tert -Butyl alcohol Skeletal formula of tert -butyl alcohol Ball and stick model of tert -butyl alcohol
Names Preferred IUPAC name 2-Methylpropan-2-ol Other names t -Butyl alcoholtert -Butanolt -Butanolt -BuOHTrimethyl carbinol[ 1] Tertiary butanol 2-Methyl-2-propanol 2M2P Identifiers CAS Number 75-65-0 Y 3D model (JSmol) Beilstein Reference 906698 ChEBI CHEBI:45895 Y ChEMBL ChEMBL16502 Y ChemSpider 6146 Y DrugBank DB03900 Y ECHA InfoCard 100.000.809 EC Number Gmelin Reference 1833 MeSH tert-Butyl+Alcohol PubChem CID RTECS number UNII MD83SFE959 Y UN number 1120 CompTox Dashboard (EPA) DTXSID8020204 InChI InChI=1S/C4H10O/c1-4(2,3)5/h5H,1-3H3 Y Key: DKGAVHZHDRPRBM-UHFFFAOYSA-N Y SMILES Properties Chemical formula C 4H 10O Molar mass 74.123 g·mol−1 Appearance Colorless solid Odor Camphorous Density 0.775 g/mL Melting point 25 to 26 °C; 77 to 79 °F; 298 to 299 K Boiling point 82 to 83 °C; 179 to 181 °F; 355 to 356 K Solubility in water miscible[ 2] log P 0.584 Vapor pressure 4.1 kPa (at 20 °C) Acidity (pK a) 16.54 [ 3] Magnetic susceptibility (χ) 5.742× 10−5 cm3/mol Refractive index (n D) 1.387 Dipole moment 1.31 D Thermochemistry Heat capacity (C ) 215.37 J K−1 mol−1 Std molarentropy (S ⦵298) 189.5 J K−1 mol−1 Std enthalpy offormation (ΔfH ⦵298) −360.04 to −358.36 kJ mol−1 Std enthalpy ofcombustion (ΔcH ⦵298) −2.64479 to −2.64321 MJ mol−1 Hazards GHS labelling: Pictograms Signal word Danger Hazard statements H225, H319, H332, H335 Precautionary statements P210, P261, P305+P351+P338 NFPA 704 (fire diamond) 2 3 0 Flash point 11 °C (52 °F; 284 K) Autoignitiontemperature 480 °C (896 °F; 753 K) Explosive limits 2.4–8.0% Lethal dose or concentration (LD, LC): LD50 (median dose) 3559 mg/kg (rabbit, oral)3500 mg/kg (rat, oral)[ 4] NIOSH (US health exposure limits): PEL (Permissible) TWA 100 ppm (300 mg/m3)[ 1] REL (Recommended) TWA 100 ppm (300 mg/m3) ST 150 ppm (450 mg/m3)[ 1] IDLH (Immediate danger) 1600 ppm[ 1] Safety data sheet (SDS) inchem.org Related compounds Related butanols 2-Butanol n -Butanol Isobutanol
Related compounds 2-Methyl-2-butanol Trimethylsilanol Nonafluoro-tert-butyl alcohol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is Y N ?) Infobox references
Chemical compound
tert -Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t -BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert -Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.
Natural occurrence [ edit ] tert -Butyl alcohol has been identified in beer and chickpeas.[ 5] It is also found in cassava,[ 6] which is used as a fermentation ingredient in certain alcoholic beverages.
Preparation [ edit ] tert -Butyl alcohol is derived commercially from isobutane as a coproduct of propylene oxide production. It can also be produced by the catalytic hydration of isobutylene, or by a Grignard reaction between acetone and methylmagnesium chloride.
Purification cannot be performed by simple distillation due to formation of an azeotrope with water, although initial drying of the solvent containing large amounts of water is performed by adding benzene to form a tertiary azeotrope and distilling off the water. Smaller amounts of water are removed by drying with calcium oxide (CaO), potassium carbonate (K2CO3), calcium sulfate (CaSO4), or magnesium sulfate (MgSO4), followed by fractional distillation. Anhydrous tert -butyl alcohol is obtained by further refluxing and distilling from magnesium activated with iodine, or alkali metals such as sodium or potassium. Other methods include the use of 4 Å molecular sieves, aluminium tert -butylate, calcium hydride (CaH2), or fractional crystallization under inert atmosphere.[ 7]
Applications [ edit ] tert -Butyl alcohol is used as a solvent, ethanol denaturant, paint remover ingredient, and gasoline octane booster and oxygenate. It is a chemical intermediate used to produce methyl tert -butyl ether (MTBE) and ethyl tert -butyl ether (ETBE) by reaction with methanol and ethanol, respectively, and tert -butyl hydroperoxide (TBHP) by reaction with hydrogen peroxide.
Reactions [ edit ] Unlike other isomers of butanol, tert -butyl alcohol, as a tertiary alcohol, has no hydrogen atom next to hydroxy-group, which makes it resistant to oxidation to carbonyl compounds.
tert -Butyl alcohol is deprotonated with a strong base to give the alkoxide. Particularly common is potassium tert -butoxide, which is prepared by treating tert -butanol with potassium metal.[ 8]
K +
t -BuOH →
t -BuO−K+ +
1 / 2 H2
The tert -butoxide is a strong, non-nucleophilic base in organic chemistry. It readily abstracts acidic protons from substrates, but its steric bulk inhibits the group from participating in nucleophilic substitution, such as in a Williamson ether synthesis or an SN2 reaction.
tert -Butyl alcohol reacts with hydrogen chloride to form tert -butyl chloride.
O-Chlorination of tert-butyl alcohol with hypochlorous acid to give tert-butyl hypochlorite:[ 9]
(CH3)3COH + HOCl → (CH3)3COCl + H2O
Pharmacology and toxicology [ edit ] There is limited data on the pharmacology and toxicology of tert-butanol in humans and other animals.[ 10] Human exposure may occur due to fuel oxygenate metabolism. Tert-butanol is poorly absorbed through skin but rapidly absorbed if inhaled or ingested. Tert-butanol is irritating to skin or eyes. Toxicity of single doses is usually low but high doses can produce a sedative or anesthetic effect.
References [ edit ] ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0078". National Institute for Occupational Safety and Health (NIOSH). ^ "ICSC 0114 – tert -Butanol". Inchem.org . Retrieved 29 March 2018 . ^ Reeve, W.; Erikson, C. M.; Aluotto, P. F. (1979). "tert-Butyl alcohol". Can. J. Chem . 57: 2747. doi:10.1139/v79-444 . ^ "tert-Butyl alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH) . National Institute for Occupational Safety and Health (NIOSH). ^ "t -Butyl Alcohol". National Library of Medicine HSDB Database . National Institute for Health. Retrieved 29 March 2018 . ^ "Archived copy" (PDF) . Archived from the original (PDF) on 2016-03-04. Retrieved 2013-03-05 .{{cite web}}: CS1 maint: archived copy as title (link) ^ Perrin, D. D.; Armarego, W. L. F. (1988). Purification of Laboratory Chemicals ^ Johnson, W. S.; Schneider, W. P. (1950). "β-Carbethoxy-γ,γ-diphenylvinylacetic acid". Organic Syntheses . 30: 18. doi:10.15227/orgsyn.030.0018. ^ Mintz, H. M.; Walling, C. (1969). "t-Butyl Hypochlorite". Org. Synth . 49: 9. doi:10.15227/orgsyn.049.0009. ^ Douglas McGregor (2010). "Tertiary-Butanol: a toxicological review". Critical Reviews in Toxicology . 40 (8): 697–727. doi:10.3109/10408444.2010.494249. PMID 20722584. S2CID 26041562. External links [ edit ] International Chemical Safety Card 0114 NIOSH Pocket Guide to Chemical Hazards. "#0078". National Institute for Occupational Safety and Health (NIOSH). IPCS Environmental Health Criteria 65: Butanols: four isomers IPCS Health and Safety Guide 7: tert -Butanol Alcohols By consumption Alcohols found inalcoholic drinks 1-Propanol 2-Methyl-1-butanol Ethanol Isoamyl alcohol Isobutanol Phenethyl alcohol tert -Amyl alcoholtert -Butyl alcoholTryptophol Medical alcohol Ethchlorvynol Methylpentynol Methanol poisoning Toxic alcohols Isopropyl alcohol Methanol
Primaryalcohols (1°) Methanol 4-Methylcyclohexanemethanol Aminomethanol Cyclohexylmethanol Methoxymethanol Methylazoxymethanol Trifluoromethanol Ethanol 1-Aminoethanol 2,2,2-Trichloroethanol 2,2,2-Trifluoroethanol 2-(2-Ethoxyethoxy)ethanol 2-(2-Methoxyethoxy)ethanol 2-(2-Methoxyethoxy)ethanol 2-Butoxyethanol 2-Chloroethanol 2-Ethoxyethanol 2-Fluoroethanol 2-Mercaptoethanol 2-Methoxyethanol Aminoethylethanolamine Diethylethanolamine Dimethylethanolamine Ethanol Ethanolamine N ,N -DiisopropylaminoethanolN -MethylethanolaminePhenoxyethanol Tribromoethanol Butanol 2-Methyl-1-butanol Isobutanol n -Butanol Straight-chainsaturatedC1 — C9 Methanol Ethanol 1-Propanol 1-Butanol 1-Pentanol 1-Hexanol 1-Heptanol 1-Octanol (capryl) 1-Nonanol (pelargonic) Straight-chainsaturatedC10 — C19 1-Decanol (capric) 1-Undecanol (hendecyl) 1-Dodecanol (lauryl) 1-Tridecanol 1-Tetradecanol (myristyl) 1-Pentadecanol 1-Hexadecanol (cetyl / palmityl) 1-Heptadecanol 1-Octadecanol (stearyl) 1-Nonadecanol Straight-chainsaturatedC20 — C29 1-Icosanol (arachidyl) 1-Heneicosanol 1-Docosanol (behenyl) 1-Tricosanol 1-Tetracosanol (lignoceryl) 1-Pentacosanol 1-Hexacosanol (ceryl) 1-Heptacosanol 1-Octacosanol (cluytyl / montanyl) 1-Nonacosanol Straight-chainsaturatedC30 — C39 1-Triacontanol (melissyl / myricyl) 1-Hentriacontanol 1-Dotriacontanol (lacceryl) 1-Tritriacontanol 1-Tetratriacontanol (geddyl) 1-Pentatriacontanol 1-Hexatriacontanol 1-Heptatriacontanol 1-Octatriacontanol 1-Nonatriacontanol Straight-chainsaturatedC40 — C49 1-Tetracontanol 1-Hentetracontanol 1-Dotetracontanol 1-Tritetracontanol 1-Tetratetracontanol 1-Pentatetracontanol 1-Hexatetracontanol 1-Heptatetracontanol 1-Octatetracontanol 1-Nonatetracontanol
2-Ethylhexanol Allyl alcohol Anisyl alcohol Benzyl alcohol Cinnamyl alcohol Crotyl alcohol Furfuryl alcohol Isoamyl alcohol Neopentyl alcohol Nicotinyl alcohol Perillyl alcohol Phenethyl alcohol Prenol Propargyl alcohol Salicyl alcohol Tryptophol Vanillyl alcohol Veratrole alcohol Secondary alcohols (2°) 1-Phenylethanol 2-Butanol 2-Deoxyerythritol 2-Heptanol 3-Heptanol 2-Hexanol 3-Hexanol 3-Methyl-2-butanol 2-Nonanol 2-Octanol 2-Pentanol 3-Pentanol Cyclohexanol Cyclopentanol Cyclopropanol Diphenylmethanol Isopropanol Pinacolyl alcohol Pirkle's alcohol Propylene glycol methyl ether Tertiary alcohols (3°) 2-Methyl-2-pentanol 2-Methylheptan-2-ol 2-Methylhexan-2-ol 3-Methyl-3-pentanol 3-Methyloctan-3-ol Diacetone alcohol Ethchlorvynol Methylpentynol Nonafluoro-tert -butyl alcohol tert -Amyl alcoholtert -Butyl alcoholTriphenylethanol Triphenylmethanol Hydric alcohols Monohydric alcohols Methanol (C1) Ethanol (C2) Isopropanol (C3) 1-Butanol (C4) 1-Pentanol (C5) Cetyl alcohol (C16) Dihydric alcohols Ethylene glycol Propylene glycol Trihydric alcohols Polyhydric alcohols (sugar alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)
Amyl alcohols 2,2-Dimethylpropan-1-ol 2-Methylbutan-1-ol 2-Methylbutan-2-ol 3-Methylbutan-1-ol 3-Methylbutan-2-ol Pentan-1-ol Pentan-2-ol Pentan-3-ol Aromatic alcohols Benzyl alcohol 2,4-Dichlorobenzyl alcohol 3-Nitrobenzyl alcohol Saturatedfatty alcohols Cetostearyl alcohol Decanol Lauryl alcohol Myristyl alcohol Nonanol Octanol Tridecanol Undecanol Branched andunsaturatedfatty alcohols 3-Methyl-3-pentanol Erucyl alcohol Linolenyl alcohol Linoleyl alcohol Oleyl alcohol Palmitoleyl alcohol tert-Amyl alcohol tert-Butyl alcohol Sugar alcohols C1 — C7 Methylene glycol (C1) Ethylene glycol (C2) Glycerol (C3) Erythritol (C4) Threitol (C4) Arabitol (C5) Ribitol (C5) Xylitol (C5) Mannitol (C6) Sorbitol (C6) Galactitol (C6) Iditol (C6) Volemitol (C7) Deoxy sugar alcohols Cyclic sugar alcohols Glycylglycitols Maltitol Lactitol Isomalt Maltotriitol Maltotetraitol Polyglycitol
Terpene alcohols Monoterpene alcohols Borneol Citronellol Geraniol Linalool Menthol Nerol Rhodinol Terpineol Sesquiterpene alcohols Bisabolol Farnesol Nerolidol Patchoulol Diterpene alcohols
Dialcohols 1,4-Butanediol 1,5-Pentanediol 2-Methyl-2-propyl-1,3-propanediol Diethylpropanediol Ethylene glycol Trialcohols Sterols Cholesterol Ergosterol Lanosterol β-Sitosterol Stigmasterol Fluoroalcohols 1,3-Difluoro-2-propanol 2,2,2-Trifluoroethanol 2-Fluoroethanol Nonafluoro-tert -butyl alcohol Trifluoromethanol Preparations Substitution of haloalkane Carbonyl reduction Ether cleavage Hydrolysis of epoxide Hydration of alkene Ziegler process Reactions Deprotonation Protonation Alcohol oxidation Nucleophilic substitution Fischer–Speier esterification Williamson ether synthesis Elimination reaction Nucleophilic substitution of carbonyl group Friedel-Crafts alkylation Nucleophilic conjugate addition Transesterification
Hypnotics/sedatives (N05C) GABAA GABAB 1,4-Butanediol 4-Fluorophenibut Aceburic acid Baclofen GABOB GHB (sodium oxybate) GBL GVL Phenibut Tolibut H1 Antihistamines Captodiame Cyproheptadine Diphenhydramine Doxylamine Hydroxyzine Methapyrilene Perlapine Pheniramine Promethazine Propiomazine Antidepressants Serotonin antagonists and reuptake inhibitors Etoperidone Nefazodone Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc. Antipsychotics Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.
α2-Adrenergic Clonidine Detomidine Dexmedetomidine Lofexidine Medetomidine Romifidine Tizanidine Xylazine 5-HT2A Antidepressants 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
Melatonin Agomelatine Melatonin Ramelteon Tasimelteon Orexin Daridorexant Lemborexant Suvorexant α2δ VDCC Gabapentin Gabapentin enacarbil Mirogabalin Phenibut Pregabalin Others Cannabidiol Chlorophenylalkyldiols Fenpentadiol Metaglycodol Phenaglycodol Diethylpropanediol Evoxine Fenadiazole Guaifenesin-related muscle relaxants Chlorphenesin Mephenesin Mephenoxalone Metaxalone Methocarbamol Midaflur Opioids (e.g., morphine) Passion flower Scopolamine Trazodone UMB68 Valnoctamide
GABAA receptor positive modulators Alcohols Brometone Butanol Chloralodol Chlorobutanol (cloretone) Ethanol (alcohol) (alcoholic drink) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert -Butanol (2M2P)tert -Pentanol (2M2B)Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol Barbiturates (-)-DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital Benzodiazepines 2-Oxoquazepam 3-Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Bromazolam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Cloniprazepam Clorazepate Clotiazepam Cloxazolam CP-1414S Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Dimdazenil Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flunitrazolam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 Ro48-8684 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam (Ro5-2904) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam Carbamates Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Hydroxyphenamate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate Flavonoids 6-Methylapigenin Ampelopsin (dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc-OMe Skullcap constituents (e.g., baicalin) Wogonin Imidazoles Etomidate Metomidate Propoxate Kava constituents 10-Methoxyyangonin 11-Methoxyyangonin 11-Hydroxyyangonin Desmethoxyyangonin 11-Methoxy-12-hydroxydehydrokavain 7,8-Dihydroyangonin Kavain 5-Hydroxykavain 5,6-Dihydroyangonin 7,8-Dihydrokavain 5,6,7,8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride Ectylurea Neuroactive steroids Acebrochol Allopregnanolone (brexanolone) Alfadolone Alfaxalone 3α-Androstanediol Androstenol Androsterone Certain anabolic-androgenic steroids Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone ORG-20599 ORG-21465 P1-185 Posovolone Pregnanolone (eltanolone) Progesterone Renanolone SAGE-105 SAGE-324 SAGE-516 SAGE-689 SAGE-872 Testosterone THDOC Zuranolone Nonbenzodiazepines Cyclopyrrolones : EszopiclonePagoclone Pazinaclone Suproclone Suriclone Zopiclone Imidazopyridines : AlpidemDS-1 Necopidem Saripidem Zolpidem Pyrazolopyrimidines : DivaplonFasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon Others : AdipiplonCGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 CTP-354 ELB-139 GBLD-345 Imepitoin JM-1232 L-838,417 Lirequinil (Ro41-3696) NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TGSC01AA TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine Y-23684 Phenols Fospropofol Propofol Thymol Piperidinediones Glutethimide Methyprylon Piperidione Pyrithyldione Pyrazolopyridines Cartazolate Etazolate ICI-190,622 Tracazolate Quinazolinones Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164 Volatiles/gases Acetone Acetophenone Acetylglycinamide chloral hydrate Aliflurane Benzene Butane Butylene Centalun Chloral Chloral betaine Chloral hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane (methyl chloroform) Trichloroethylene Vinyl ether Others/unsorted 3-Hydroxybutanal α-EMTBL AA-29504 Alogabat Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole Darigabat DEABL Deuterated etifoxine Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine)) DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid KRM-II-81 Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol) Loreclezole Menthyl isovalerate (validolum) Monastrol Niacin Niacinamide Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol) Unsorted benzodiazepine site positive modulators: α-PineneMRK-409 (MK-0343) TCS-1105 TCS-1205 See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators
Glycine receptor modulators Receptor(ligands) GlyRTooltip Glycine receptor Agonists: β-Alanine β-ABA (BABA) β-AIBA Caesium D-Alanine D-Serine GABA Glycine Hypotaurine Ivermectin L-Alanine L-Proline L-Serine L-Threonine MDL-27531 Milacemide Picolinic acid Propofol Quisqualamine Sarcosine Taurine Positive modulators: Alcohols (e.g., brometone, chlorobutanol (chloretone), ethanol (alcohol), tert -butanol (2M2P), tribromoethanol, trichloroethanol, trifluoroethanol) Alkylbenzene sulfonate Anandamide Barbiturates (e.g., pentobarbital, sodium thiopental) Chlormethiazole D12-116 Dihydropyridines (e.g., nicardipine) Etomidate Ginseng constituents (e.g., ginsenosides (e.g., ginsenoside-Rf)) Glutamic acid (glutamate) Ivermectin Ketamine Neuroactive steroids (e.g., alfaxolone, pregnenolone (eltanolone), pregnenolone acetate, minaxolone, ORG-20599) Nitrous oxide Penicillin G Propofol Tamoxifen Tetrahydrocannabinol Triclofos Tropeines (e.g., atropine, bemesetron, cocaine, LY-278584, tropisetron, zatosetron) Volatiles/gases (e.g., chloral hydrate, chloroform, desflurane, diethyl ether (ether), enflurane, halothane, isoflurane, methoxyflurane, sevoflurane, toluene, trichloroethane (methyl chloroform), trichloroethylene) Xenon Zinc Antagonists: 2-Aminostrychnine 2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline N-Methylstrychnine N,N-Dimethylmuscimol Nipecotic acid Pitrazepin Pseudostrychnine Quinolines (e.g., 4-hydroxyquinoline, 4-hydroxyquinoline-3-carboxylic acid, 5,7-CIQA, 7-CIQ, 7-TFQ, 7-TFQA) RU-5135 Sinomenine Strychnine Thiocolchicoside Tutin Negative modulators: Amiloride Benzodiazepines (e.g., bromazepam, clonazepam, diazepam, flunitrazepam, flurazepam) Corymine Cyanotriphenylborate Daidzein Dihydropyridines (e.g., nicardipine, nifedipine, nitrendipine) Furosemide Genistein Ginkgo constituents (e.g., bilobalide, ginkgolides (e.g., ginkgolide A, ginkgolide B, ginkgolide C, ginkgolide J, ginkgolide M)) Imipramine NBQX Neuroactive steroids (e.g., 3α-androsterone sulfate, 3β-androsterone sulfate, deoxycorticosterone, DHEA sulfate, pregnenolone sulfate, progesterone) Opioids (e.g., codeine, dextromethorphan, dextrorphan, levomethadone, levorphanol, morphine, oripavine, pethidine, thebaine) Picrotoxin (i.e., picrotin and picrotoxinin) PMBA Riluzole Tropeines (e.g., bemesetron, LY-278584, tropisetron, zatosetron) Verapamil Zinc NMDARTooltip N-Methyl-D-aspartate receptor
Transporter(blockers) GlyT1Tooltip Glycine transporter 1 ACPPB ALX-5407 (NFPS) ASP2535 Bitopertin (RG1678/RO4917838) CP-802079 Ethanol (alcohol) Glycyldodecylamide GSK1018921 Iclepertin LY-2365109 Mardepodect ORG-24598 ORG-25935 (SCH-900435) Pesampator (BIIB-104, PF-04958242) PF-03463275 Sarcosine SNG-12 (Synapsinae) SSR-103,800 SSR-504,734 Tilapertin GlyT2Tooltip Glycine transporter 2 ALX-1393 Amoxapine Ethanol (alcohol) NAGly Opiranserin (VVZ-149) ORG-25543 VVZ-368
See also Receptor/signaling modulators GABA receptor modulators GABAA receptor positive modulators Ionotropic glutamate receptor modulators
Authority control databases: National
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