Acetone - Wikipedia

Organic compound ((CH3)2CO); simplest ketone Not to be confused with Acetoin. For the musical instrument company, see Ace Tone. For other uses, see Acetone (disambiguation). Acetone[1]

Names
IUPAC name Acetone[7]
Preferred IUPAC name Propan-2-one[8]
Systematic IUPAC name 2-Propanone
Other names Acetonum (Latin pronunciation: [aˈkeːtonum]) Dimethyl ketone[2] Dimethyl carbonyl Ketone propane[3] β-Ketopropane[2] Propanone[4] 2-Propanone[2] Pyroacetic spirit (archaic)[5] Spirit of Saturn (archaic)[6]
Identifiers
CAS Number	67-64-1 Y
3D model (JSmol)	Interactive image
3DMet	B00058
Beilstein Reference	635680
ChEBI	CHEBI:15347 Y
ChEMBL	ChEMBL14253 Y
ChemSpider	175 Y
ECHA InfoCard	100.000.602
EC Number	200-662-2
Gmelin Reference	1466
KEGG	D02311 Y
MeSH	Acetone
PubChem CID	180
RTECS number	AL3150000
UNII	1364PS73AF Y
UN number	1090
CompTox Dashboard (EPA)	DTXSID8021482
InChI InChI=1S/C3H6O/c1-3(2)4/h1-2H3 YKey: CSCPPACGZOOCGX-UHFFFAOYSA-N Y InChI=1/C3H6O/c1-3(2)4/h1-2H3Key: CSCPPACGZOOCGX-UHFFFAOYAF
SMILES CC(=O)C
Properties
Chemical formula	C3H6O
Molar mass	58.080 g·mol−1
Appearance	Colourless liquid
Odor	Pungent, fruity[9]
Density	0.7845 g/cm3 (25 °C)[10]
Melting point	−94.9 °C (−138.8 °F; 178.2 K)[10]
Boiling point	56.08 °C (132.94 °F; 329.23 K)[10]
Solubility in water	Miscible[10]
Solubility	Miscible in benzene, diethyl ether, methanol, chloroform, ethanol[10]
log P	−0.24[11]
Vapor pressure	9.39 kPa (0 °C) 30.6 kPa (25 °C) 374 kPa (100 °C) 2.8 MPa (200 °C)[2]
Acidity (pKa)	19.16 (H2O)[12] 26.5 (DMSO)[13]
Magnetic susceptibility (χ)	−33.8·10−6 cm3/mol[14]
Thermal conductivity	0.161 W/(m·K) (25 °C)[15]
Refractive index (nD)	1.3588 (20 °C)[10]
Viscosity	0.306 mPa·s (25 °C)[16]
Structure
Coordination geometry	Trigonal planar at C2
Molecular shape	Dihedral at C2
Dipole moment	2.88 D[17]
Thermochemistry[18]
Heat capacity (C)	126.3 J/(mol·K)
Std molarentropy (S⦵298)	199.8 J/(mol·K)
Std enthalpy offormation (ΔfH⦵298)	−248.4 kJ/mol
Std enthalpy ofcombustion (ΔcH⦵298)	−1.79 MJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Highly flammable
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H319, H336, H373
Precautionary statements	P210, P235, P260, P305+P351+P338
NFPA 704 (fire diamond)	1 3 0
Flash point	−20 °C (−4 °F; 253 K)[19]
Autoignitiontemperature	465[19] °C (869 °F; 738 K)
Explosive limits	2.5–12.8%[19]
Threshold limit value (TLV)	250 ppm[20] (STEL), 500 ppm[20] (C)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	5800 mg/kg (rat, oral) 3000 mg/kg (mouse, oral) 5340 mg/kg (rabbit, oral)[21]
LC50 (median concentration)	20,702 ppm (rat, 8 h)[21]
LCLo (lowest published)	45,455 ppm (mouse, 1 h)[21]
NIOSH (US health exposure limits):
PEL (Permissible)	1000 ppm (2400 mg/m3)[3]
REL (Recommended)	TWA 250 ppm (590 mg/m3)[3]
IDLH (Immediate danger)	2500 ppm[3]
Related compounds
Related compounds	Butanone Isopropyl alcohol Formaldehyde Urea Carbonic acid
Supplementary data page
Acetone (data page)
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

Chemical compound

Acetone (2-propanone or dimethyl ketone) is an organic compound with the formula (CH3)2CO.[22] It is the simplest and smallest ketone (>C=O). It is a colorless, highly volatile, and flammable liquid with a characteristic pungent odour, very reminiscent of the smell of pear drops.

Acetone is miscible with water and serves as an important organic solvent in industry, home, and laboratory. About 6.7 million tonnes were produced worldwide in 2010, mainly for use as a solvent and for production of methyl methacrylate and bisphenol A, which are precursors to widely used plastics.[23][24] It is a common building block in organic chemistry. It serves as a solvent in household products such as nail polish remover and paint thinner. It has volatile organic compound (VOC)-exempt status in the United States.[25]

Acetone is produced and disposed of in the human body through normal metabolic processes. It is normally present in blood and urine. People with diabetic ketoacidosis produce it in larger amounts. Ketogenic diets that increase ketone bodies (acetone, β-hydroxybutyric acid and acetoacetic acid) in the blood are used to counter epileptic attacks in children who suffer from refractory epilepsy.[26]

Name

[edit]

From the 17th century, and before modern developments in organic chemistry nomenclature, acetone was given many different names. They included "spirit of Saturn", which was given when it was thought to be a compound of lead and, later, "pyro-acetic spirit" and "pyro-acetic ester".[6]

Prior to the name "acetone" being coined by French chemists (see below), it was named "mesit" (from the Greek μεσίτης, meaning mediator) by Carl Reichenbach, who also claimed that methyl alcohol consisted of mesit and ethyl alcohol.[27][6] Names derived from mesit include mesitylene and mesityl oxide which were first synthesised from acetone.

Unlike many compounds with the acet- prefix which have a 2-carbon chain, acetone has a 3-carbon chain. That has caused confusion because there cannot be a ketone with 2 carbons. The prefix refers to acetone's relation to vinegar (acetum in Latin, also the source of the words "acid" and "acetic"), rather than its chemical structure.[28]

History

[edit]

Acetone was first produced by Andreas Libavius in 1606 by distillation of lead(II) acetate.[29][30]

In 1832, French chemist Jean-Baptiste Dumas and German chemist Justus von Liebig determined the empirical formula for acetone.[31][32] In 1833, French chemists Antoine Bussy and Michel Chevreul decided to name acetone by adding the suffix -one to the stem of the corresponding acid (viz, acetic acid) just as a similarly prepared product of what was then confused with margaric acid was named margarone.[33][28] By 1852, English chemist Alexander William Williamson realized that acetone was methyl acetyl;[34] the following year, the French chemist Charles Frédéric Gerhardt concurred.[35] In 1865, the German chemist August Kekulé published the modern structural formula for acetone.[36][37] Johann Josef Loschmidt had presented the structure of acetone in 1861,[38] but his privately published booklet received little attention. During World War I, Chaim Weizmann developed the process for industrial production of acetone (Weizmann Process).[39]

Production

[edit]

In 2010, the worldwide production capacity for acetone was estimated at 6.7 million tonnes per year.[40] With 1.56 million tonnes per year, the United States had the highest production capacity,[41] followed by Taiwan and China. The largest producer of acetone is INEOS Phenol, owning 17% of the world's capacity, with also significant capacity (7–8%) by Mitsui, Sunoco and Shell in 2010.[40] INEOS Phenol also owns the world's largest production site (420,000 tonnes/annum) in Beveren (Belgium). Spot price of acetone in summer 2011 was 1100–1250 USD/tonne in the United States.[42]

Current method

[edit]

Acetone is produced directly or indirectly from propene. Approximately 83% of acetone is produced via the cumene process;[24] as a result, acetone production is tied to phenol production. In the cumene process, benzene is alkylated with propylene to produce cumene, which is oxidized by air to produce phenol and acetone:

Other processes involve the direct oxidation of propylene (Wacker-Hoechst process), or the hydration of propylene to give 2-propanol, which is oxidized (dehydrogenated) to acetone.[24]

Older methods

[edit]

Previously, acetone was produced by the dry distillation of acetates, for example calcium acetate in ketonic decarboxylation.

Ca ( CH 3 COO ) 2 ⟶ CaO ( s ) + CO 2 ( g ) + ( CH 3 ) 2 CO ↓ {\displaystyle {\ce {Ca(CH3COO)2 -> CaO_{(s)}{}+ CO2_{(g)}{}+ (CH3)2CO v}}}

After that time, during World War I, acetone was produced using acetone-butanol-ethanol fermentation with Clostridium acetobutylicum bacteria, which was developed by Chaim Weizmann (later the first president of Israel) in order to help the British war effort,[24][43] in the preparation of Cordite.[44] This acetone-butanol-ethanol fermentation was eventually abandoned when newer methods with better yields were found.[24]

Chemical properties

[edit]

Acetone is reluctant to form a hydrate:[45]

(CH3)2C=O + H2O ⇌ (CH3)2C(OH)2 K = 10−3 M−1

Like most ketones, acetone exhibits the keto–enol tautomerism in which the nominal keto structure (CH3)2C=O of acetone itself is in equilibrium with the enol isomer (CH3)C(OH)=(CH2) (prop-1-en-2-ol). In acetone vapor at ambient temperature, only 2.4×10−7% of the molecules are in the enol form.[46]

In the presence of suitable catalysts, two acetone molecules also combine to form the compound diacetone alcohol (CH3)C=O(CH2)C(OH)(CH3)2, which on dehydration gives mesityl oxide (CH3)C=O(CH)=C(CH3)2. This product can further combine with another acetone molecule, with loss of another molecule of water, yielding phorone and other compounds.[47]

Acetone is a weak Lewis base that forms adducts with soft acids like I2 and hard acids like phenol. Acetone also forms complexes with divalent metals.[48][49]

Under ultraviolet light, acetone fluoresces..[50]

The flame temperature of pure acetone is 1980 °C.[51]

Polymerisation

[edit]

At its melting point (−96 °C) is claimed to polymers to give a white elastic solid, soluble in acetone, stable for several hours at room temperature. To do so, a vapor of acetone is co-condensed with magnesium as a catalyst onto a very cold surface.[52][53][54]

Natural occurrence

[edit]

Humans exhale several milligrams of acetone per day. It arises from decarboxylation of acetoacetate.[55][56] Small amounts of acetone are produced in the body by the decarboxylation of ketone bodies. Certain dietary patterns, including prolonged fasting and high-fat low-carbohydrate dieting, can produce ketosis, in which acetone is formed in body tissue. Certain health conditions, such as alcoholism and diabetes, can produce ketoacidosis, uncontrollable ketosis that leads to a sharp, and potentially fatal, increase in the acidity of the blood. Since it is a byproduct of fermentation, acetone is a byproduct of the distillery industry.[55]

Metabolism

[edit]

Acetone can then be metabolized either by CYP2E1 via methylglyoxal to D-lactate and pyruvate, and ultimately glucose/energy, or by a different pathway via propylene glycol to pyruvate, lactate, acetate (usable for energy) and propionaldehyde.[57][58][59]

Uses

[edit]

About a third of the world's acetone is used as a solvent, and a quarter is consumed as acetone cyanohydrin, a precursor to methyl methacrylate.[23]

Chemical intermediate

[edit]

Acetone is used to synthesize methyl methacrylate. It begins with the initial conversion of acetone to acetone cyanohydrin via reaction with hydrogen cyanide (HCN):

( CH 3 ) 2 CO + HCN ⟶ ( CH 3 ) 2 C ( OH ) CN {\displaystyle {\ce {(CH3)2CO + HCN -> (CH3)2C(OH)CN}}}

In a subsequent step, the nitrile is hydrolyzed to the unsaturated amide, which is esterified:

( CH 3 ) 2 C ( OH ) CN + CH 3 OH ⟶ CH 2 = C ( CH 3 ) CO 2 CH 3 + NH 3 {\displaystyle {\ce {(CH3)2C(OH)CN + CH3OH -> CH2=C(CH3)CO2CH3 + NH3}}}

The third major use of acetone (about 20%)[23] is synthesizing bisphenol A. Bisphenol A is a component of many polymers such as polycarbonates, polyurethanes, and epoxy resins. The synthesis involves the condensation of acetone with phenol:

( CH 3 ) 2 CO + 2 C 6 H 5 OH ⟶ ( CH 3 ) 2 C ( C 6 H 4 OH ) 2 + H 2 O {\displaystyle {\ce {(CH3)2CO + 2 C6H5OH -> (CH3)2C(C6H4OH)2 + H2O}}}

Many millions of kilograms of acetone are consumed in the production of the solvents methyl isobutyl alcohol and methyl isobutyl ketone. These products arise via an initial aldol condensation to give diacetone alcohol.[24]

2 ( CH 3 ) 2 CO ⟶ ( CH 3 ) 2 C ( OH ) CH 2 C ( O ) CH 3 {\displaystyle {\ce {2 (CH3)2CO -> (CH3)2C(OH)CH2C(O)CH3}}}

Condensation with acetylene gives 2-methylbut-3-yn-2-ol, precursor to synthetic terpenes and terpenoids.[60]

Solvent

[edit]

Acetone is a good solvent for many plastics and some synthetic fibers. It is used for thinning polyester resin, cleaning tools used with it, and dissolving two-part epoxies and superglue before they harden. It is used as one of the volatile components of some paints and varnishes. As a heavy-duty degreaser, it is useful in the preparation of metal prior to painting or soldering, and to remove rosin flux after soldering (to prevent adhesion of dirt and electrical leakage and perhaps corrosion or for cosmetic reasons), although it may attack some electronic components, such as polystyrene capacitors.[61]

Although itself flammable, acetone is used extensively as a solvent for the safe transportation and storage of acetylene, which cannot be safely pressurized as a pure compound. Vessels containing a porous material are first filled with acetone followed by acetylene, which dissolves into the acetone. One litre of acetone can dissolve around 250 litres of acetylene at a pressure of 10 bars (1.0 MPa).[62][63]

Acetone is used as a solvent by the pharmaceutical industry and as a denaturant in denatured alcohol.[64] Acetone is also present as an excipient in some pharmaceutical drugs.[65][needs update]

Lab and domestic solvent

[edit]

A variety of organic reactions employ acetone as a polar, aprotic solvent, e.g. the Jones oxidation.

Because acetone is cheap, volatile, and dissolves or decomposes with most laboratory chemicals, an acetone rinse is the standard technique to remove solid residues from laboratory glassware before a final wash.[66] Despite common desiccatory use, acetone dries only via bulk displacement and dilution. It forms no azeotropes with water (see azeotrope tables).[67] Acetone also removes certain stains from microscope slides.[68]

Acetone freezes well below −78 °C. An acetone/dry ice mixture cools many low-temperature reactions.[69] Make-up artists use acetone to remove skin adhesive from the netting of wigs and mustaches by immersing the item in an acetone bath, then removing the softened glue residue with a stiff brush.[70] Acetone is a main ingredient in many nail polish removers because it breaks down nail polish.[71] It is used for all types of nail polish removal, like gel nail polish, dip powder and acrylic nails.[72]

Biology

[edit]

Proteins precipitate in acetone.[73] The chemical modifies peptides, both at α- or ε-amino groups, and in a poorly understood but rapid modification of certain glycine residues.[73]

In pathology, acetone helps find lymph nodes in fatty tissues (such as the mesentery) for tumor staging.[74] The liquid dissolves the fat and hardens the nodes, making them easier to find.[75]

Medical

[edit]

Dermatologists use acetone with alcohol for acne treatments to chemically peel dry skin. Common agents used today for chemical peeling are salicylic acid, glycolic acid, azelaic acid, 30% salicylic acid in ethanol, and trichloroacetic acid (TCA). Prior to chemexfoliation, the skin is cleaned and excess fat removed in a process called defatting. Acetone, hexachlorophene, or a combination of these agents was used in this process.[76]

Acetone has been shown to have anticonvulsant effects in animal models of epilepsy, in the absence of toxicity, when administered in millimolar concentrations.[77] It has been hypothesized that the high-fat low-carbohydrate ketogenic diet used clinically to control drug-resistant epilepsy in children works by elevating acetone in the brain.[77] Because of their higher energy requirements, children have higher acetone production than most adults – and the younger the child, the higher the expected production. This indicates that children are not uniquely susceptible to acetone exposure. External exposures are small compared to the exposures associated with the ketogenic diet.[78]

Safety

[edit]

Acetone's most hazardous property is its extreme flammability. In small amounts, acetone burns with a dull blue flame; in larger amounts, fuel evaporation causes incomplete combustion and a bright yellow flame. When hotter than acetone's flash point of −20 °C (−4 °F), air mixtures of 2.5‑12.8% acetone (by volume) may explode or cause a flash fire. Vapors can flow along surfaces to distant ignition sources and flash back.

Static discharge may also ignite acetone vapors, though acetone has a very high ignition initiation energy and accidental ignition is rare.[79] Acetone's auto-ignition temperature is the relatively high 465 °C (869 °F);[19] moreover, auto-ignition temperature depends upon experimental conditions, such as exposure time, and has been quoted as high as 535 °C.[80] Even pouring or spraying acetone over red-glowing coal will not ignite it, due to the high vapour concentration and the cooling effect of evaporation.[79]

Acetone should be stored away from strong oxidizers, such as concentrated nitric and sulfuric acid mixtures.[81] It may also explode when mixed with chloroform in the presence of a base.[82][clarification needed] When oxidized without combustion, for example with hydrogen peroxide, acetone may form acetone peroxide, a highly unstable primary explosive. Acetone peroxide may be formed accidentally, e.g. when waste peroxide is poured into waste solvents.[83]

Toxicity

[edit]

Acetone occurs naturally as part of certain metabolic processes in the human body, and has been studied extensively and is believed to exhibit only slight toxicity in normal use. There is no strong evidence of chronic health effects if basic precautions are followed.[84] It is generally recognized to have low acute and chronic toxicity if ingested and/or inhaled.[85] Acetone is not currently regarded as a carcinogen, a mutagen, or a concern for chronic neurotoxicity effects.[79]

Acetone can be found as an ingredient in a variety of consumer products ranging from cosmetics to processed and unprocessed foods. Acetone has been rated as a generally recognized as safe (GRAS) substance when present in drinks, baked foods, desserts, and preserves at concentrations ranging from 5 to 8 mg/L.[85]

Acetone is however an irritant, causing mild skin and moderate-to-severe eye irritation. At high vapor concentrations, it may depress the central nervous system like many other solvents.[86] Acute toxicity for mice by ingestion (LD50) is 3 g/kg, and by inhalation (LC50) is 44 g/m3 over 4 hours.[87]

Environmental effects

[edit]

Although acetone occurs naturally in the environment in plants, trees, volcanic gases, forest fires, and as a product of the breakdown of body fat,[88] the majority of the acetone released into the environment is of industrial origin.[clarification needed] Acetone evaporates rapidly, even from water and soil. Once in the atmosphere, it has a 22-day half-life and is degraded by UV light via photolysis (primarily into methane and ethane.[89]) Consumption by microorganisms contributes to the dissipation of acetone in soil, animals, or waterways.[88]

EPA classification

[edit]

In 1995, the United States Environmental Protection Agency (EPA) removed acetone from the list of volatile organic compounds. The companies requesting the removal argued that it would "contribute to the achievement of several important environmental goals and would support EPA's pollution prevention efforts", and that acetone could be used as a substitute for several compounds that are listed as hazardous air pollutants (HAP) under section 112 of the Clean Air Act.[90] In making its decision EPA conducted an extensive review of the available toxicity data on acetone, which was continued through the 2000s. It found that the evaluable "data are inadequate for an assessment of the human carcinogenic potential of acetone".[9]

Extraterrestrial occurrence

[edit]

On 30 July 2015, scientists reported that upon the first touchdown of the Philae lander on comet 67P's surface, measurements by the COSAC and Ptolemy instruments revealed sixteen organic compounds, four of which were seen for the first time on a comet, including acetamide, acetone, methyl isocyanate, and propionaldehyde.[91][92][93]

References

[edit]

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2. ^ a b c d Acetone in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD)
3. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0004". National Institute for Occupational Safety and Health (NIOSH).
4. ^ Klamt, Andreas (2005). COSMO-RS: From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design. Elsevier. pp. 92–94. ISBN 978-0-444-51994-8.
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7. ^ ChemSpider lists 'acetone' as a valid, expert-verified name for what would systematically be called 'propan-2-one'.
8. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 723. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
9. ^ a b Toxicological Profile for Acetone. U.S. Environmental Protection Agency June 2022 p. 7
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46. ^ Hine, Jack; Arata, Kazushi (1976). "Keto-Enol Tautomerism. II. The Calorimetrical Determination of the Equilibrium Constants for Keto-Enol Tautomerism for Cyclohexanone and Acetone". Bulletin of the Chemical Society of Japan. 49 (11): 3089–3092. doi:10.1246/bcsj.49.3089.
47. ^ Sowa, John R. (2005). Catalysis of organic reactions. Boca Raton: Taylor & Francis. p. 363. ISBN 978-0-8247-2729-1. OCLC 67767141.
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51. ^ Haynes, p. 15.49
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Common sources

[edit]

• Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 978-1-4987-5429-3.

Further reading

[edit] Wikimedia Commons has media related to Acetone.

• International Chemical Safety Card 0087
• NIOSH Pocket Guide to Chemical Hazards
• Acetone Safety Data Sheet (SDS)
• Hazardous substances databank entry at the national library of medicine Archived 2018-12-04 at the Wayback Machine
• SIDS Initial Assessment Report for Acetone from the Organisation for Economic Co-operation and Development (OECD)
• Calculation of vapor pressure, liquid density, dynamic liquid viscosity, surface tension of acetone

v t e Cholesterol and steroid metabolic intermediates
Mevalonate pathway	to HMG-CoA Acetyl-CoA Acetoacetyl-CoA HMB HMB-CoA HMG-CoA Ketone bodies Acetone Acetoacetic acid β-Hydroxybutyric acid to DMAPP Mevalonic acid Phosphomevalonic acid 5-Diphosphomevalonic acid Isopentenyl pyrophosphate Dimethylallyl pyrophosphate Geranyl- Geranyl pyrophosphate Geranylgeranyl pyrophosphate Carotenoid Prephytoene diphosphate Phytoene
Non-mevalonate pathway	DOXP MEP CDP-ME CDP-MEP MEcPP HMB-PP IPP DMAPP
To Cholesterol	Farnesyl pyrophosphate Squalene 2,3-Oxidosqualene Lanosterol Lanosterol 14-demethyllanosterol 4alpha-Methylzymosterol Zymosterone Zymosterol Zymosterol Zymostenol Lathosterol 7-Dehydrocholesterol Cholesterol Zymosterol Cholesta-7,24-dien-3-ol 7-Dehydrodesmosterol Desmosterol Cholesterol
From Cholesterol to Steroid hormones	22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol See here instead.
Nonhuman	To Sitosterol Cycloartenol Cycloeucalenol Obtusifoliol 4α-methylfecosterol Isofucosterol 24-Methylenelophenol Sitosterol More Phytosterols see here instead. To Ergocalciferol Fecosterol Episterol Ergostatrienol Ergostatetraenol Ergosterol Ergocalciferol

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 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: 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 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-Pinene MRK-409 (MK-0343) TCS-1105 TCS-1205
See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators

v t e Molecules detected in outer space
Molecules	Diatomic Aluminium monochloride Aluminium monofluoride Aluminium(II) oxide Argonium Carbon cation Carbon monophosphide Carbon monosulfide Carbon monoxide Cyano radical Diatomic carbon Fluoromethylidynium Helium hydride ion Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Imidogen Sulfur mononitride Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfanyl Sulfur monoxide Titanium(II) oxide Triatomic Aluminium(I) hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen cyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene N2H+ Nitrous oxide Nitroxyl Ozone Methylidynephosphane Potassium cyanide Trihydrogen cation Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water Fouratoms Acetylene Ammonia Isocyanic acid Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methylene amidogen Methyl cation Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon monoxide Tricarbon monosulfide Thiocyanic acid Fiveatoms Ammonium ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster Sixatoms Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene Sevenatoms Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Propyne Methylamine Methyl isocyanate Vinyl alcohol Eightatoms Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methylcyanoacetylene Methyl formate Acrolein Nineatoms Acetamide Cyanohexatriyne Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Ethanethiol Propionitrile N-Methylformamide Tenatomsor more Acetone Benzene Benzonitrile Buckminsterfullerene (C60, C60+, fullerene, buckyball) C70 fullerene Cyanodecapentayne Ethylene glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propionaldehyde Butyronitrile Pyrimidine Heptatrienyl radical
Deuteratedmolecules	Ammonia Ammonium ion Formaldehyde Formyl radical Heavy water Hydrogen cyanide Hydrogen deuteride Hydrogen isocyanide Propyne N2D+ Trihydrogen cation
Unconfirmed	Anthracene Dihydroxyacetone Methoxyethane Glycine Graphene Hemolithin H2NCO+ Linear C5 Naphthalene cation Phosphine Pyrene Silylidyne
Related	Abiogenesis Astrobiology Astrochemistry Atomic and molecular astrophysics Chemical formula Circumstellar dust Circumstellar envelope Cosmic dust Cosmic ray Cosmochemistry Diffuse interstellar band Earliest known life forms Extraterrestrial life Extraterrestrial liquid water Forbidden mechanism Homochirality Intergalactic dust Interplanetary medium Interstellar medium Photodissociation region Iron–sulfur world theory Kerogen Molecules in stars Nexus for Exoplanet System Science Organic compound Outer space PAH world hypothesis Pseudo-panspermia Polycyclic aromatic hydrocarbon (PAH) RNA world hypothesis Spectroscopy Tholin
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