Methanol

CH3OH; simplest possible alcohol

Not to be confused with menthol, methanal, menthone, methadol, methabol, or ethanol.

Methanol  | Space filling model of methanol | Ball and stick model of methanol

|

A sample of methanol
Names
Preferred IUPAC name

Methanol[1]

Other names

Carbinol
Columbian spirits
Hydroxymethane
MeOH
Methyl alcohol
Methyl hydrate
Methyl hydroxide
Methylic alcohol
Methylol
Methylene hydrate, primary alcohol
Pyroligneous spirit
Wood alcohol
Wood naphtha
Wood spirit

Identifiers

CAS Number

* 67-56-1 Y

3D model (JSmol)

* Interactive image

Beilstein Reference

| 1098229
ChEBI |

* CHEBI:17790 Y

ChEMBL |

* ChEMBL14688 Y

ChemSpider |

* 864 Y

ECHA InfoCard | 100.000.599
EC Number |

* 200-659-6

Gmelin Reference

| 449
KEGG |

* D02309 Y

MeSH | Methanol

PubChem CID

* 887

RTECS number |

* PC1400000

UNII |

* Y4S76JWI15 Y

UN number | 1230

CompTox Dashboard (EPA)

* DTXSID2021731

InChI

* InChI=1S/CH4O/c1-2/h2H,1H3 Y

Key: OKKJLVBELUTLKV-UHFFFAOYSA-N Y

* InChI=1/CH4O/c1-2/h2H,1H3

Key: OKKJLVBELUTLKV-UHFFFAOYAX

SMILES

* CO

Properties

Chemical formula

| CH3OH
Molar mass | 32.042 g·mol−1
Appearance  | Colourless liquid
Odor | Faint and similar to ethanol
Density | 0.792 g/cm3[2]
Melting point | −97.6 °C (−143.7 °F; 175.6 K)
Boiling point | 64.7 °C (148.5 °F; 337.8 K)

Solubility in water

| miscible
log P | −0.69
Vapor pressure | 13.02 kPa (at 20 °C)
Acidity (pKa)  | 15.5[3]
Conjugate acid | Methyloxonium[4]
Conjugate base | Methanolate[5]

Magnetic susceptibility (χ)

| −21.40·10−6 cm3/mol

Refractive index (nD)

| 1.33141[6]
Viscosity | 0.545 mPa·s (at 25 °C)[7]

Dipole moment

| 1.69 D
Thermochemistry

Heat of combustion, higher value (HHV)

| 725.7 kJ/mol, 173.4 kcal/mol, 5.77 kcal/g
Hazards[12][13]
Occupational safety and health (OHS/OSH):

Main hazards

| Methanol and its vapours are flammable.

Moderately toxic for small animals – Highly toxic to large animals and humans (in high concentrations) – May be fatal/lethal or cause blindness and damage to the liver, kidneys, and heart if swallowed – Toxicity effects from repeated over exposure have an accumulative effect on the central nervous system, especially the optic nerve – Symptoms may be delayed, become severe after 12 to 18 hours, and linger for several days after exposure[9]

GHS labelling:

Pictograms

| [8]

Signal word

| Danger[8]

Hazard statements

| H225, H301, H302, H305, H311, H331, H370[8]

Precautionary statements

| P210, P233, P235, P240, P241, P242, P243, P260, P264, P270, P271, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P310, P311, P312, P337+P313, P361, P363, P370+P378, P403+P233, P405, P501[8]
NFPA 704 (fire diamond)  |

[12][14]

Flash point | 11 to 12 °C (52 to 54 °F; 284 to 285 K)

Autoignition
temperature

| 470 °C (878 °F; 743 K)[15]

385 °C (725 °F; 658 K)[16]

Explosive limits | 6–36%[10]
Lethal dose or concentration (LD, LC):

LD50 (median dose)

| 5628 mg/kg (rat, oral)
7300 mg/kg (mouse, oral)
12880 mg/kg (rat, oral)
14200 mg/kg (rabbit, oral)[11]

LC50 (median concentration)

| 64,000 ppm (rat, 4 h)[11]

LCLo (lowest published)

| 33,082 ppm (cat, 6 h)
37,594 ppm (mouse, 2 h)[11]
NIOSH (US health exposure limits):

PEL (Permissible)

| TWA 200 ppm (260 mg/m3)[10]

REL (Recommended)

| TWA 200 ppm (260 mg/m3) ST 250 ppm (325 mg/m3) [skin][10]

IDLH (Immediate danger)

| 6000 ppm[10]
Safety data sheet (SDS)  | [1]
Related compounds

Related compounds

| Methanethiol
Silanol
Ethanol
Supplementary data page
Methanol (data page)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)

Infobox references

Chemical compound

Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic alcohol, with the chemical formula CH3OH (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a light, volatile, colorless and flammable liquid with a distinctive alcoholic odor similar to that of ethanol (potable alcohol), but is more acutely toxic than the latter.[17] Methanol acquired the name wood alcohol because it was once produced through destructive distillation of wood. Today, methanol is mainly produced industrially by hydrogenation of carbon monoxide.[18]

Methanol consists of a methyl group linked to a polar hydroxyl group. With more than 20 million tons produced annually, it is used as a precursor to other commodity chemicals, including formaldehyde, acetic acid, methyl tert-butyl ether, methyl benzoate, anisole, peroxyacids, as well as a host of more specialized chemicals.[18]

## Occurrence

[edit]

Small amounts of methanol are present in normal, healthy human individuals. One study found a mean of 4.5 ppm in the exhaled breath of test subjects.[19] The mean endogenous methanol in humans of 0.45 g/d may be metabolized from pectin found in fruit; one kilogram of apple produces up to 1.4 g of pectin (0.6 g of methanol.)[20]

Methanol is produced by anaerobic bacteria and phytoplankton.[21][22]

### Interstellar medium

[edit]

Methanol is also found in abundant quantities in star-forming regions of space and is used in astronomy as a marker for such regions. It is detected through its spectral emission lines.[23]

In 2006, astronomers using the MERLIN array of radio telescopes at Jodrell Bank Observatory discovered a large cloud of methanol in space 0.463 terametres (288 million miles) across.[24][25] In 2016, astronomers detected methanol in a planet-forming disc around the young star TW Hydrae using the Atacama Large Millimeter Array radio telescope.[26]

## History

[edit]

In their embalming process, the ancient Egyptians used a mixture of substances, including methanol, which they obtained from the pyrolysis of wood. Pure methanol, however, was first isolated in 1661 by Robert Boyle, when he produced it via the distillation of buxus (boxwood).[27] It later became known as "pyroxylic spirit". In 1834, the French chemists Jean-Baptiste Dumas and Eugene Peligot determined its elemental composition.[28]

They also introduced the word "methylène" to organic chemistry, forming it from Greek methy = "alcoholic liquid" + hȳlē = "forest, wood, timber, material". "Methylène" designated a "radical" that was about 14% hydrogen by weight and contained one carbon atom. This would be CH2, but at the time carbon was thought to have an atomic weight only six times that of hydrogen, so they gave the formula as CH.[28] They then called wood alcohol (l'esprit de bois) "bihydrate de méthylène" (bihydrate because they thought the formula was C4H8O4 or (CH)4(H2O)2). The term "methyl" was derived in about 1840 by back-formation from "methylene", and was then applied to describe "methyl alcohol". This was shortened to "methanol" in 1892 by the International Conference on Chemical Nomenclature.[29] The suffix -yl, which, in organic chemistry, forms names of carbon groups, is from the word methyl.

French chemist Paul Sabatier presented the first process that could be used to produce methanol synthetically in 1905. This process suggested that carbon dioxide and hydrogen could be reacted to produce methanol.[9] German chemists Alwin Mittasch and Mathias Pier, working for Badische-Anilin & Soda-Fabrik (BASF), developed a means to convert synthesis gas (a mixture of carbon monoxide, carbon dioxide, and hydrogen) into methanol and received a patent. According to Bozzano and Manenti, BASF's process was first utilized in Leuna, Germany in 1923. Operating conditions consisted of "high" temperatures (between 300 and 400 °C) and pressures (between 250 and 350 atm) with a zinc/chromium oxide catalyst.[30]

US patent 1,569,775 was applied for on 4 September 1924 and issued on 12 January 1926 to BASF;[31] the process used a chromium and manganese oxide catalyst with extremely vigorous conditions: pressures ranging from 50 to 220 atm, and temperatures up to 450 °C. Modern methanol production has been made more efficient through use of catalysts (commonly copper) capable of operating at lower pressures. The modern low pressure methanol (LPM) process was developed by ICI in the late 1960s with the technology patent long since expired.[32]

During World War II, methanol was used as a fuel in several German military rocket designs, under the name M-Stoff, and in a roughly 50/50 mixture with hydrazine, known as C-Stoff.

The use of methanol as a motor fuel received attention during the oil crises of the 1970s. By the mid-1990s, over 20,000 methanol flexible fuel vehicles (FFVs) capable of operating on methanol or gasoline were introduced in the US. In addition, low levels of methanol were blended in gasoline fuels sold in Europe during much of the 1980s and early-1990s. Automakers stopped building methanol FFVs by the late-1990s, switching their attention to ethanol-fueled vehicles. While the methanol FFV program was a technical success, rising methanol pricing in the mid- to late-1990s during a period of slumping gasoline pump prices diminished interest in methanol fuels.[33]

In the early 1970s, a process was developed by Mobil for producing gasoline fuel from methanol.[34]

Between the 1960s and 1980s methanol emerged as a precursor to the feedstock chemicals acetic acid and acetic anhydride. These processes include the Monsanto acetic acid synthesis, Cativa process, and Tennessee Eastman acetic anhydride process.

## Applications

[edit]

### Production of formaldehyde, acetic acid, methyl tert-butyl ether

[edit]

Methanol is primarily converted to formaldehyde, which is widely used in many areas, especially polymers. The conversion entails oxidation:

2 CH3OH + O2 → 2 CH2O + 2 H2O

Acetic acid can be produced from methanol.

The Cativa process converts methanol into acetic acid.[35]

Methanol and isobutene are combined to give methyl tert-butyl ether (MTBE). MTBE is a major octane booster in gasoline.

### Methanol to hydrocarbons, olefins, gasoline

[edit]

Condensation of methanol to produce hydrocarbons and even aromatic systems is the basis of several technologies related to gas to liquids. These include methanol-to-hydrocarbons (MtH), methanol to gasoline (MtG), methanol to olefins (MtO), and methanol to propylene (MtP). These conversions are catalyzed by zeolites as heterogeneous catalysts. The MtG process was once commercialized at Motunui in New Zealand.[36][37]

### Gasoline additive

[edit]

The European Fuel Quality Directive allows fuel producers to blend up to 3% methanol, with an equal amount of cosolvent, with gasoline sold in Europe. In 2019, it is estimated that China used as much as 7 million tons of methanol as transportation fuels, representing over 5% of their fuel pool.[38]

### Other chemicals

[edit]

Methanol is the precursor to most simple methylamines, methyl halides, and methyl ethers.[18] Methyl esters are produced from methanol, including the transesterification of fats and production of biodiesel via transesterification.[39][40]

### Niche and potential uses

[edit]

#### Energy carrier

[edit]

Methanol is a promising energy carrier because, as a liquid, it is easier to store than hydrogen and natural gas. Its energy density is, however, lower than methane, per kg. Its combustion energy density is 15.6 MJ/L (LHV), whereas that of ethanol is 24 and gasoline is 33 MJ/L.

Further advantages for methanol is its ready biodegradability and low environmental toxicity. It does not persist in either aerobic (oxygen-present) or anaerobic (oxygen-absent) environments. The half-life for methanol in groundwater is just one to seven days, while many common gasoline components have half-lives in the hundreds of days (such as benzene at 10–730 days). Since methanol is miscible with water and biodegradable, it is unlikely to accumulate in groundwater, surface water, air or soil.[41]

#### Fuel

[edit]

Main articles: Methanol fuel and methanol economy

Methanol is occasionally used to fuel internal combustion engines. It burns forming carbon dioxide and water:

2 CH3OH + 3 O2 → 2 CO2 \+ 4 H2O

Methanol fuel has been proposed for ground transportation. The chief advantage of a methanol economy is that it could be adapted to gasoline internal combustion engines with minimum modification to the engines and to the infrastructure that delivers and stores liquid fuel. Its energy density, however, is less than gasoline, meaning more frequent fill ups would be required. However, it is equivalent to super high-octane gasoline in horsepower, and most modern computer-controlled fuel injection systems can already use it.[42]

Methanol is an alternative fuel for ships that helps the shipping industry meet increasingly strict emissions regulations. It significantly reduces emissions of sulfur oxides (SOx), nitrogen oxides (NOx) and particulate matter. Methanol can be used with high efficiency in marine diesel engines after minor modifications using a small amount of pilot fuel (dual fuel).[43][44]

In China, methanol fuels industrial boilers, which are used extensively to generate heat and steam for various industrial applications and residential heating. Its use is displacing coal, which is under pressure from increasingly stringent environmental regulations.[45]

Direct-methanol fuel cells are unique in their low temperature, atmospheric pressure operation, which lets them be greatly miniaturized.[46][47] This, combined with the relatively easy and safe storage and handling of methanol, may open the possibility of fuel cell-powered consumer electronics, such as laptop computers and mobile phones.[48]

Methanol is also a widely used fuel in camping and boating stoves. Methanol burns well in an unpressurized burner, so alcohol stoves are often very simple, sometimes little more than a cup to hold fuel. This lack of complexity makes them a favorite of hikers who spend extended time in the wilderness. Similarly, the alcohol can be gelled to reduce risk of leaking or spilling, as with the brand "Sterno".

Methanol is mixed with water and injected into high performance diesel and gasoline engines for an increase of power and a decrease in intake air temperature in a process known as water methanol injection.

#### Other applications

[edit]

Methanol is used as a denaturant for ethanol, the product being known as denatured alcohol or methylated spirit. This was commonly used during the US prohibition to discourage consumption of bootlegged liquor, and ended up causing several deaths.[49]

It is sometimes used as a fuel in alcohol lamps, portable fire pits and camping stoves.

Methanol is used as a solvent and as an antifreeze in pipelines and windshield washer fluid. Methanol was used as an automobile coolant antifreeze in the early 1900s.[50] As of May 2018, methanol was banned in the EU for use in windscreen washing or defrosting due to its risk of human consumption[51][52] as a result of 2012 Czech Republic methanol poisonings.[53]

In some wastewater treatment plants, a small amount of methanol is added to wastewater to provide a carbon food source for the denitrifying bacteria, which convert nitrates to nitrogen gas and reduce the nitrification of sensitive aquifers.

Methanol is used as a destaining agent in polyacrylamide gel electrophoresis.

## Production

[edit]

### From synthesis gas

[edit]

Carbon monoxide and hydrogen react over a catalyst to produce methanol. Today, the most widely used catalyst is a mixture of copper and zinc oxides, supported on alumina, as first used by ICI in 1966. At 5–10 MPa (50–100 atm) and 250 °C (482 °F), the reaction

CO + 2 H2 → CH3OH

is characterized by high selectivity (>99.8%). The production of synthesis gas from methane produces three moles of hydrogen for every mole of carbon monoxide, whereas the synthesis consumes only two moles of hydrogen gas per mole of carbon monoxide. One way of dealing with the excess hydrogen is to inject carbon dioxide into the methanol synthesis reactor, where it, too, reacts to form methanol according to the equation

CO2 \+ 3 H2 → CH3OH + H2O

In terms of mechanism, the process occurs via initial conversion of CO into CO2, which is then hydrogenated:[54]

CO2 \+ 3 H2 → CH3OH + H2O

where the H2O byproduct is recycled via the water-gas shift reaction

CO + H2O → CO2 \+ H2

This gives an overall reaction

CO + 2 H2 → CH3OH

which is the same as listed above. In a process closely related to methanol production from synthesis gas, a feed of hydrogen and CO2 can be used directly.[55] The main advantage of this process is that captured CO2 and hydrogen sourced from electrolysis could be used, removing the dependence on fossil fuels.

### Biosynthesis

[edit]

The catalytic conversion of methane to methanol is effected by enzymes including methane monooxygenases. These enzymes are mixed-function oxygenases, i.e. oxygenation is coupled with production of water[56] and NAD+:[57]

CH4 \+ O2 \+ NADPH + H+ → CH3OH + H2O + NAD+

Both Fe- and Cu-dependent enzymes have been characterized.[57] Intense but largely fruitless efforts have been undertaken to emulate this reactivity.[58][59] Methanol is more easily oxidized than is the feedstock methane, so the reactions tend not to be selective. Some strategies exist to circumvent this problem. Examples include Shilov systems and Fe- and Cu-containing zeolites.[60] These systems do not necessarily mimic the mechanisms employed by metalloenzymes, but draw some inspiration from them. Active sites can vary substantially from those known in the enzymes. For example, a dinuclear active site is proposed in the sMMO enzyme, whereas a mononuclear iron (alpha-oxygen) is proposed in the Fe-zeolite.[61]

Global emissions of methanol by plants are estimated at between 180 and 250 million tons per year.[62] This is between two and three times larger than man-made industrial production of methanol.

## Green methanol

[edit]

As of 2023, 0.2% of global methanol production is produced in ways that have relatively low greenhouse gas emissions; this is known as "green" methanol.[63] Most green methanol is produced from gasification of biomass.[63] Syngas is produced from biomass gasification and further converted into green methanol.[64]

Another method of producing green methanol involves combining hydrogen, carbon dioxide, and a catalyst under high heat and pressure.[63] To be classified as green methanol, the hydrogen must be green hydrogen, which is produced using renewable electricity.[63] Additionally, the carbon dioxide in this process must be a product of carbon capture and storage or direct air capture or biomass of recent origin.[63] Some definitions of green methanol specify that the carbon dioxide must be captured during the burning of bioenergy.[65]

## Quality specifications and analysis

[edit]

Methanol is available commercially in various purity grades. Commercial methanol is generally classified according to ASTM purity grades A and AA. Both grade A and grade AA purity are 99.85% methanol by weight. Grade "AA" methanol contains trace amounts of ethanol as well.[30]

Methanol for chemical use normally corresponds to Grade AA. In addition to water, typical impurities include acetone and ethanol (which are very difficult to separate by distillation). UV-vis spectroscopy is a convenient method for detecting aromatic impurities. Water content can be determined by the Karl-Fischer titration.

## Safety

[edit]

Methanol is highly flammable. Its vapours are slightly heavier than air and can travel to a distant ignition source and ignite. Methanol fires should be extinguished with dry chemical, carbon dioxide, water spray or alcohol-resistant foam.[12] Methanol flames are invisible in daylight.

### Toxicity

[edit]

Main article: Methanol toxicity

See also: List of methanol poisoning incidents

Ingesting as little as 10 mL (0.34 US fl oz) of pure methanol can cause permanent blindness by destruction of the optic nerve. 30 mL (1.0 US fl oz) is potentially fatal.[66] The median lethal dose is 100 mL (3.4 US fl oz), i.e., 1–2 mL/kg body weight of pure methanol.[67] The reference dose for methanol is 0.5 mg/kg in a day.[68][69] Toxic effects begin hours after ingestion, and antidotes can often prevent permanent damage.[66] Because of its similarities in both appearance and odor to ethanol (the alcohol in beverages) or isopropyl alcohol, it is difficult to differentiate between the three.[70]

Methanol is toxic by two mechanisms. First, methanol can be fatal due to effects on the central nervous system, acting as a central nervous system depressant in the same manner as ethanol poisoning. Second, in a process of toxication, it is metabolised to formic acid (which is present as the formate ion) via formaldehyde in a process initiated by the enzyme alcohol dehydrogenase in the liver.[71] Methanol is converted to formaldehyde via alcohol dehydrogenase (ADH) and formaldehyde is converted to formic acid (formate) via aldehyde dehydrogenase (ALDH). The conversion to formate via ALDH proceeds completely, with no detectable formaldehyde remaining.[72] Formate is toxic because it inhibits mitochondrial cytochrome c oxidase, causing hypoxia at the cellular level, and metabolic acidosis, among a variety of other metabolic disturbances.[73]

Outbreaks of methanol poisoning have occurred primarily due to contamination of drinking alcohol. It is also worth noting that ethanol is a natural antidote to methanol poisoning. [74] Contaminated batches of alcohol contained a much higher concentration of methanol than ethanol, which did not provide a sufficient dose of the antidote and caused it to be ineffective. This is more common in the developing world.[75] In 2013 more than 1700 cases nonetheless occurred in the United States. Those affected are often adult men.[76] Outcomes may be good with early treatment.[77] Toxicity to methanol was described as early as 1856.[78]

Because of its toxic properties, methanol is frequently used as a denaturant additive for ethanol manufactured for industrial uses. This addition of methanol exempts industrial ethanol (commonly known as "denatured alcohol" or "methylated spirit") from liquor excise taxation in the US and other countries.

## See also

[edit]

* Aminomethanol
* Methanol (data page)
* Trimethyl carbinol

## References

[edit]

1. ^ Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 692\. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
2. ^ Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton, Florida: CRC Press. ISBN 0-8493-0486-5.
3. ^ Ballinger, P.; Long, F. A. (1960). "Acid Ionization Constants of Alcohols. II. Acidities of Some Substituted Methanols and Related Compounds". J. Am. Chem. Soc. 82 (4): 795–798\. Bibcode:1960JAChS..82..795B. doi:10.1021/ja01489a008.795-798&rft.date=1960&rft_id=info:doi/10.1021/ja01489a008&rft_id=info:bibcode/1960JAChS..82..795B&rft.aulast=Ballinger&rft.aufirst=P.&rft.au=Long,+F.+A.&rfr_id=info:sid/en.wikipedia.org:Methanol" class="Z3988">
4. ^ "Methyloxonium". pubchem.ncbi.nlm.nih.gov. Archived from the original on 21 December 2018. Retrieved 21 December 2018.
5. ^ "Methanolate". pubchem.ncbi.nlm.nih.gov. Archived from the original on 21 December 2018. Retrieved 21 December 2018. "Methoxide is an organic anion that is the conjugate base of methanol. ... It is a conjugate base of a methanol."
6. ^ "RefractiveIndex.INFO – Refractive index database". refractiveindex.info. Archived from the original on 23 February 2017. Retrieved 14 February 2012.
7. ^ González, Begoña (2007). "Density, dynamic viscosity, and derived properties of binary mixtures of methanol or ethanol with water, ethyl acetate, and methyl acetate at T = (293.15, 298.15, and 303.15) K". The Journal of Chemical Thermodynamics. 39 (12): 1578–1588\. Bibcode:2007JChTh..39.1578G. doi:10.1016/j.jct.2007.05.004.1578-1588&rft.date=2007&rft_id=info:doi/10.1016/j.jct.2007.05.004&rft_id=info:bibcode/2007JChTh..39.1578G&rft.aulast=González&rft.aufirst=Begoña&rfr_id=info:sid/en.wikipedia.org:Methanol" class="Z3988">
8. ^ a b c d "Methanol" (PDF). Lab Chem. Valtech. Archived (PDF) from the original on 10 March 2016. Retrieved 10 March 2016.
9. ^ a b Toxicity on PubChem Archived 20 August 2018 at the Wayback Machine
10. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0397". National Institute for Occupational Safety and Health (NIOSH).
11. ^ a b c "Methanol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
12. ^ a b c "The Emergency Response Safety and Health Database: Systematic Agent: METHANOL". Centers for Disease Control and Prevention. Archived from the original on 23 April 2009. Retrieved 3 August 2018.
13. ^ "PubChem: Safety and Hazards - GHS Classification". National Center for Biotechnology Information, U.S. National Library of Medicine. Archived from the original on 20 August 2018. Retrieved 20 August 2018.
14. ^ "Methanol Safe Handling Manual" (PDF). Methanol Institute. 2017. p. 253\. Archived (PDF) from the original on 20 December 2017. Retrieved 3 August 2018.
15. ^ "Technical Information & Safe Handling Guide for Methanol". Methanex Corporation. Archived from the original on 11 March 2012.
16. ^ "Methanol Safe Handling Manual" (PDF). Methanol Institute. 2017. p. 243\. Archived (PDF) from the original on 20 December 2017. Retrieved 3 August 2018.
17. ^ National Institute for Occupational Safety and Health (22 August 2008). "The Emergency Response Safety and Health Database: Methanol". Archived from the original on 23 April 2009. Retrieved 17 March 2009.
18. ^ a b c Fiedler, E.; Grossmann, G.; Burkhard Kersebohm, D.; Weiss, G.; Witte, C. (2005). "Methanol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_465. ISBN 978-3-527-30673-2.
19. ^ Turner C (2006). "A longitudinal study of methanol in the exhaled breath of 30 healthy volunteers using selected ion flow tube mass spectrometry, SIFT-MS". Physiological Measurement. 27 (7): 637–48\. Bibcode:2006PhyM...27..637T. doi:10.1088/0967-3334/27/7/007. PMID 16705261. S2CID 22365066.637-48&rft.date=2006&rft_id=info:doi/10.1088/0967-3334/27/7/007&rft_id=https://api.semanticscholar.org/CorpusID:22365066#id-name=S2CID&rft_id=info:pmid/16705261&rft_id=info:bibcode/2006PhyM...27..637T&rft.au=Turner+C&rfr_id=info:sid/en.wikipedia.org:Methanol" class="Z3988">
20. ^ Lindinger W (1997). "Endogenous production of methanol after the consumption of fruit". Alcoholism: Clinical and Experimental Research. 21 (5): 939–43\. doi:10.1111/j.1530-0277.1997.tb03862.x. PMID 9267548.939-43&rft.date=1997&rft_id=info:doi/10.1111/j.1530-0277.1997.tb03862.x&rft_id=info:pmid/9267548&rft.au=Lindinger+W&rfr_id=info:sid/en.wikipedia.org:Methanol" class="Z3988">
21. ^ "Major Source of Methanol in the Ocean Identified". Woods Hole Oceanographic Institution. 10 March 2016. Archived from the original on 28 December 2018. Retrieved 30 March 2016.
22. ^ Mincer, Tracy J.; Aicher, Athena C. (2016). "Methanol Production by a Broad Phylogenetic Array of Marine Phytoplankton". PLOS ONE. 11 (3): e0150820. Bibcode:2016PLoSO..1150820M. doi:10.1371/journal.pone.0150820. PMC 4786210. PMID 26963515.
23. ^ Brooks Hays (17 April 2015). "Why astronomers hate the lawn-mowing Roomba". Space Daily. Archived from the original on 27 April 2015. Retrieved 20 April 2015.
24. ^ "Upgraded MERLIN spies cloud of alcohol spanning 288 billion miles" (Press release). Jodrell Bank Centre for Astrophysics. 19 April 2006. Archived from the original on 20 July 2011.
25. ^ Amos, Jonathan (5 April 2006). "Merlin sees vast alcohol stream". BBC News. Archived from the original on 6 October 2014. Retrieved 5 September 2010.
26. ^ "First Detection of Methyl Alcohol in a Planet-forming Disc". Archived from the original on 22 June 2016. Retrieved 22 June 2016.
27. ^ Boyle discusses the distillation of liquids from the wood of the box shrub in: Robert Boyle, The Sceptical Chymist (London, England: J. Cadwell, 1661), pp. 192–195.
28. ^ a b A report on methanol to the French Academy of Sciences by J. Dumas and E. Péligot began during the Academy's meeting of 27 October 1834 and finished during the meeting of 3 November 1834. See: Procès-verbaux des séances de l'Académie, 10 : 600–601. Available on: Gallica Archived 25 April 2015 at the Wayback Machine. The complete report appears in: J. Dumas and E. Péligot (1835) "Mémoire sur l'espirit de bois et sur les divers composés ethérés qui en proviennent" (Memoir on spirit of wood and on the various ethereal compounds that derive therefrom), Annales de chimie et de physique, 58 : 5–74; from page 9: Nous donnerons le nom de méthylène (1) à un radical ... (1) Μεθυ, vin, et υλη, bois; c'est-à-dire vin ou liqueur spiritueuse du bois. (We will give the name methylene (1) to a radical ... (1) methy, wine, and hulē, wood; that is, wine or spirit of wood.)
29. ^ For a report on the International Conference on Chemical Nomenclature that was held in April 1892 in Geneva, Switzerland, see:
* Armstrong, Henry E (1892). "The International Conference on Chemical Nomenclature". Nature. 46 (1177): 56–9\. Bibcode:1892Natur..46...56A. doi:10.1038/046056c0.56-9&rft.date=1892&rft_id=info:doi/10.1038/046056c0&rft_id=info:bibcode/1892Natur..46...56A&rft.aulast=Armstrong&rft.aufirst=Henry+E&rft_id=https://books.google.com/books?id=LHkCAAAAIAAJ&pg;=PA5&rfr_id=info:sid/en.wikipedia.org:Methanol" class="Z3988">
* Armstrong's report is reprinted with the resolutions in English in: Armstrong, Henry (1892). "The International Conference on Chemical Nomenclature". The Journal of Analytical and Applied Chemistry. 6 (1177): 390–400\. Bibcode:1892Natur..46...56A. doi:10.1038/046056c0. "p. 398: 15. The alcohols and the phenols are named after the hydrocarbon from which they derive, terminated with the suffix ol (ex. pentanol, pentenol, etc.)."390-400&rft.date=1892&rft_id=info:doi/10.1038/046056c0&rft_id=info:bibcode/1892Natur..46...56A&rft.au=Armstrong,+Henry&rft_id=https://books.google.com/books?id=RogMAQAAIAAJ&pg;=PA398&rfr_id=info:sid/en.wikipedia.org:Methanol" class="Z3988">
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## Further reading

[edit]

* Robert Boyle, The Sceptical Chymist (1661) – contains account of distillation of wood alcohol.
* Schmidt, Eckart W. (2022). "Methanol". Alcohols. Encyclopedia of Liquid Fuels. De Gruyter. pp. 2–12\. doi:10.1515/9783110750287-001. ISBN 978-3-11-075028-7.2-12&rft.pub=De+Gruyter&rft.date=2022&rft_id=info:doi/10.1515/9783110750287-001&rft.isbn=978-3-11-075028-7&rft.aulast=Schmidt&rft.aufirst=Eckart+W.&rfr_id=info:sid/en.wikipedia.org:Methanol" class="Z3988">

## External links

[edit]

* International Chemical Safety Card 0057
* Methyl Alcohol (Methanol) CDC/NIOSH, links to safety information
* CDC – NIOSH Pocket Guide to Chemical Hazards – Methyl Alcohol
* Methanol Fact Sheet – National Pollutant Inventory

* v
* t
* e

Alcohols

By consumption|

| Alcohols found in
alcoholic drinks|

* 1-Propanol
* 2-Methyl-1-butanol
* Ethanol
* Isoamyl alcohol
* Isobutanol
* Phenethyl alcohol
* tert-Amyl alcohol
* tert-Butyl alcohol
* Tryptophol

|

Medical alcohol|

* Ethchlorvynol
* Methylpentynol
* Methanol poisoning
* Ethanol

Toxic alcohols|

* Isopropyl alcohol
* Methanol

Primary
alcohols (1°)|

| Methanol|

* 4-Methylcyclohexanemethanol
* Aminomethanol
* Cyclohexylmethanol
* Methoxymethanol
* Methylazoxymethanol
* Trifluoromethanol

|

Ethanol|

* 1-Aminoethanol
* 2,2,2-Trichloroethanol
* 2,2,2-Trifluoroethanol
* 2-(2-Ethoxyethoxy)ethanol
* 2-(2-Methoxyethoxy)ethanol
* 2-(2-Methoxyethoxy)ethanol
* 2-Butoxyethanol
* 2-Chloroethanol
* 2-Ethoxyethanol
* 2-Fluoroethanol
* 2-Mercaptoethanol
* 2-Methoxyethanol
* Aminoethylethanolamine
* Diethylethanolamine
* Dimethylethanolamine
* Ethanol
* Ethanolamine
* N,N-Diisopropylaminoethanol
* N-Methylethanolamine
* Phenoxyethanol
* Tribromoethanol

Butanol|

* 2-Methyl-1-butanol
* Isobutanol
* n-Butanol

Straight-chain
saturated
C1 — C9|

* Methanol
* Ethanol
* 1-Propanol
* 1-Butanol
* 1-Pentanol
* 1-Hexanol
* 1-Heptanol
* 1-Octanol (capryl)
* 1-Nonanol (pelargonic)

Straight-chain
saturated
C10 — C19|

* 1-Decanol (capric)
* 1-Undecanol (hendecyl)
* 1-Dodecanol (lauryl)
* 1-Tridecanol
* 1-Tetradecanol (myristyl)
* 1-Pentadecanol
* 1-Hexadecanol (cetyl / palmityl)
* 1-Heptadecanol
* 1-Octadecanol (stearyl)
* 1-Nonadecanol

Straight-chain
saturated
C20 — C29|

* 1-Icosanol (arachidyl)
* 1-Heneicosanol
* 1-Docosanol (behenyl)
* 1-Tricosanol
* 1-Tetracosanol (lignoceryl)
* 1-Pentacosanol
* 1-Hexacosanol (ceryl)
* 1-Heptacosanol
* 1-Octacosanol (cluytyl / montanyl)
* 1-Nonacosanol

Straight-chain
saturated
C30 — C39|

* 1-Triacontanol (melissyl / myricyl)
* 1-Hentriacontanol
* 1-Dotriacontanol (lacceryl)
* 1-Tritriacontanol
* 1-Tetratriacontanol (geddyl)
* 1-Pentatriacontanol
* 1-Hexatriacontanol
* 1-Heptatriacontanol
* 1-Octatriacontanol
* 1-Nonatriacontanol

Straight-chain
saturated
C40 — C49|

* 1-Tetracontanol
* 1-Hentetracontanol
* 1-Dotetracontanol
* 1-Tritetracontanol
* 1-Tetratetracontanol
* 1-Pentatetracontanol
* 1-Hexatetracontanol
* 1-Heptatetracontanol
* 1-Octatetracontanol
* 1-Nonatetracontanol

* 2-Ethylhexanol
* Allyl alcohol
* Anisyl alcohol
* Benzyl alcohol
* Cinnamyl alcohol
* Crotyl alcohol
* Furfuryl alcohol
* Isoamyl alcohol
* Neopentyl alcohol
* Nicotinyl alcohol
* Perillyl alcohol
* Phenethyl alcohol
* Prenol
* Propargyl alcohol
* Salicyl alcohol
* Tryptophol
* Vanillyl alcohol
* Veratrole alcohol

Secondary
alcohols (2°)|

* 1-Phenylethanol
* 2-Butanol
* 2-Deoxyerythritol
* 2-Heptanol
* 3-Heptanol
* 2-Hexanol
* 3-Hexanol
* 3-Methyl-2-butanol
* 2-Nonanol
* 2-Octanol
* 2-Pentanol
* 3-Pentanol
* Cyclohexanol
* Cyclopentanol
* Cyclopropanol
* Diphenylmethanol
* Isopropanol
* Pinacolyl alcohol
* Pirkle's alcohol
* Propylene glycol methyl ether

Tertiary
alcohols (3°)|

* 2-Methyl-2-pentanol
* 2-Methylheptan-2-ol
* 2-Methylhexan-2-ol
* 3-Methyl-3-pentanol
* 3-Methyloctan-3-ol
* Diacetone alcohol
* Ethchlorvynol
* Methylpentynol
* Nonafluoro-tert-butyl alcohol
* tert-Amyl alcohol
* tert-Butyl alcohol
* Triphenylethanol
* Triphenylmethanol

Hydric alcohols|

| Monohydric alcohols|

* Methanol (C1)
* Ethanol (C2)
* Isopropanol (C3)
* 1-Butanol (C4)
* 1-Pentanol (C5)
* Cetyl alcohol (C16)

|

Dihydric alcohols|

* Ethylene glycol
* Propylene glycol

Trihydric alcohols|

* Glycerol

Polyhydric alcohols (sugar alcohols)|

* Pentaerythritol
* Ethylene glycol (C2)
* Glycerol, Propylene glycol (C3)
* Erythritol, Threitol (C4)
* Xylitol (C5)
* Mannitol, Sorbitol (C6)
* Volemitol (C7)

Amyl alcohols|

* 2,2-Dimethylpropan-1-ol
* 2-Methylbutan-1-ol
* 2-Methylbutan-2-ol
* 3-Methylbutan-1-ol
* 3-Methylbutan-2-ol
* Pentan-1-ol
* Pentan-2-ol
* Pentan-3-ol

Aromatic alcohols|

* Benzyl alcohol
* 2,4-Dichlorobenzyl alcohol
* 3-Nitrobenzyl alcohol

Saturated
fatty alcohols|

* Cetostearyl alcohol
* Decanol
* Lauryl alcohol
* Myristyl alcohol
* Nonanol
* Octanol
* Tridecanol
* Undecanol

Branched and
unsaturated
fatty alcohols|

* 3-Methyl-3-pentanol
* Erucyl alcohol
* Linolenyl alcohol
* Linoleyl alcohol
* Oleyl alcohol
* Palmitoleyl alcohol
* tert-Amyl alcohol
* tert-Butyl alcohol

Sugar alcohols|

| C1 — C7|

* Methylene glycol (C1)
* Ethylene glycol (C2)
* Glycerol (C3)
* Erythritol (C4)
* Threitol (C4)
* Arabitol (C5)
* Ribitol (C5)
* Xylitol (C5)
* Mannitol (C6)
* Sorbitol (C6)
* Galactitol (C6)
* Iditol (C6)
* Volemitol (C7)

|

Deoxy sugar
alcohols|

* Fucitol

Cyclic sugar
alcohols|

* Inositol

Glycylglycitols|

* Maltitol
* Lactitol
* Isomalt
* Maltotriitol
* Maltotetraitol
* Polyglycitol

Terpene alcohols|

| Monoterpene
alcohols|

* Borneol
* Citronellol
* Geraniol
* Linalool
* Menthol
* Nerol
* Rhodinol
* Terpineol

|

Sesquiterpene
alcohols|

* Bisabolol
* Farnesol
* Nerolidol
* Patchoulol

Diterpene
alcohols|

* Phytol

Dialcohols|

* 1,4-Butanediol
* 1,5-Pentanediol
* 2-Methyl-2-propyl-1,3-propanediol
* Diethylpropanediol
* Ethylene glycol

Trialcohols|

* Glycerol

Sterols|

* Cholesterol
* Ergosterol
* Lanosterol
* β-Sitosterol
* Stigmasterol

Fluoroalcohols|

* 1,3-Difluoro-2-propanol
* 2,2,2-Trifluoroethanol
* 2-Fluoroethanol
* Nonafluoro-tert-butyl alcohol
* Trifluoromethanol

Preparations|

* Substitution of haloalkane
* Carbonyl reduction
* Ether cleavage
* Hydrolysis of epoxide
* Hydration of alkene
* Ziegler process

Reactions|

* Deprotonation
* Protonation
* Alcohol oxidation
* Glycol cleavage
* Nucleophilic substitution
* Fischer–Speier esterification
* Williamson ether synthesis
* Elimination reaction
* Nucleophilic substitution of carbonyl group
* Friedel-Crafts alkylation
* Nucleophilic conjugate addition
* Transesterification

* Category

* v
* t
* e

Neurotoxins

Animal toxins|

* Batrachotoxin
* Bestoxin
* Birtoxin
* Bungarotoxin
* Charybdotoxin
* Conotoxin
* Fasciculin
* Huwentoxin
* Poneratoxin
* Saxitoxin
* Tetrodotoxin
* Vanillotoxin
* Spooky toxin (SsTx)
* Epibatidine
* Zetekitoxin AB
* Dendrotoxin

Bacterial|

* Botulinum toxin
* Tetanospasmin

Cyanotoxins|

* Anatoxin-a
* Guanitoxin
* BMAA
* Saxitoxin

Plant toxins|

* Aconitine
* Bicuculline
* Penitrem A
* Picrotoxin
* Strychnine
* Tutin
* Rotenone
* Ginkgotoxin
* Cicutoxin
* Oenanthotoxin
* Thujone
* Volkensin
* Veratridine

Mycotoxins|

* Ibotenic acid
* Muscarine
* Muscimol

Pesticides|

* Fenpropathrin
* Tetramethylenedisulfotetramine
* Bromethalin
* Crimidine
* Methamidophos
* Endosulfan
* Fipronil
* Phenylsilatrane
* Chlorophenylsilatrane
* Sulfuryl fluoride
* Mipafox
* Schradan
* Dimefox

Nerve agents|

* Cyclosarin
* EA-3148
* Novichok agent
* Sarin
* Soman
* Tabun
* VE
* VG
* VM
* VP
* VR
* VX
* GV
* EA-3990
* EA-4056
* T-1123
* Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)
* Fluorotabun
* Chinese VX
* EA-2192

Bicyclic phosphates|

* TBPS
* TBPO
* IPTBO

Cholinergic neurotoxins|

* Acetylcholine mustard
* Catecholine
* Choline mustard
* Ethylcholine mustard
* Hemicholinium mustard

Psychoactive drugs|

* Alcohol
* Nitrous oxide

Other|

* Dimethylcadmium
* Dimethylmercury
* Toxopyrimidine
* IDPN
* Tetraethyllead

* v
* t
* e

Wood products

Lumber/
timber|

* Batten
* Beam
* Bressummer
* CLS
* Cruck
* Flitch beam
* Flooring
* Joist
* Lath
* Log building
* Log cabin
* Log house
* Molding
* Panelling
* Plank
* Plate
* Post
* Purlin
* Rafter
* Railroad ties
* Reclaimed
* Shingle
* Siding
* Sill
* Stud
* Timber truss
* Treenail
* Truss
* Utility pole

Engineered
wood|

* Cross-laminated timber
* Glued laminated timber
* veneer
* LVL
* parallel strand
* I-joist
* Fiberboard
* hardboard
* Masonite
* MDF
* Oriented strand board
* Oriented structural straw board
* Particle board
* Plywood
* Structural insulated panel
* Wood–plastic composite
* lumber

Fuelwood|

* Charcoal
* biochar
* Firelog
* Firewood
* Pellet fuel
* Wood fuel

Fibers|

* Cardboard
* Corrugated fiberboard
* Paper
* Paperboard
* Pulp
* Pulpwood
* Rayon

Derivatives|

* Birch-tar
* Cellulose
* nano
* Hemicellulose
* Cellulosic ethanol
* Dyes
* Lignin
* Liquid smoke
* Lye
* Methanol
* Pyroligneous acid
* Pine tar
* Pitch
* Sandalwood oil
* Tannin
* Wood gas

By-products|

* Barkdust
* Black liquor
* Ramial chipped wood
* Sawdust
* Tall oil
* Wood flour
* Wood wool
* Woodchips

Historical|

* Axe ties
* Bavin (wood)
* Billet (wood)
* Clapboard
* Dugout canoe
* Potash
* Sawdust brandy
* Split-rail fence
* Tanbark
* Timber framing
* Wooden masts

See also|

* Biomass
* Certified wood
* Destructive distillation
* Dry distillation
* Engineered bamboo
* Forestry
* Green building and wood
* List of woods
* Mulch
* Non-timber forest products
* Natural building
* Papermaking
* Reclaimed lumber
* Timber recycling
* Wood drying
* Wood preservation
* Wood processing
* Woodworking
* Yakisugi

* Category
* Commons
* WikiProject Forestry

* 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
* Imidogen
* Iron(II) oxide
* Magnesium monohydride
* Methylidyne radical
* Nitric oxide
* Nitrogen (molecular)
* Oxygen (molecular)
* Phosphorus monoxide
* Phosphorus mononitride
* Potassium chloride
* Silicon carbide
* Silicon monoxide
* Silicon monosulfide
* Sodium chloride
* Sodium iodide
* Sulfanyl
* Sulfur mononitride
* 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
* Methylidynephosphane
* N2H+
* Nitrous oxide
* Nitroxyl
* Ozone
* Potassium cyanide
* Sodium cyanide
* Sodium hydroxide
* Silicon carbonitride
* c-Silicon dicarbide
* SiNC
* Sulfur dioxide
* Thioformyl
* Thioxoethenylidene
* Titanium dioxide
* Tricarbon
* Trihydrogen cation
* Water

Four
atoms|

* Acetylene
* Ammonia
* Cyanoethynyl
* Formaldehyde
* Fulminic acid
* HCCN
* Hydrogen peroxide
* Hydromagnesium isocyanide
* Isocyanic acid
* Isothiocyanic acid
* Ketenyl
* Methyl cation
* Methyl radical
* Methylene amidogen
* Propynylidyne
* Protonated carbon dioxide
* Protonated hydrogen cyanide
* Silicon tricarbide
* Thiocyanic acid
* Thioformaldehyde
* Tricarbon monosulfide
* Tricarbon monoxide

Five
atoms|

* Ammonium ion
* Butadiynyl
* Carbodiimide
* Cyanamide
* Cyanoacetylene
* Cyanoformaldehyde
* Cyanomethyl
* Cyclopropenylidene
* Formic acid
* Isocyanoacetylene
* Ketene
* Methane
* Methoxy radical
* Methylenimine
* Propadienylidene
* Protonated formaldehyde
* Silane
* Silicon-carbide cluster

Six
atoms|

* Acetonitrile
* Cyanobutadiynyl radical
* Cyclopropenone
* Diacetylene
* E-Cyanomethanimine
* Ethylene
* Formamide
* HC4N
* Ketenimine
* Methanethiol
* Methanol
* Methyl isocyanide
* Pentynylidyne
* Propynal
* Protonated cyanoacetylene

Seven
atoms|

* Acetaldehyde
* Acrylonitrile
* Vinyl cyanide
* Cyanodiacetylene
* Ethylene oxide
* Glycolonitrile
* Hexatriynyl radical
* Methyl isocyanate
* Methylamine
* Propyne
* Vinyl alcohol

Eight
atoms|

* Acetic acid
* Acrolein
* Aminoacetonitrile
* Cyanoallene
* Ethanimine
* Glycolaldehyde
* Hexapentaenylidene
* Methyl formate
* Methylcyanoacetylene

Nine
atoms|

* Acetamide
* Cyanohexatriyne
* Dimethyl ether
* Ethanethiol
* Ethanol
* Methyldiacetylene
* N-Methylformamide
* Octatetraynyl radical
* Propene
* Propionitrile

Ten
atoms
or more|

* Acetone
* Benzene
* Benzonitrile
* Buckminsterfullerene (C60, C60+, fullerene, buckyball)
* Butyronitrile
* C70 fullerene
* Cyanodecapentayne
* Ethyl formate
* Ethylene glycol
* Heptatrienyl radical
* Methyl acetate
* Methyl-cyano-diacetylene
* Methyltriacetylene
* Propionaldehyde
* Pyrimidine

Deuterated
molecules|

* Ammonia
* Ammonium ion
* Formaldehyde
* Formyl radical
* Heavy water
* Hydrogen cyanide
* Hydrogen deuteride
* Hydrogen isocyanide
* N2D+
* Propyne
* Trihydrogen cation

Unconfirmed|

* Anthracene
* Dihydroxyacetone
* Glycine
* Graphene
* H2NCO+
* Hemolithin
* Linear C5
* Methoxyethane
* 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
* Iron–sulfur world theory
* Kerogen
* Molecules in stars
* Nexus for Exoplanet System Science
* Organic compound
* Outer space
* PAH world hypothesis
* Photodissociation region
* Polycyclic aromatic hydrocarbon (PAH)
* Pseudo-panspermia
* RNA world hypothesis
* Spectroscopy
* Tholin

* Category:Astrochemistry
* Outer space portal
* Astronomy portal
* Chemistry portal

* 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
* Nicotinic acid
* Nicotinamide
* 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

Authority control databases: National |

* Germany
* United States
* France
* BnF data
* Japan
* Czech Republic
* Israel

|

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H225]: H225: Highly flammable liquid and vapour
*[H301]: H301: Toxic if swallowed
*[H302]: H302: Harmful if swallowed
*[H305]: H305: May be harmful if swallowed and enters airways
*[H311]: H311: Toxic in contact with skin
*[H331]: H331: Toxic if inhaled
*[H370]: H370: Causes damage to organs
*[P210]: P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.
*[P233]: P233: Keep container tightly closed.
*[P235]: P235: Keep cool.
*[P240]: P240: Ground and bond container and receiving equipment.
*[P241]: P241: Use explosion-proof electrical/ventilating/light/.../equipment.
*[P242]: P242: Use only non-sparking tools.
*[P243]: P243: Take precautionary measures to prevent static discharges.
*[P260]: P260: Do not breathe dust/fume/gas/mist/vapours/spray.
*[P264]: P264: Wash ... thoroughly after handling.
*[P270]: P270: Do not eat, drink or smoke when using this product.
*[P271]: P271: Use only outdoors or in a well-ventilated area.
*[P280]: P280: Wear protective gloves/protective clothing/eye protection/face protection.
*[P301+P330+P331]: P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
*[P302+P352]: P302+P352: IF ON SKIN: Wash with soap and water.
*[P303+P361+P353]: P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].
*[P304+P340]: P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
*[P305+P351+P338]: P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
*[P307+P311]: P307+P311: IF exposed: Call a POISON CENTER or doctor/physician.
*[P310]: P310: Immediately call a POISON CENTER or doctor/physician.
*[P311]: P311: Call a POISON CENTER or doctor/physician.
*[P312]: P312: Call a POISON CENTER or doctor/physician if you feel unwell.
*[P337+P313]: P337+P313: If eye irritation persists: Get medical advice/attention.
*[P361]: P361: Remove/Take off immediately all contaminated clothing.
*[P363]: P363: Wash contaminated clothing before reuse.
*[P370+P378]: P370+P378: In case of fire: Use ... to extinguish.
*[P403+P233]: P403+P233: Store in a well ventilated place. Keep container tightly closed.
*[P405]: P405: Store locked up.
*[P501]: P501: Dispose of contents/container to ...
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*[GABA]: γ-Aminobutyric acid