Propene

Propene
Names
	Preferred IUPAC name Propene
Identifiers
CAS Number	115-07-1 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:16052 ;
ChEMBL	ChEMBL117213 ;
ChemSpider	7954 ;
ECHA InfoCard	100.003.693
KEGG	C11505 ;
PubChem CID	8252;
RTECS number	UC6740000;
UNII	AUG1H506LY ;
UN number	1077; In Liquefied petroleum gas: 1075
CompTox Dashboard (EPA)	DTXSID5021205 ;
	show InChI
	show SMILES
Properties
Chemical formula	C3H6
Molar mass	42.081 g·mol−1
Appearance	Colorless gas
Density	1.81 kg/m3, gas (1.013 bar, 15 °C); 1.745 kg/m3, gas (1.013 bar, 25 °C); 613.9 kg/m3, liquid
Melting point	−185.2 °C (−301.4 °F; 88.0 K)
Boiling point	−47.6 °C (−53.7 °F; 225.6 K)
Solubility in water	0.61 g/m3
Magnetic susceptibility (χ)	-31.5·10−6 cm3/mol
Viscosity	8.34 µPa·s at 16.7 °C
Structure
Dipole moment	0.366 D (gas)
Hazards
Safety data sheet	External MSDS
EU classification (DSD) (outdated)
R-phrases (outdated)	12
S-phrases (outdated)	9-16-33
NFPA 704 (fire diamond)	1 4 1
Flash point	−108 °C (−162 °F; 165 K)
Related compounds
Related alkenes;; related groups	Ethylene, Isomers of Butylene;; Allyl, Propenyl
Related compounds	Propane, Propyne; Propadiene, 1-Propanol; 2-Propanol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	(what is ?)
	Infobox references

Propene, also known as propylene, is an unsaturated organic compound with the chemical formula ${\ce {CH3CH=CH2}}$ . It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petroleum-like odor.^[2]

Production[]

Steam cracking[]

The dominant technology for producing propylene is steam cracking. The same technology is applied to ethane to ethylene. These two conversions are the #2 and #1 processes in the chemical industry, as judged by their scale.^[3] In this process, propane undergoes dehydrogenation. The by-product is hydrogen:

CH₃CH₂CH₃ → CH₃CH=CH₂ + H₂

The yield of propene is about 85 m%. By-products are usually used as fuel for the propane dehydrogenation reaction. Steam cracking is one of the most energy-intensive industrial processes.

The feedstock is naphtha or propane, especially in the Middle East, where there is an abundance of propane from oil/gas operations.^[4] Propene can be separated by fractional distillation from hydrocarbon mixtures obtained from cracking and other refining processes; refinery-grade propene is about 50 to 70%.^[5] In the United States, shale gas is a major source of propane.

Olefin conversion technology[]

In the Phillips Triolefin or Olefin conversion technology propylene is interconverted with ethylene and 2-butenes. Rhenium and molybdenum catalysts are used:^[6]

CH₂=CH₂ + CH₃CH=CHCH₃ → 2 CH₂=CHCH₃

The technology is founded on an olefin metathesis reaction discovered at Phillips Petroleum Company.^[7]^[8] Propene yields of about 90 wt% are achieved.

Related is the Methanol-to-Olefins/Methanol-to-Propene process. It converts synthesis gas (syngas) to methanol, and then converts the methanol to ethylene and/or propene. The process produces water as by-product. Synthesis gas is produced from |the reformation of natural gas or by the steam-induced reformation of petroleum products such as naphtha, or by gasification of coal.

Fluid catalytic cracking[]

High severity fluid catalytic cracking (FCC) uses traditional FCC technology under severe conditions (higher catalyst-to-oil ratios, higher steam injection rates, higher temperatures, etc.) in order to maximize the amount of propene and other light products. A high severity FCC unit is usually fed with gas oils (paraffins) and residues, and produces about 20–25 m% propene on feedstock together with greater volumes of motor gasoline and distillate byproducts. These high temperature processes are expensive and have a high carbon footprint. For these reasons, alternative routes to propylene continue to attract attention.^[9]

Market and research[]

Propene production has remained static at around 35 million tonnes (Europe and North America only) from 2000 to 2008, but it has been increasing in East Asia, most notably Singapore and China.^[10] Total world production of propene is currently about half that of ethylene.

The use of engineered enzymes has been explored but is of no commercial value.^[11]

Uses[]

Propene is the second most important starting product in the petrochemical industry after ethylene. It is the raw material for a wide variety of products. Polypropylene manufacturers consume nearly two thirds of global production.^[12] Polypropylene end uses include films, fibers, containers, packaging, and caps and closures. Propene is also used for the production of important chemicals such as propylene oxide, acrylonitrile, cumene, butyraldehyde, and acrylic acid. In the year 2013 about 85 million tonnes of propene were processed worldwide.^[12]

Propene and benzene are converted to acetone and phenol via the cumene process.

Propene is also used to produce isopropanol (propan-2-ol), acrylonitrile, propylene oxide, and epichlorohydrin.^[13] The industrial production of acrylic acid involves the catalytic partial oxidation of propene.^[14] Propene is also an intermediate in the one-step propane selective oxidation to acrylic acid.^[15]^[16]^[17]^[18] In industry and workshops, propene is used as an alternative fuel to acetylene in Oxy-fuel welding and cutting, brazing and heating of metal for the purpose of bending. It has become a standard in BernzOmatic products and others in MAPP substitutes,^[19] now that true MAPP gas is no longer available.

Reactions[]

Propene resembles other alkenes in that it undergoes addition reactions relatively easily at room temperature. The relative weakness of its double bond explains its tendency to react with substances that can achieve this transformation. Alkene reactions include: 1) polymerization, 2) oxidation, 3) halogenation and hydrohalogenation, 4) alkylation, 5) hydration, 6) oligomerization, and 7) hydroformylation.

Complexes of transition metals[]

Foundational to hydroformylation, alkene metathesis, and polymerization are metal-propylene complexes, which are intermediates in these processes. Propylene is prochiral, meaning that binding of a reagent (such as a metal electrophile) to the C=C group yields one of two enantiomers.

Polymerization[]

The majority of propene is used to form polypropylene, a very important commodity thermoplastic, through chain-growth polymerization.^[12] In the presence of a suitable catalyst (typically a Ziegler–Natta catalyst), propene will polymerize. There are multiple ways to achieve this, such as using high pressures to suspending the catalyst in a solution of liquid propene, or running gaseous propene through a fluidized bed reactor.^[20]

Combustion[]

Propene burns in a similar fashion to other alkenes. In the presence of sufficient or excess oxygen, propene burns to form water and carbon dioxide.

2 C₃H₆ + 9 O₂ → 6 CO₂ + 6 H₂O

Environmental safety[]

Propene is a product of combustion from forest fires, cigarette smoke, and motor vehicle and aircraft exhaust. It is an impurity in some heating gases. Observed concentrations have been in the range of 0.1-4.8 parts per billion (ppb) in rural air, 4-10.5 ppb in urban air, and 7-260 ppb in industrial air samples.^[5]

In the United States and some European countries a threshold limit value of 500 parts per million (ppm) was established for occupational (8-hour time-weighted average) exposure. It is considered a volatile organic compound (VOC) and emissions are regulated by many governments, but it is not listed by the U.S. Environmental Protection Agency (EPA) as a hazardous air pollutant under the Clean Air Act. With a relatively short half-life, it is not expected to bioaccumulate.^[5]

Propene has low acute toxicity from inhalation and is not considered to be carcinogenic. Chronic toxicity studies in mice did not yield significant evidence suggesting adverse effects. Humans briefly exposed to 4,000 ppm did not experience any noticeable effects.^[21] Propene is dangerous from its potential to displace oxygen as an asphyxiant gas, and from its high flammability/explosion risk.

Bio-propylene is the bio-based propylene.^[22]^[23] It has been examined, motivated by diverse interests such a carbon footprint. Production from glucose has been considered.^[24] More advance ways of addressing such issues focus on electrification alternatives to steam cracking.

Storage and handling[]

Propene is flammable. Propene is usually stored as liquid under pressure, although it is also possible to store it safely as gas at ambient temperature in approved containers.^[25]

Occurrence in nature[]

Propene is detected in the interstellar medium through microwave spectroscopy.^[26] On September 30, 2013, NASA also announced that the Cassini orbiter spacecraft, part of the Cassini-Huygens mission, had discovered small amounts of naturally occurring propene in the atmosphere of Titan using spectroscopy.^[27]^[28]

References[]

^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 31. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ "Propylene".
^ Giovanni Maggini (2013-04-17). "Technology Economics: Propylene via Propane Dehydrogenation, Part 3". Slideshare.net. Retrieved 2013-11-12.
^ Ashford’s Dictionary of Industrial Chemicals, Third edition, 2011, ISBN 978-0-9522674-3-0, pages 7766-9
^ Jump up to: ^a ^b ^c "Product Safety Assessment(PSA): Propylene". Dow Chemical Co. Archived from the original on 2013-06-22. Retrieved 2011-07-11.
^ Ghashghaee, Mohammad (2018). "Heterogeneous catalysts for gas-phase conversion of ethylene to higher olefins". Rev. Chem. Eng. 34 (5): 595–655. doi:10.1515/revce-2017-0003. S2CID 103664623.
^ Banks, R. L.; Bailey, G. C. (1964). "Olefin Disproportionation. A New Catalytic Process". Industrial & Engineering Chemistry Product Research and Development. 3 (3): 170–173. doi:10.1021/i360011a002.
^ Lionel Delaude, Alfred F. Noels (2005). "Metathesis". Kirk-Othmer Encyclopedia of Chemical Technology. Weinheim: Wiley-VCH. doi:10.1002/0471238961.metanoel.a01. ISBN 978-0471238966.CS1 maint: uses authors parameter (link)
^ Schiffer, Zachary J.; Manthiram, Karthish (2017). "Electrification and Decarbonization of the Chemical Industry". Joule. 1: 10–14. doi:10.1016/j.joule.2017.07.008. hdl:1721.1/124019.
^ Amghizar, Ismaël; Vandewalle, Laurien A.; Van Geem, Kevin M.; Marin, Guy B. (2017). "New Trends in Olefin Production". Engineering. 3 (2): 171–178. doi:10.1016/J.ENG.2017.02.006.
^ de Guzman, Doris (October 12, 2012). "Global Bioenergies in bio-propylene". Green Chemicals Blog.
^ Jump up to: ^a ^b ^c "Market Study: Propylene (2nd edition), Ceresana, December 2014". ceresana.com. Retrieved 2015-02-03.
^ Budavari, Susan, ed. (1996). "8034. Propylene". The Merck Index, Twelfth Edition. New Jersey: Merck & Co. pp. 1348–1349.
^ J.G.L., Fierro (Ed.) (2006). Metal Oxides, Chemistry and Applications. CRC Press. pp. 414–455.CS1 maint: extra text: authors list (link)
^ Naumann d'Alnoncourt, Raoul; Csepei, Lénárd-István; Hävecker, Michael; et al. (March 2014). "The reaction network in propane oxidation over phase-pure MoVTeNb M1 oxide catalysts". Journal of Catalysis. 311: 369–385. doi:10.1016/j.jcat.2013.12.008. hdl:11858/00-001M-0000-0014-F434-5.
^ Amakawa, Kazuhiko; Kolen'Ko, Yury V.; Villa, Alberto; et al. (7 June 2013). "Multifunctionality of Crystalline MoV(TeNb) M1 Oxide Catalysts in Selective Oxidation of Propane and Benzyl Alcohol". ACS Catalysis. 3 (6): 1103–1113. doi:10.1021/cs400010q. hdl:11858/00-001M-0000-000E-FA39-1.
^ Hävecker, Michael; Wrabetz, Sabine; Kröhnert, Jutta; et al. (January 2012). "Surface chemistry of phase-pure M1 MoVTeNb oxide during operation in selective oxidation of propane to acrylic acid". Journal of Catalysis. 285 (1): 48–60. doi:10.1016/j.jcat.2011.09.012. hdl:11858/00-001M-0000-0012-1BEB-F.
^ Csepei, Lénárd-István (2011). Kinetic studies of propane oxidation on Mo and V based mixed oxide catalysts. pp. 3–24, 93. doi:10.14279/depositonce-2972.
^ For example, "MAPP-Pro"
^ Heggs, T. Geoffrey (2011-10-15), Wiley-VCH Verlag GmbH & Co. KGaA (ed.), "Polypropylene", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, pp. o21_o04, doi:10.1002/14356007.o21_o04, ISBN 978-3-527-30673-2, retrieved 2021-07-09
^ PubChem. "Hazardous Substances Data Bank (HSDB) : 175". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-07-09.
^ Bio-based drop-in, smart drop-in and dedicated chemicals
^ Duurzame bioplastics op basis van hernieuwbare grondstoffen
^ Guzman, Doris de. "Global Bioenergies in bio-propylene". Green Chemicals Blog. Retrieved 2021-07-09.
^ Encyclopedia of Chemical Technology, Fourth edition, 1996, ISBN 0471-52689-4 (v.20), page 261
^ Marcelino, N.; Cernicharo, J.; Agúndez, M.; et al. (2007-08-10). "Discovery of Interstellar Propylene (CH2CHCH3): Missing Links in Interstellar Gas-Phase Chemistry". The Astrophysical Journal. IOP. 665 (2): L127–L130. doi:10.1086/521398. S2CID 15832967.
^ "Spacecraft finds propylene on Saturn moon, Titan". UPI.com. 2013-09-30. Retrieved 2013-11-12.
^ "Cassini finds ingredient of household plastic on Saturn moon". Spacedaily.com. Retrieved 2013-11-12.

[iupac2013-1] "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 31. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[2] "Propylene".

[3] Giovanni Maggini (2013-04-17). "Technology Economics: Propylene via Propane Dehydrogenation, Part 3". Slideshare.net. Retrieved 2013-11-12.

[4] Ashford’s Dictionary of Industrial Chemicals, Third edition, 2011, ISBN 978-0-9522674-3-0, pages 7766-9

[Dow-5] Jump up to: ^a ^b ^c "Product Safety Assessment(PSA): Propylene". Dow Chemical Co. Archived from the original on 2013-06-22. Retrieved 2011-07-11.

[MG-6] Ghashghaee, Mohammad (2018). "Heterogeneous catalysts for gas-phase conversion of ethylene to higher olefins". Rev. Chem. Eng. 34 (5): 595–655. doi:10.1515/revce-2017-0003. S2CID 103664623.

[7] Banks, R. L.; Bailey, G. C. (1964). "Olefin Disproportionation. A New Catalytic Process". Industrial & Engineering Chemistry Product Research and Development. 3 (3): 170–173. doi:10.1021/i360011a002.

[KO-8] Lionel Delaude, Alfred F. Noels (2005). "Metathesis". Kirk-Othmer Encyclopedia of Chemical Technology. Weinheim: Wiley-VCH. doi:10.1002/0471238961.metanoel.a01. ISBN 978-0471238966.CS1 maint: uses authors parameter (link)

[9] Schiffer, Zachary J.; Manthiram, Karthish (2017). "Electrification and Decarbonization of the Chemical Industry". Joule. 1: 10–14. doi:10.1016/j.joule.2017.07.008. hdl:1721.1/124019.

[realityck-10] Amghizar, Ismaël; Vandewalle, Laurien A.; Van Geem, Kevin M.; Marin, Guy B. (2017). "New Trends in Olefin Production". Engineering. 3 (2): 171–178. doi:10.1016/J.ENG.2017.02.006.

[11] Guzman, Doris (October 12, 2012). "Global Bioenergies in bio-propylene". Green Chemicals Blog.

[Ceresana-12] Jump up to: ^a ^b ^c "Market Study: Propylene (2nd edition), Ceresana, December 2014". ceresana.com. Retrieved 2015-02-03.

[13] Budavari, Susan, ed. (1996). "8034. Propylene". The Merck Index, Twelfth Edition. New Jersey: Merck & Co. pp. 1348–1349.

[14] J.G.L., Fierro (Ed.) (2006). Metal Oxides, Chemistry and Applications. CRC Press. pp. 414–455.CS1 maint: extra text: authors list (link)

[15] Naumann d'Alnoncourt, Raoul; Csepei, Lénárd-István; Hävecker, Michael; et al. (March 2014). "The reaction network in propane oxidation over phase-pure MoVTeNb M1 oxide catalysts". Journal of Catalysis. 311: 369–385. doi:10.1016/j.jcat.2013.12.008. hdl:11858/00-001M-0000-0014-F434-5.

[16] Amakawa, Kazuhiko; Kolen'Ko, Yury V.; Villa, Alberto; et al. (7 June 2013). "Multifunctionality of Crystalline MoV(TeNb) M1 Oxide Catalysts in Selective Oxidation of Propane and Benzyl Alcohol". ACS Catalysis. 3 (6): 1103–1113. doi:10.1021/cs400010q. hdl:11858/00-001M-0000-000E-FA39-1.

[17] Hävecker, Michael; Wrabetz, Sabine; Kröhnert, Jutta; et al. (January 2012). "Surface chemistry of phase-pure M1 MoVTeNb oxide during operation in selective oxidation of propane to acrylic acid". Journal of Catalysis. 285 (1): 48–60. doi:10.1016/j.jcat.2011.09.012. hdl:11858/00-001M-0000-0012-1BEB-F.

[18] Csepei, Lénárd-István (2011). Kinetic studies of propane oxidation on Mo and V based mixed oxide catalysts. pp. 3–24, 93. doi:10.14279/depositonce-2972.

[19] For example, "MAPP-Pro"

[:0-20] Heggs, T. Geoffrey (2011-10-15), Wiley-VCH Verlag GmbH & Co. KGaA (ed.), "Polypropylene", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, pp. o21_o04, doi:10.1002/14356007.o21_o04, ISBN 978-3-527-30673-2, retrieved 2021-07-09

[21] PubChem. "Hazardous Substances Data Bank (HSDB) : 175". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-07-09.

[22] Bio-based drop-in, smart drop-in and dedicated chemicals

[23] Duurzame bioplastics op basis van hernieuwbare grondstoffen

[24] Guzman, Doris de. "Global Bioenergies in bio-propylene". Green Chemicals Blog. Retrieved 2021-07-09.

[25] Encyclopedia of Chemical Technology, Fourth edition, 1996, ISBN 0471-52689-4 (v.20), page 261

[26] Marcelino, N.; Cernicharo, J.; Agúndez, M.; et al. (2007-08-10). "Discovery of Interstellar Propylene (CH2CHCH3): Missing Links in Interstellar Gas-Phase Chemistry". The Astrophysical Journal. IOP. 665 (2): L127–L130. doi:10.1086/521398. S2CID 15832967.

[27] "Spacecraft finds propylene on Saturn moon, Titan". UPI.com. 2013-09-30. Retrieved 2013-11-12.

[28] "Cassini finds ingredient of household plastic on Saturn moon". Spacedaily.com. Retrieved 2013-11-12.

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show v t Alkenes
Alkenes	Ethene ( C ₂H ₄ ) Propene ( C ₃H ₆ ) Butene ( C ₄H ₈ ) Pentene ( C ₅H ₁₀ ) Hexene ( C ₆H ₁₂ ) Heptene ( C ₇H ₁₄ ) Octene ( C ₈H ₁₆ ) Nonene ( C ₉H ₁₈ ) Decene ( C ₁₀H ₂₀ )
Preparations	Dehydrohalogenation from haloalkane Dehydration reaction from alcohol Semihydrogenation from alkyne Bamford–Stevens reaction Barton–Kellogg reaction Boord olefin synthesis Chugaev elimination Cope reaction Corey–Winter olefin synthesis Grieco elimination Hofmann elimination Horner–Wadsworth–Emmons reaction Hydrazone iodination Julia olefination Kauffmann olefination McMurry reaction Peterson olefination Ramberg–Bäcklund reaction Shapiro reaction Takai olefination Wittig reaction Olefin metathesis Ene reaction Cope rearrangement
Reactions	Hydrogenation Halogenation Hydration Electrophilic addition Oxymercuration reaction Hydroboration Cyclopropanation Epoxidation Dihydroxylation Ozonolysis Hydrohalogenation Polymerization Diels–Alder reaction Wacker process Dehydrogenation Ene reaction Friedel-Crafts Alkylation

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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