydrinate diphenhydramine doxylamine mepyramine (pyrilamine) phenindamine pheniramine tripelennamine triprolidine) Tricyclic antidepressants (e.g., imipramine, amitriptyline) Tetracyclic antidepressants (e.g., amoxapine, maprotiline) Typical antipsychotics (e.g., chlorpromazine, thioridazine) Atypical antipsychotics (e.g., clozapine, olanzapine)

nACh	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 Butinoline Butyrylcholine Carbachol Choline Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium Epibatidine Epiboxidine Ethanol Ethoxysebacylcholine EVP-4473 EVP-6124 Galantamine GTS-21 Ispronicline Levamisole Lobeline MEM-63,908 (RG-3487) Morantel Nicotine (tobacco) NS-1738 PHA-543,613 PHA-709,829 PNU-120,596 PNU-282,987 Pozanicline Rivanicline RJR-2429 Sazetidine A Sebacylcholine SIB-1508Y SIB-1553A SSR-180,711 Suberyldicholine Suxamethonium (succinylcholine) 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-MAC 18-MC α-Bungarotoxin α-Conotoxin Alcuronium Allopregnanolone Amantadine Anatruxonium Atracurium Bupropion Chandonium Chlorisondamine Cisatracurium Coclaurine Coronaridine Cyclopropane Dacuronium Decamethonium Desflurane Dextromethorphan Dextropropoxyphene Dextrorphan Diadonium DHβE Dihydrochandonium Dimethyltubocurarine (metocurine) Dipyrandium Dizocilpine (MK-801) Doxacurium Enflurane Esketamine Fazadinium Gallamine Halothane Hexafluronium Hexamethonium (benzohexonium) Hydroxybupropion Ibogaine Isoflurane Ketamine Kynurenic acid Laudexium (laudolissin) Levacetylmethadol Levomethadone Malouetine ME-18-MC Mecamylamine Memantine Methadone Methorphan (racemethorphan) Methyllycaconitine Metocurine Mivacurium Morphanol (racemorphan) Neramexane Nitrous oxide Pancuronium bromide Pempidine Pentamine Pentolinium Phencyclidine Pipecuronium Progesterone Promegestone Radafaxine Rapacuronium Rocuronium Sevoflurane Surugatoxin Thiocolchicoside Toxiferine Tramadol Trimetaphan camsilate (trimethaphan camsylate) Tropeinium Tubocurarine Vanoxerine Vecuronium Xenon

Reuptake inhibitors

CHT	Hemicholinium-3 (hemicholine) Triethylcholine

VAChT	Vesamicol

Enzyme inhibitors

ChAT	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	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: Distigmine bromide Eptastigmine Ganstigmine Neostigmine Phenserine Physostigmine Pyridostigmine bromide Quilostigmine Rivastigmine Terestigmine; Others: Acotiamide Ambenonium Donepezil Caffeine Edrophonium Galantamine Huperzine A Ipidacrine Minaprine Tacrine Zanapezil Irreversible: Organophosphates: Acephate Azinphos-methyl Bensulide Cadusafos Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Cyclosarin Demeton Demeton-S-methyl Diazinon Dichlorvos Dicrotophos Diisopropyl fluorophosphate 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 Phoxim Pirimiphos-methyl Sarin Soman Tabun Tebupirimfos Temefos Terbufos Tetrachlorvinphos Tribufos Trichlorfon VE VG VM VR VX; Others: Demecarium Onchidal (Onchidella binneyi)

BChE	Cymserine Note: Many of the AChE inhibitors listed above also act as BChE inhibitors.

Others

Precursors	Choline (lecithin) Citicoline Cyprodenate Dimethylethanolamine Glycerophosphocholine Meclofenoxate (centrophenoxine) Phosphatidylcholine Phosphatidylethanolamine Phosphorylcholine Pirisudanol

Cofactors	Acetic acid Acetylcarnitine Acetyl-coA Vitamin B₅

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

Glutamatergics

Receptor
(ligands)

AMPA	Agonists: 5-Fluorowillardiine AMPA Domoic acid Quisqualic acid; Positive allosteric modulators: Aniracetam Cyclothiazide CX-516 CX-546 CX-614 Farampator (CX-691, Org 24448) CX-717 Diazoxide Hydrochlorothiazide (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 BGG492 Caroverine CNQX DNQX GYKI-52466 NBQX Perampanel Talampanel Tezampanel Topiramate; Negative allosteric modulators: Cyclopropane Ethanol GYKI-53,655 Pregnenolone sulfate

NMDA	Agonists: Glutamate/active 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 GLYX-13 HA-966 L-687,414 Milacemide NRX-1074 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 Lanicemine Loperamide Memantine Methadone (Levomethadone) Methorphan (Dextromethorphan Levomethorphan) Methoxetamine Milnacipran Morphanol (Dextrorphan Levorphanol) NEFA Neramexane Nitromemantine Nitrous oxide Noribogaine Orphenadrine PCPr Pethidine (meperidine) Phencyclamine Phencyclidine Propoxyphene Remacemide Rhynchophylline Rimantadine Rolicyclidine Sabeluzole Tenocyclidine Tiletamine Tramadol Xenon; Glycine site antagonists: ACEA-1021 ACEA-1328 ACC Carisoprodol CGP-39653 CKA DCKA Felbamate Gavestinel GV-196,771 Kynurenic acid L-689,560 L-701,324 Licostinel LU-73,068 MDL-105,519 Meprobamate MRZ 2/576 PNQX ZD-9379; NR2B subunit antagonists: Besonprodil CERC-301 (MK-0657) CO-101,244 (PD-174,494) 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 Cyclopropane Diethyl ether Diphenidine Enflurane Ethanol Halothane Isoflurane Methoxyflurane Toluene Trichloroethane Trichloroethanol Trichloroethylene Xylene

Kainate	Agonists: 5-Iodowillardiine ATPA Domoic acid Kainic acid LY-339,434 SYM-2081; Positive allosteric modulators: Cyclothiazide Diazoxide Antagonists: BGG492 CNQX DNQX LY-382,884 NBQX NS102 Tezampanel Topiramate UBP-302; Negative allosteric modulators: Ethanol NS-3763 Pregnenolone sulfate

Group I	Agonists: Non-selective: ACPD DHPG Quisqualic acid; mGlu1-selective: Ro01-6128 Ro67-4853 Ro67-7476 VU-71; mGlu5-selective: ADX-47273 CDPPB CHPG DFB VU-1545 Antagonists: Non-selective: MCPG NPS-2390; mGlu1-selective: BAY 36-7620 CPCCOEt LY-367,385 LY-456,236; mGlu5-selective: CTEP DMeOB LY-344,545 Mavoglurant SIB-1757 SIB-1893; Negative allosteric modulators: Basimglurant Dipraglurant Fenobam GRN-529 MPEP MTEP Raseglurant

Group II	Agonists: Non-selective: CBiPES DCG-IV Eglumegad LY-379,268 LY-404,039 LY-487,379 MGS-0028; mGlu2-selective: BINA LY-566,332 Antagonists: Non-selective: APICA EGLU HYDIA LY-307,452 LY-341,495 MCPG MGS-0039; mGlu2-selective: PCCG-4 mGlu3-selective: CECXG; Negative allosteric modulators: Decoglurant RO4491533

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

Transporter
(blockers)

EAATs	DHKA PDC WAY-213,613

vGluTs	7-CKA Evans blue

Others

Precursors: L-Glutamine

Neramexane

Neramexane

See also

References

Categories

Xenon

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Psychology

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Ethanol

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Psychiatry

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Morphine

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Nitromemantine

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