Butane

Not to be confused with butene, butyne, or Bhutan.

organic compound

Butane

Names
Preferred IUPAC name Butane[3]
Systematic IUPAC name Tetracarbane (never recommended[3])
Other names Butyl hydride[1] Quartane[2]
Identifiers
CAS Number	106-97-8 Y
3D model (JSmol)	Interactive image
Beilstein Reference	969129
ChEBI	CHEBI:37808 Y
ChEMBL	ChEMBL134702 Y
ChemSpider	7555 Y
ECHA InfoCard	100.003.136
EC Number	203-448-7
E number	E943a (glazing agents, ...)
Gmelin Reference	1148
KEGG	D03186 Y
MeSH	butane
PubChem CID	7843
RTECS number	EJ4200000
UNII	6LV4FOR43R Y
UN number	1011
CompTox Dashboard (EPA)	DTXSID7024665
InChI InChI=1S/C4H10/c1-3-4-2/h3-4H2,1-2H3 Y Key: IJDNQMDRQITEOD-UHFFFAOYSA-N Y
SMILES CCCC
Properties
Chemical formula	C4H10
Molar mass	7001581240000000000♠58.124 g·mol−1
Appearance	Colorless gas
Odor	Gasoline-like or natural gas-like[1]
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−1 (at 20 °C (68 °F))
log P	2.745
Vapor pressure	~170 kPa at 283 K [4]
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−1 mol−1
Std enthalpy of formation (ΔfHo298)	−126.3–−124.9 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	−2.8781–−2.8769 MJ mol−1
Hazards[5]
Safety data sheet	See: data page
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H220
GHS precautionary statements	P210
NFPA 704	4 1 0 SA
Flash point	−60 °C (−76 °F; 213 K)
Autoignition temperature	405 °C (761 °F; 678 K)
Explosive limits	1.8–8.4%
US health exposure limits (NIOSH):
PEL (Permissible)	none[1]
REL (Recommended)	TWA 800 ppm (1900 mg/m3)[1]
IDLH (Immediate danger)	N.D.[1]
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).
Y verify (what is YN ?)
Infobox references

Butane (/ˈbjuːteɪn/) is an organic compound with the formula C₄H₁₀ that is an alkane with four carbon atoms. Butane is a gas at room temperature and atmospheric pressure. The term may refer to either of two structural isomers, n-butane or isobutane (also called "methylpropane"), or to a mixture of these isomers. In the IUPAC nomenclature, however, "butane" refers only to the n-butane isomer (which is the isomer with the unbranched structure). Butanes are highly flammable, colorless, easily liquefied gases that quickly vaporize 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]

Contents

• 
  1 Isomers
  


• 
  2 Reactions
  


• 
  3 Uses
  


• 
  4 Effects and health issues
  


• 
  5 See also
  


• 
  6 References
  


• 
  7 External links
  

Isomers

Common name	normal butane unbranched butane n-butane	isobutane i-butane
IUPAC name	butane	2-methylpropane
Molecular diagram
Skeletal diagram

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

Reactions

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Spectrum of the blue flame from a butane torch showing CH molecular radical band emission and C₂Swan 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.

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

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 are almost exclusively manufactured in South Korea with the only exception being one manufacturer in Houston, Texas.^[15] Butane canisters manufactured in South Korea contain butane from Saudi Arabia, while the American manufacturer fills canisters with domestic butane.^[16]

In this form 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. 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. Contaminants are not used in fragrance extraction and butane gasses can cause gas explosions in poorly ventilated areas if leaks go unnoticed and are ignited by spark or flame.

Butane fuel canisters for use in camping stoves.	Butane lighter, showing liquid butane reservoir	Butane being sprayed from an aerosol spray can	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.^[17] Butane is the most commonly misused volatile substance in the UK, and was the cause of 52% of solvent related deaths in 2000.^[18] By spraying butane directly into the throat, the jet of fluid can cool rapidly to −20 °C (−4 °F) by expansion, causing prolonged laryngospasm.^[19] "Sudden sniffer's death" syndrome, first described by Bass in 1970,^[20] is the most common single cause of solvent related death, resulting in 55% of known fatal cases.^[19]

A small amount of nitrogen dioxide, a toxic gas, results from burning butane gas, along with any combustion in the earth's atmosphere, and represents a human health hazard from home heaters and stoves.^[21]

See also

• Isobutane


• Cyclobutane


• Dimethyl ether


• Volatile substance abuse


• Butane (data page)


• Butanone


• 
  n-Butanol


• Liquefied petroleum gas


• Industrial gas


• Butane torch


• Gas explosions

References

1. 
   ^ ^abcde NIOSH Pocket Guide to Chemical Hazards. "#0068". National Institute for Occupational Safety and Health (NIOSH)..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output .citation q{quotes:"""""""'""'"}.mw-parser-output .citation .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-maint{display:none;color:#33aa33;margin-left:0.3em}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}
   


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. Retrieved 20 September 2018 – via rspl.royalsocietypublishing.org.
   


3. 
   ^ ^ab "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.
   


5. 
   ^ "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. 
   ^ "Occ paper" (PDF). www.chem.qmul.ac.uk.
   


7. 
   ^ Watts, H. (1868). Dictionary of Chemistry. 4. p. 385.
   


8. 
   ^ Maybery, C.F. (1896). "On the Composition of the Ohio and Canadian Sulphur Petroleums". Proc. American Academy Arts and Sciences. 31: 1–66.
   


9. 
   ^ Roman M. Balabin (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.
    


16. 
    ^ http://www.washingtontimes.com, The Washington Times. "Houston entrepreneur overcame hardships Chinese prison". washingtontimes.com. Retrieved 20 September 2018.
    


17. 
    ^ "Neurotoxic Effects from Butane Gas". thcfarmer.com. 19 Dec 2009. Retrieved 3 October 2016.
    


18. 
    ^ Field-Smith M, Bland JM, Taylor JC, 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 March 27, 2007.
    


19. 
    ^ ^ab Ramsey J, Anderson HR, 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.
    


20. 
    ^ Bass M. (1970). "Sudden sniffing death". JAMA. 212 (12): 2075–2079. doi:10.1001/jama.1970.03170250031004. PMID 5467774.
    


21. 
    ^ Ghosn, Marwan; Flouty, Roula; Saliba, Najat A. (2005). "Emission of Nitrogen Dioxide from Butane Gas Heaters and Stoves Indoors". American Journal of Applied Sciences. 2 (3): 707. doi:10.3844/ajassp.2005.707.710.
    

External links

Wikimedia Commons has media related to Butane.

• International Chemical Safety Card 0232


• NIOSH Pocket Guide to Chemical Hazards

v t e Alkanes
Methane (CH 4) Ethane (C 2H 6) Propane (C 3H 8) Butane (C 4H 10) Pentane (C 5H 12) Hexane (C 6H 14) Heptane (C 7H 16) Octane (C 8H 18) Nonane (C 9H 20) Decane (C 10H 22) Undecane (C 11H 24) Dodecane (C 12H 26) Tridecane (C 13H 28) Tetradecane (C 14H 30) Pentadecane (C 15H 32) Hexadecane / Cetane (C 16H 34) Heptadecane (C 17H 36) Octadecane (C 18H 38) Nonadecane (C 19H 40) Icosane (C 20H 42) Heneicosane (C 21H 44) Tetracosane (C 24H 50) Nonacosane (C 29H 60) Hentriacontane (C 31H 64)
Higher alkanes List of alkanes

v t e Binary compounds of hydrogen
Alkali metal hydrides	LiH NaH KH RbH CsH	Lithium hydride, LiH ionic metal hydride Beryllium hydride Left (gas phase): BeH2 covalent metal hydride Right: (BeH2)n (solid phase) polymeric metal hydride Borane and diborane Left: BH3 (special conditions), covalent metalloid hydride Right: B2H6 (standard conditions), dimeric metalloid hydride Methane, CH4 covalent nonmetal hydride Ammonia, NH3 covalent nonmetal hydride Water, H2O covalent nonmetal hydride Hydrogen fluoride, HF covalent nonmetal hydride
Alkaline earth hydrides	Monohydrides BeH MgH CaH SrH BaH Dihydrides BeH2 MgH2 CaH2 SrH2 BaH2
Group 13 hydrides	Boranes BH3 B2H6 B2H2 B2H4 B4H10 B5H9 B5H11 B6H10 B6H12 B10H14 B18H22 Alanes AlH3 Al2H6 Gallanes GaH3 Ga2H6 Indiganes InH3 In2H6 Thallanes TlH3 Tl2H6
Group 14 hydrides	Linear alkanes CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 more... Linear alkenes C2H4 C3H6 C4H8 C5H10 C6H12 C7H14 C8H16 C9H18 C10H20 more... Linear alkynes C2H2 C3H4 C4H6 C5H8 C6H10 C7H12 C8H14 C9H16 C10H18 more... Silanes SiH4 Si2H6 Si3H8 Si4H10 Si5H12 Si6H14 Si7H16 Si8H18 Si9H20 Si10H22 more... Silenes Si2H4 Silynes Si2H2 SiH Germanes GeH4 Ge2H6 Ge3H8 Ge4H10 Ge5H12 Stannanes SnH4 Sn2H6 Plumbanes PbH4 CH CH2 CH3 C2H Cycloalkanes Cycloalkenes Annulenes Many more
Pnictogen hydrides	Azanes NH3 N2H4 N3H5 N4H6 N5H7 N6H8 N7H9 N8H10 N9H11 N10H12 more... Azenes N2H2 N3H3 N4H4 Phosphanes PH3 P2H4 P3H5 P4H6 P5H7 P6H8 P7H9 P8H10 P9H11 P10H12 more... Phosphenes P2H2 P3H3 P4H4 Arsanes AsH3 As2H4 Stibanes SbH3 Bismuthanes BiH3 HN3 NH radical
Hydrogen chalcogenides	Polyoxidanes H2O H2O2 H2O3 H2O4 H2O5 H2O6 H2O7 H2O8 H2O9 H2O10 more... Polysulfanes H2S H2S2 H2S3 H2S4 H2S5 H2S6 H2S7 H2S8 H2S9 H2S10 more... Selanes H2Se H2Se2 Tellanes H2Te H2Te2 Polanes PoH2 HO HO2 HO3 H2O+–O– H2S=S (HS)2S+–S– HS HDO D2O T2O
Hydrogen halides	HF HCl HBr HI HAt
Transition metal hydrides	ScH2 YH2 YH3 TiH2 ZrH2 HfH2 VH VH2 NbH NbH2 TaH CrH CrH2 CrHx NiH PdHx (x < 1) FeH FeH2 FeH5 CuH ZnH2 CdH2 HgH2
Lanthanide hydrides	LaH2 LaH3 LaH10 CeH2 CeH3 PrH2 PrH3 NdH2 NdH3 SmH2 SmH3 EuH2 GdH2 GdH3 TbH2 TbH3 DyH2 DyH3 HoH2 HoH3 ErH2 ErH3 TmH2 TmH3 YbH2 YbH2.5 LuH2 LuH3
Actinide hydrides	AcH2 ThH2 Th4H15 PaH3 UH3 NpH2 NpH3 PuH2 PuH3 AmH2 AmH3 CmH2

v t e E numbers

Colors (E100–199) Preservatives (E200–299) Antioxidants & acidity regulators (E300–399) Thickeners, stabilisers & emulsifiers (E400–499) pH regulators & anticaking agents (E500–599) Flavour enhancers (E600–699) Miscellaneous (E900–999) Additional chemicals (E1100–1599) Waxes (E900–909) Synthetic glazes (E910–919) Improving agents (E920–929) Packaging gases (E930–949) Sweeteners (E950–969) Foaming agents (E990–999) Calcium peroxide (E930) Argon (E938) Helium (E939) Dichlorodifluoromethane (E940) Nitrogen (E941) Nitrous oxide (E942) Butane (E943a) Isobutane (E943b) Propane (E944) Oxygen (E948) Hydrogen (E949)

v t e 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 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 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 Pregnanolone (eltanolone) Progesterone Renanolone SAGE-105 SAGE-324 SAGE-516 SAGE-689 SAGE-872 Testosterone THDOC Zuranolone
Nonbenzodiazepines	β-Carbolines: Abecarnil Gedocarnil Harmane SL-651,498 ZK-93423 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 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 Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole DEABL 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 Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol) Loreclezole Menthyl isovalerate (validolum) Monastrol Niacin Nicotinamide (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-Pinene MRK-409 (MK-0343) TCS-1105 TCS-1205
See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators

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