Butane

Butane
Names
	Preferred IUPAC name Butane
	Systematic IUPAC name Tetracarbane (never recommended)
	Other names Butyl hydride; Quartane; Refrigerant 3-11-0
Identifiers
CAS Number	106-97-8 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	969129
ChEBI	CHEBI:37808 ;
ChEMBL	ChEMBL134702 ;
ChemSpider	7555 ;
ECHA InfoCard	100.003.136
EC Number	203-448-7;
E number	E943a (glazing agents, ...)
Gmelin Reference	1148
KEGG	D03186 ;
MeSH	butane
PubChem CID	7843;
RTECS number	EJ4200000;
UNII	6LV4FOR43R ;
UN number	1011
CompTox Dashboard (EPA)	DTXSID7024665 ;
	show InChI
	show SMILES
Properties
Chemical formula	C4H10
Molar mass	58.124 g·mol−1
Appearance	Colorless gas
Odor	Gasoline-like or natural gas-like
Density	2.48 kg/m3 (at 15 °C (59 °F))
Melting point	−140 to −134 °C; −220 to −209 °F; 133 to 139 K
Boiling point	−1 to 1 °C; 30 to 34 °F; 272 to 274 K
Solubility in water	61 mg/L (at 20 °C (68 °F))
log P	2.745
Vapor pressure	~170 kPa at 283 K
Henry's law; constant (kH)	11 nmol Pa−1 kg−1
Conjugate acid	Butanium
Magnetic susceptibility (χ)	−57.4·10−6 cm3/mol
Thermochemistry
Heat capacity (C)	98.49 J/(K·mol)
Std enthalpy of; formation (ΔfH⦵298)	−126.3–−124.9 kJ/mol
Std enthalpy of; combustion (ΔcH⦵298)	−2.8781–−2.8769 MJ/mol
Hazards
Safety data sheet	See: data page
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H220
GHS precautionary statements	P210
NFPA 704 (fire diamond)	1 4 0 SA
Flash point	−60 °C (−76 °F; 213 K)
Autoignition; temperature	405 °C (761 °F; 678 K)
Explosive limits	1.8–8.4%
	NIOSH (US health exposure limits):
PEL (Permissible)	none
REL (Recommended)	TWA 800 ppm (1900 mg/m3)
IDLH (Immediate danger)	1600 ppm
Related compounds
Related alkanes	Propane; Isobutane; Pentane;
Related compounds	Perfluorobutane
Supplementary data page
Structure and; properties	Refractive index (n),; Dielectric constant (εr), etc.
Thermodynamic; data	Phase behaviour; solid–liquid–gas
Spectral data	UV, IR, NMR, MS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	(what is ?)
	Infobox references

Butane (/ˈbjuːteɪn/) or n-butane is an alkane with the formula C₄H₁₀. Butane is a gas at room temperature and atmospheric pressure. Butane is a highly flammable, colorless, easily liquefied gas that quickly vaporizes at room temperature. The name butane comes from the roots but- (from butyric acid, named after the Greek word for butter) and -ane. It was discovered by the chemist Edward Frankland in 1849.^[6] It was found dissolved in crude petroleum in 1864 by Edmund Ronalds, who was the first to describe its properties.^[7]^[8]

History[]

Butane was discovered by the chemist Edward Frankland in 1849. It was found dissolved in crude petroleum in 1864 by Edmund Ronalds, who was the first to describe its properties.

Isomers[]

Common name	normal butane unbranched butane n-butane	isobutane i-butane
IUPAC name	butane	methylpropane
Molecular diagram
Skeletal diagram

Rotation about the central C−C bond produces two different conformations (trans and gauche) for n-butane.^[9]

Reactions[]

Spectrum of the blue flame from a butane torch showing CH molecular radical band emission and C₂ Swan bands

When oxygen is plentiful, butane burns to form carbon dioxide and water vapor; when oxygen is limited, carbon (soot) or carbon monoxide may also be formed. Butane is denser than air.

When there is sufficient oxygen:

2 C₄H₁₀ + 13 O₂ → 8 CO₂ + 10 H₂O

When oxygen is limited:

2 C₄H₁₀ + 9 O₂ → 8 CO + 10 H₂O

By weight, butane contains about 49.5 MJ/kg (13.8 kWh/kg; 22.5 MJ/lb; 21,300 Btu/lb) or by liquid volume 29.7 megajoules per liter (8.3 kWh/l; 112 MJ/U.S. gal; 107,000 Btu/U.S. gal).

The maximum adiabatic flame temperature of butane with air is 2,243 K (1,970 °C; 3,578 °F).

n-Butane is the feedstock for DuPont's catalytic process for the preparation of maleic anhydride:

2 CH₃CH₂CH₂CH₃ + 7 O₂ → 2 C₂H₂(CO)₂O + 8 H₂O

n-Butane, like all hydrocarbons, undergoes free radical chlorination providing both 1-chloro- and 2-chlorobutanes, as well as more highly chlorinated derivatives. The relative rates of the chlorination is partially explained by the differing bond dissociation energies, 425 and 411 kJ/mol for the two types of C-H bonds.

Uses[]

Normal butane can be used for gasoline blending, as a fuel gas, fragrance extraction solvent, either alone or in a mixture with propane, and as a feedstock for the manufacture of ethylene and butadiene, a key ingredient of synthetic rubber. Isobutane is primarily used by refineries to enhance (increase) the octane number of motor gasoline.^[10]^[11]^[12]^[13]

When blended with propane and other hydrocarbons, it may be referred to commercially as LPG, for liquefied petroleum gas. It is used as a petrol component, as a feedstock for the production of base petrochemicals in steam cracking, as fuel for cigarette lighters and as a propellant in aerosol sprays such as deodorants.^[14]

Very pure forms of butane, especially isobutane, can be used as refrigerants and have largely replaced the ozone-layer-depleting halomethanes, for instance in household refrigerators and freezers. The system operating pressure for butane is lower than for the halomethanes, such as R-12, so R-12 systems such as in automotive air conditioning systems, when converted to pure butane will not function optimally and therefore a mix of isobutane and propane is used to give cooling system performance comparable to R-12.

Butane is also used as lighter fuel for a common lighter or butane torch and is sold bottled as a fuel for cooking, barbecues and camping stoves. Butane canisters global market is dominated by South Korean manufacturers.^[15]

As fuel, it is often mixed with small amounts of hydrogen sulfide and mercaptans which will give the unburned gas an offensive smell easily detected by the human nose. In this way, butane leaks can easily be identified. While hydrogen sulfide and mercaptans are toxic, they are present in levels so low that suffocation and fire hazard by the butane becomes a concern far before toxicity.^[16]^[17] Most commercially available butane also contains a certain amount of contaminant oil which can be removed through filtration but which will otherwise leave a deposit at the point of ignition and may eventually block the uniform flow of gas.^[18] The butane used in fragrance extraction does not contain these contaminants^[19] and butane gases can cause gas explosions in poorly ventilated areas if leaks go unnoticed and are ignited by spark or flame.^[5]Butane in its purest form is also used as a solvent in the industrial extraction of cannabis oils.

Butane fuel canisters for use in camping stoves
Butane lighter, showing liquid butane reservoir
An aerosol spray can, which may be using butane as a propellant
Butane gas cylinder used for cooking

Effects and health issues[]

Inhalation of butane can cause euphoria, drowsiness, unconsciousness, asphyxia, cardiac arrhythmia, fluctuations in blood pressure and temporary memory loss, when abused directly from a highly pressurized container, and can result in death from asphyxiation and ventricular fibrillation. It enters the blood supply and within seconds produces intoxication.^[20] Butane is the most commonly abused volatile substance in the UK, and was the cause of 52% of solvent related deaths in 2000.^[21] By spraying butane directly into the throat, the jet of fluid can cool rapidly to −20 °C (−4 °F) by expansion, causing prolonged laryngospasm.^[22] "Sudden sniffer's death" syndrome, first described by Bass in 1970,^[23] is the most common single cause of solvent related death, resulting in 55% of known fatal cases.^[22]

References[]

^ Jump up to: ^a ^b ^c ^d ^e NIOSH Pocket Guide to Chemical Hazards. "#0068". National Institute for Occupational Safety and Health (NIOSH).
^ Hofmann, August Wilhelm Von (1 January 1867). "I. On the action of trichloride of phosphorus on the salts of the aromatic monamines". Proceedings of the Royal Society of London. 15: 54–62. doi:10.1098/rspl.1866.0018. S2CID 98496840.
^ Jump up to: ^a ^b "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 4. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. Similarly, the retained names ‘ethane’, ‘propane’, and ‘butane’ were never replaced by systematic names ‘dicarbane’, ‘tricarbane’, and ‘tetracarbane’ as recommended for analogues of silane, ‘disilane’; phosphane, ‘triphosphane’; and sulfane, ‘tetrasulfane’.
^ W. B. Kay (1940). "Pressure-Volume-Temperature Relations for n-Butane". Industrial & Engineering Chemistry. 32 (3): 358–360. doi:10.1021/ie50363a016.
^ Jump up to: ^a ^b "Safety Data Sheet, Material Name: N-Butane" (PDF). USA: Matheson Tri-Gas Incorporated. 5 February 2011. Archived from the original (PDF) on 1 October 2011. Retrieved 11 December 2011.
^ Russel, Colin A. (20 March 2009). "Frankland – the First Organometallic Chemist" (PDF). The Sixth Wheeler Lecture. Royal Society of Chemistry. Archived from the original on 17 April 2017.CS1 maint: unfit URL (link)
^ Watts, H.; Muir, M. M. P.; Morley, H. F. (1894). Watts' Dictionary of Chemistry. Watts' Dictionary of Chemistry. Longmans, Green. p. 385.
^ Maybery, C. F. (1896). "On the Composition of the Ohio and Canadian Sulphur Petroleums". Proceedings of the American Academy of Arts and Sciences. 31: 1–66. doi:10.2307/20020618. JSTOR 20020618.
^ (2009). "Enthalpy Difference between Conformations of Normal Alkanes: Raman Spectroscopy Study of n-Pentane and n-Butane". J. Phys. Chem. A. 113 (6): 1012–9. doi:10.1021/jp809639s. PMID 19152252.
^ MarkWest Energy Partners, L.P. Form 10-K. Sec.gov.
^ Copano Energy, L.L.C. Form 10-K. Sec.gov. Retrieved on 2012-12-03.
^ Targa Resources Partners LP Form10-k. Sec.gov. Retrieved on 2012-12-03.
^ Crosstex Energy, L.P. FORM 10-K. Sec.gov.
^ A Primer on Gasoline Blending. An EPRINC Briefing Memorandum.
^ "Entrepreneur overcame hardships of Chinese prison". houstonchronicle.com. 21 June 2016. Retrieved 20 September 2018.
^ Gresham, Chip (16 November 2019). "Hydrogen Sulfide Toxicity: Practice Essentials, Pathophysiology, Etiology". Medscape Reference. Retrieved 22 March 2021.
^ Committee on Acute Exposure Guideline Levels; Committee on Toxicology; Board on Environmental Studies and Toxicology; Division on Earth and Life Studies; National Reserch Council (26 September 2013). 2. Methyl Mercaptan Acute Exposure Guideline Levels. NCBI Bookshelf.CS1 maint: multiple names: authors list (link)
^ "BHO Mystery Oil". Skunk Pharm Research. 26 August 2013. Retrieved 5 December 2019.
^ "Final Report of the Safety Assessment of Isobutane, Isopentane, n-Butane, and Propane". Journal of the American College of Toxicology. SAGE Publications. 1 (4): 127–142. 1982. doi:10.3109/10915818209021266. ISSN 0730-0913. S2CID 208503534.
^ "Neurotoxic Effects from Butane Gas". thcfarmer.com. 19 December 2009. Retrieved 3 October 2016.
^ Field-Smith M., Bland J. M., Taylor J. C. et al. "Trends in death Associated with Abuse of Volatile Substances 1971–2004" (PDF). Department of Public Health Sciences. London: St George’s Medical School. Archived from the original (PDF) on 27 March 2007.CS1 maint: uses authors parameter (link)
^ Jump up to: ^a ^b Ramsey J., Anderson H. R., Bloor K. et al. (1989). "An introduction to the practice, prevalence and chemical toxicology of volatile substance abuse". Hum Toxicol. 8 (4): 261–269. doi:10.1177/096032718900800403. PMID 2777265. S2CID 19617950.CS1 maint: uses authors parameter (link)
^ Bass M. (1970). "Sudden sniffing death". JAMA. 212 (12): 2075–2079. doi:10.1001/jama.1970.03170250031004. PMID 5467774.

External links[]

[PGCH-1] Jump up to: ^a ^b ^c ^d ^e NIOSH Pocket Guide to Chemical Hazards. "#0068". National Institute for Occupational Safety and Health (NIOSH).

[2] Hofmann, August Wilhelm Von (1 January 1867). "I. On the action of trichloride of phosphorus on the salts of the aromatic monamines". Proceedings of the Royal Society of London. 15: 54–62. doi:10.1098/rspl.1866.0018. S2CID 98496840.

[iupac2013-3] Jump up to: ^a ^b "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 4. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. Similarly, the retained names ‘ethane’, ‘propane’, and ‘butane’ were never replaced by systematic names ‘dicarbane’, ‘tricarbane’, and ‘tetracarbane’ as recommended for analogues of silane, ‘disilane’; phosphane, ‘triphosphane’; and sulfane, ‘tetrasulfane’.

[4] W. B. Kay (1940). "Pressure-Volume-Temperature Relations for n-Butane". Industrial & Engineering Chemistry. 32 (3): 358–360. doi:10.1021/ie50363a016.

[chemadvisor-5] Jump up to: ^a ^b "Safety Data Sheet, Material Name: N-Butane" (PDF). USA: Matheson Tri-Gas Incorporated. 5 February 2011. Archived from the original (PDF) on 1 October 2011. Retrieved 11 December 2011.

[6] Russel, Colin A. (20 March 2009). "Frankland – the First Organometallic Chemist" (PDF). The Sixth Wheeler Lecture. Royal Society of Chemistry. Archived from the original on 17 April 2017.CS1 maint: unfit URL (link)

[Watts-7] Watts, H.; Muir, M. M. P.; Morley, H. F. (1894). Watts' Dictionary of Chemistry. Watts' Dictionary of Chemistry. Longmans, Green. p. 385.

[8] Maybery, C. F. (1896). "On the Composition of the Ohio and Canadian Sulphur Petroleums". Proceedings of the American Academy of Arts and Sciences. 31: 1–66. doi:10.2307/20020618. JSTOR 20020618.

[Balabin_2009-9] (2009). "Enthalpy Difference between Conformations of Normal Alkanes: Raman Spectroscopy Study of n-Pentane and n-Butane". J. Phys. Chem. A. 113 (6): 1012–9. doi:10.1021/jp809639s. PMID 19152252.

[10] MarkWest Energy Partners, L.P. Form 10-K. Sec.gov.

[11] Copano Energy, L.L.C. Form 10-K. Sec.gov. Retrieved on 2012-12-03.

[12] Targa Resources Partners LP Form10-k. Sec.gov. Retrieved on 2012-12-03.

[13] Crosstex Energy, L.P. FORM 10-K. Sec.gov.

[14] A Primer on Gasoline Blending. An EPRINC Briefing Memorandum.

[15] "Entrepreneur overcame hardships of Chinese prison". houstonchronicle.com. 21 June 2016. Retrieved 20 September 2018.

[Gresham_2019-16] Gresham, Chip (16 November 2019). "Hydrogen Sulfide Toxicity: Practice Essentials, Pathophysiology, Etiology". Medscape Reference. Retrieved 22 March 2021.

[Toxicology2013-17] Committee on Acute Exposure Guideline Levels; Committee on Toxicology; Board on Environmental Studies and Toxicology; Division on Earth and Life Studies; National Reserch Council (26 September 2013). 2. Methyl Mercaptan Acute Exposure Guideline Levels. NCBI Bookshelf.CS1 maint: multiple names: authors list (link)

[18] "BHO Mystery Oil". Skunk Pharm Research. 26 August 2013. Retrieved 5 December 2019.

[SAGE-19] "Final Report of the Safety Assessment of Isobutane, Isopentane, n-Butane, and Propane". Journal of the American College of Toxicology. SAGE Publications. 1 (4): 127–142. 1982. doi:10.3109/10915818209021266. ISSN 0730-0913. S2CID 208503534.

[20] "Neurotoxic Effects from Butane Gas". thcfarmer.com. 19 December 2009. Retrieved 3 October 2016.

[21] Field-Smith M., Bland J. M., Taylor J. C. et al. "Trends in death Associated with Abuse of Volatile Substances 1971–2004" (PDF). Department of Public Health Sciences. London: St George’s Medical School. Archived from the original (PDF) on 27 March 2007.CS1 maint: uses authors parameter (link)

[multiple-22] Jump up to: ^a ^b Ramsey J., Anderson H. R., Bloor K. et al. (1989). "An introduction to the practice, prevalence and chemical toxicology of volatile substance abuse". Hum Toxicol. 8 (4): 261–269. doi:10.1177/096032718900800403. PMID 2777265. S2CID 19617950.CS1 maint: uses authors parameter (link)

[23] Bass M. (1970). "Sudden sniffing death". JAMA. 212 (12): 2075–2079. doi:10.1001/jama.1970.03170250031004. PMID 5467774.

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show v t GABA_A receptor positive modulators
Alcohols	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	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 Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Cloniprazepam Clorazepate Clotiazepam Cloxazolam CP-1414S Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam EVT-201 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	Ampelopsin (dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Luteolin Skullcap constituents (e.g., baicalin) Wogonin
Imidazoles	Etomidate Metomidate Propoxate
Kava constituents	Desmethoxyyangonin Kavain Methysticin Yangonin
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Carbromal
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 Pregnanolone (eltanolone) Progesterone Renanolone Testosterone THDOC Zuranolone
Nonbenzodiazepines	Cyclopyrrolones: Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone Imidazopyridines: Alpidem DS-1 Necopidem Saripidem Zolpidem Pyrazolopyrimidines: Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon Others: Adipiplon CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 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 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 Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole DEABL Dihydroergolines (e.g., dihydroergocryptine, , dihydroergotamine, ergoloid (dihydroergotoxine)) Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid 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 (e.g., sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, ) Unsorted benzodiazepine site positive modulators: α-Pinene
See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators

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