The Info List - Methanol

Methanol, also known as methyl alcohol among others, is a chemical with the formula CH3OH (often abbreviated MeOH). Methanol
acquired the name wood alcohol because it was once produced chiefly as a byproduct of the destructive distillation of wood. Today, industrial methanol is produced in a catalytic process directly from carbon monoxide, carbon dioxide, and hydrogen. Methanol
is the simplest alcohol, being only a methyl group linked to a hydroxyl group. It is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to that of ethanol (drinking alcohol).[11] However, unlike ethanol, methanol is highly toxic and unfit for consumption. At room temperature, it is a polar liquid. It is used as an antifreeze, solvent, fuel, and as a denaturant for ethanol. It is also used for producing biodiesel by transesterification reaction. Methanol
is produced naturally in the anaerobic metabolism of many varieties of bacteria and is commonly present in small amounts in the environment. As a result, the atmosphere contains a small amount of methanol vapor. However, in only a few days, atmospheric methanol is oxidized by sunlight to produce carbon dioxide and water. 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.[12] Methanol
when drunk is metabolized first to formaldehyde and then to formic acid or formate salts.[13] These are poisonous to the central nervous system and may result in blindness, coma, and death. Because of these 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 some other countries.


1 Occurrence

1.1 Human metabolite

2 Toxicity 3 Applications

3.1 Chemical industry 3.2 Fuel
for vehicles

3.2.1 Usage in the production of biodiesel 3.2.2 Safety in automotive fuels 3.2.3 Government policy

3.3 Production of synthesis gas 3.4 Energy carrier 3.5 Other applications

4 Production

4.1 From synthesis gas 4.2 Biosynthesis

5 Quality specifications and analysis

5.1 Laboratory use 5.2 Commercial methanol

6 History 7 See also 8 References 9 Further reading 10 External links

Occurrence[edit] Human metabolite[edit] Methanol
is poisonous to the central nervous system and may cause blindness, coma, and death. However, in small amounts, methanol is a natural endogenous compound found in normal, healthy human individuals, concluded by one study which found a mean of 4.5 ppm in the exhaled breath of subjects.[14] 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 methanol.[15] Toxicity[edit] Main article: Methanol
toxicity See also: List of methanol poisoning incidents Methanol
has a high toxicity in humans. As little as 10 mL of pure methanol, ingested, is metabolized into formic acid, which can cause permanent blindness by destruction of the optic nerve. 30 mL is potentially fatal,[16] although the median lethal dose is typically 100 mL (3.4 fl oz) (i.e. 1–2 mL/kg body weight of pure methanol[17]). The reference dose for methanol is 2 mg/kg in a day.[18][19] Toxic
effects begin hours after ingestion, and antidotes can often prevent permanent damage.[16] Because of its similarities in both appearance and odor to ethanol (the alcohol in beverages), it is difficult to differentiate between the two (such is also the case with denatured alcohol, adulterated liquors or very low quality alcoholic beverages). However, there are cases of methanol resistance, such as that of Mike Malloy who was the victim of a failed murder attempt by methanol in the early 1930s.[20] Methanol
is toxic by two mechanisms. First, methanol (whether it enters the body by ingestion, inhalation, or absorption through the skin) can be fatal due to its CNS depressant properties in the same manner as ethanol poisoning. Second, in a process of toxication, it is metabolized to formic acid (which is present as the formate ion) via formaldehyde in a process initiated by the enzyme alcohol dehydrogenase in the liver.[21] 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.[22] 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.[23] Outbreaks of methanol poisoning have occurred due to contamination of drinking alcohol. This is more common in the developing world.[24] In 2013 more than 1700 cases occurred in the United States. Those affected are often adult males.[25] Outcomes may be good with early treatment.[26] Toxicity to methanol was described as early as 1856.[27] Applications[edit] Methanol
is used primarily as a feedstock for the manufacture of chemicals, and as a fuel for specialized vehicles. As mentioned above, it is a common denaturing agent. As a common laboratory polar solvent, methanol is especially useful for HPLC, UV/VIS spectroscopy, and LCMS due to its low UV cutoff. Chemical industry[edit] Methanol
is primarily used in making other chemicals. About 40% of methanol is converted to formaldehyde, and from there into products as diverse as plastics, plywood, paints, explosives, and permanent press textiles. Condensation of methanol molecules to produce hydrocarbon chains and even aromatic systems has been demonstrated with loss of water, carbon monoxide, and/or carbon dioxide (loss of oxygen is prohibited on thermodynamic grounds). As early as 1880, an aromatisation reaction which generated hexamethylbenzene as a minor product with a mixture of mostly aliphatic hydrocarbons directly from methanol, using zinc chloride as catalyst, had been demonstrated.[28][29] At 283 °C, the melting point of ZnCl2, the idealised reaction for the production of hexamethylbenzene has a ΔG of −261 kcal mol−1.[28]

15 CH 3OH → C 6(CH 3) 6 + 3 CH 4 + 15 H 2O

In the early 1970s, a process was developed by Mobil
for producing gasoline fuel for vehicles.[28] One such industrial facility was built at Motunui
in New Zealand in the 1980s. In the 1990s, large amounts of methanol were used in the United States to produce the gasoline additive methyl tert-butyl ether (MTBE). While MTBE
is no longer marketed in the U.S., it is still widely used in other parts of the world. Methanol
(or less commonly, ethanol) is a component in the transesterification of triglycerides for production of biodiesel. Other chemical derivatives of methanol include acetic acid and dimethyl ether (DME), the latter of which has replaced chlorofluorocarbons as an aerosol spray propellant. Dimethyl ether
Dimethyl ether
can also be blended with liquified petroleum gas (LPG) for home heating and cooking, and can be used as a replacement for transportation diesel fuel. Of high interest to the petrochemical marketplace, methanol is an important ingredient in new and lower-cost methods for producing propylene, which is much in demand. Such methods include methanol-to-olefins (MTO), methanol-to-propylene (MTO/MTP), metathesis, propane dehydrogenation (PDH), high severity FCC, and olefins cracking. The market for propynyl became tight when the ethane prices fell in the US with the exploration of shale gas reserves. The low priced ethylene produced from this raw material has given chemical producers in North America a feedstock advantage. Such change has put naphtha-fed steam crackers at a disadvantageous position, with many of them shutting down or revamping to use ethane as feedstock. Nevertheless, the propylene output rates from ethane-fed crackers are negligible.[30] Fuel
for vehicles[edit] Main articles: Methanol fuel
Methanol fuel
and methanol economy Methanol
is occasionally used to fuel internal combustion engines. Pure methanol is required by rule to be used in Champcars, Monster Trucks, USAC sprint cars (as well as midgets, modifieds, etc.), and other dirt track series, such as World of Outlaws, and Motorcycle Speedway, mainly because, in the event of an accident, methanol does not produce an opaque cloud of smoke. Since the late 1940s, Methanol is also used as the primary fuel ingredient in the powerplants for radio control, control line, free flight airplanes, cars and trucks; such engines use a platinum filament glow plug that ignites the methanol vapor through a catalytic reaction. Drag racers, mud racers, and heavily modified tractor pullers also use methanol as the primary fuel source. Methanol
is required with a supercharged engine in a Top Alcohol
Dragster and, until the end of the 2006 season, all vehicles in the Indianapolis 500
Indianapolis 500
had to run on methanol. As a fuel for mud racers, methanol mixed with gasoline and nitrous oxide produces more power than gasoline and nitrous oxide alone. Methanol
burns in oxygen, including open air, forming carbon dioxide and water:

2 CH3OH + 3 O2 → 2 CO2 + 4 H2O

One problem with high concentrations of methanol in fuel is that alcohols corrode some metals, particularly aluminium. An acid, albeit weak, methanol attacks the oxide coating that normally protects the aluminium from corrosion:

6 CH3OH + Al2O3 → 2 Al(OCH3)3 + 3 H2O

The resulting methoxide salts are soluble in methanol, resulting in a clean aluminium surface, which is readily oxidized by dissolved oxygen. Also, the methanol can act as an oxidizer:

6 CH3OH + 2 Al → 2 Al(OCH3)3 + 3 H2

This reciprocal process effectively fuels corrosion until either the metal is eaten away or the concentration of CH3OH is negligible. Methanol's corrosivity has been addressed with methanol-compatible materials and fuel additives that serve as corrosion inhibitors. Organic methanol, produced from wood or other organic materials (bioalcohol), has been suggested as a renewable alternative to petroleum-based hydrocarbons. Low levels of methanol can be used in existing vehicles with the addition of cosolvents and corrosion inhibitors. Methanol fuel
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. Usage in the production of biodiesel[edit] Methanol
(and some other alcohols) can be used with a catalyse (such as Sodium hydroxide) to convert plant and animal oil or fat into biodiesel and glycerol in a process called the transesterification reaction.[31][32] Safety in automotive fuels[edit] Pure methanol has been used in open wheel auto racing since the mid-1960s. Unlike petroleum fires, methanol fires can be extinguished with plain water. A methanol-based fire burns invisibly, unlike gasoline, which burns with a visible flame. If a fire occurs on the track, there is no flame or smoke to obstruct the view of fast approaching drivers, but this can also delay visual detection of the fire and the initiation of fire suppression. The decision to permanently switch to methanol in American IndyCar racing was a result of the devastating crash and explosion at the 1964 Indianapolis 500, which killed drivers Eddie Sachs and Dave MacDonald.[33] In 2007 IndyCars switched from methanol to ethanol.[34] Government policy[edit] The European Fuel
Quality Directive allows up to 3% methanol with an equal amount of cosolvent to be blended with gasoline sold in Europe. China
uses more than one billion gallons of methanol per year as a transportation fuel in low level blends for conventional vehicles and high level blends in vehicles designed for methanol fuels. In the US, the Open Fuel
Standard Act of 2011 was introduced in the US Congress to encourage car manufacturers to build cars capable of using methanol, gasoline, or ethanol fuels. The bill is being championed by the Open Fuel
Standard Coalition. Production of synthesis gas[edit] Stoichiometry
for methanol production of syngas requires the ratio of H2 / CO to equal 2. The partial oxidation process yields a ratio of 2, and the steam reforming process yields a ratio of 3. The H2 / CO ratio can be lowered to some extent by the reverse water-gas shift reaction,

CO2 + H2 → CO + H2O,

to provide the appropriate stoichiometry for methanol synthesis. Energy carrier[edit] Methanol
is useful as an energy carrier because it is easier to store than hydrogen and burns cleaner than fossil fuels. Methanol
is readily biodegradable in both aerobic (oxygen present) and anaerobic (oxygen absent) environments. Methanol
will not persist in the environment. 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.[35] Other applications[edit] Methanol
is a traditional denaturant for ethanol, the product being known as "denatured alcohol" or "methylated spirit". This was commonly used during the Prohibition
to discourage consumption of bootlegged liquor, and ended up causing several deaths.[36] Methanol
is used as a solvent and as an antifreeze in pipelines and windshield washer fluid. 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. 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. Methanol
was used as an automobile coolant antifreeze in the early 1900s.[37] Methanol
is used as a destaining agent in polyacrylamide gel electrophoresis. Direct-methanol fuel cells are unique in their low temperature, atmospheric pressure operation, allowing them to be miniaturized to an unprecedented degree.[38][39] 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.[40] 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. 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 is characterized by high selectivity (>99.8%):

CO + 2 H2 → CH3OH

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:[41]

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, which is the same as listed above.

CO + 2 H2 → CH3OH

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:[42]

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

Both Fe- and Cu-dependent enzymes have been characterized.[43] Intense efforts have been undertaken to emulate this reactivity.[44][45] Methanol
is more easily oxidized than is the feedstock methane, so the reactions tend not to be selective. Quality specifications and analysis[edit] Laboratory use[edit] Methanol
is available commercially in various purity grades for fine chemicals:

"Synthesis" quality (corresponding to normal commercial methanol) Certified analytical quality Extremely pure qualities for semiconductor manufacture

Commercial methanol[edit] In addition to laboratory grades, commercial methanol is generally classified according to ASTM purity grades A and AA. 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). When methanol is delivered by ships or tankers used to transport other substances, contamination by the previous cargo must be expected. Comparative ultraviolet spectroscopy has proved a convenient, quick test method for deciding whether a batch can be accepted and loaded. Traces of all chemicals derived from aromatic parent substances, as well as a large number of other compounds, can be detected. Further tests for establishing the quality of methanol include measurements of boiling point range, density, permanganate number, turbidity, color index, and acid number. More comprehensive tests include water determination according to the Karl Fischer method and gas chromatographic determination of byproducts. However, the latter is relatively expensive and time-consuming because several injections using different columns and detectors must be made due to the variety of byproducts present. 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).[46] It later became known as "pyroxylic spirit". In 1834, the French chemists Jean-Baptiste Dumas
Jean-Baptiste Dumas
and Eugene Peligot
Eugene Peligot
determined its elemental composition.[47] They also introduced the word "methylène" to organic chemistry, forming it from Greek methy = "alcoholic liquid" + hȳlē = "woodland, forest", with a Greek language
Greek language
error: xylon = "wood as a material" would have been more suitable. "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.[47] They then called wood alcohol (l'esprit de bois) "bihydrate de méthylène" (bihydrate because they thought the formula was C4H8O4 = (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.[48] The suffix -yl used in organic chemistry to form names of carbon groups, was extracted from the word "methyl". In 1923, the German chemists Alwin Mittasch
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. US patent 1,569,775 was applied for on 4 Sep 1924 and issued on 12 January 1926; 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) was developed by ICI in the late 1960s US 3326956  with the technology now owned by Johnson Matthey, which is a leading licensor of methanol technology. Methanol
is one of the most heavily traded chemical commodities in the world, with an estimated global demand of around 27 to 29 million metric tons. In recent years, production capacity has expanded considerably, with new plants coming on-stream in South America, China and the Middle East, the latter based on access to abundant supplies of methane gas. Even though nameplate production capacity (coal-based) in China
has grown significantly, operating rates are estimated to be as low as 50 to 60%. No new production capacity is scheduled to come on-stream until 2015. The main applications for methanol are the production of formaldehyde (used in construction and wooden boarding), acetic acid (basis for a.o. PET-bottles), MTBE
(fuel component and replacement for the very volatile diethyl ether) and more recently for the formation of methyl esters in the production of bio-diesel. In China, demand is expected to grow exponentially, not only caused by a growing internal market of the traditional applications, but accelerated by new applications, such as direct blending (with gasoline), Methanol-To- Olefins
(e.g. propylene) and DME. Methanol
can also be used to produce gasoline.

Artist’s impression of the disc around the young star TW Hydrae.[49]

The use of methanol as a motor fuel received attention during the oil crises of the 1970s due to its availability, low cost, and environmental benefits. By the mid-1990s, over 20,000 methanol "flexible fuel vehicles" capable of operating on methanol or gasoline were introduced in the U.S. 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 the interest in methanol fuels.[50] In 2006, astronomers using the MERLIN
array of radio telescopes at Jodrell Bank
Jodrell Bank
Observatory discovered a large cloud of methanol in space, 288 billion miles across.[51][52] In 2016, astronomers detected methyl alcohol in a planet-forming disc around the young star TW Hydrae using ALMA radio telescope.[53] See also[edit]

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The Sceptical Chymist
(London, England: J. Cadwell, 1661), pp. 192–195. ^ 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 October 27, 1834 and finished during the meeting of November 3, 1834. See: Procès-verbaux des séances de l'Académie, 10 : 600–601. Available on: Gallica. 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.) ^ 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.  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: 390–400. p. 398: 15. The alcohols and the phenols will be called after the name of the hydrocarbon from which they are derived, terminated with the suffix ol (ex. pentanol, pentenol, etc.). 

^ "Artist's impression of the disc around the young star TW Hydrae". Retrieved 22 June 2016.  ^ Halderman, James D.; Martin, Tony (2009). Hybrid and alternative fuel vehicles. Pearson/Prentice Hall. ISBN 978-0-13-504414-8.  ^ "Upgraded MERLIN
spies cloud of alcohol spanning 288 billion miles" (Press release). Jodrell Bank
Jodrell Bank
Centre for Astrophysics. 19 April 2006. Archived from the original on 20 July 2011.  ^ Amos, Jonathan (5 April 2006). "Merlin sees vast alcohol stream". BBC News.  ^ "First Detection of Methyl Alcohol
in a Planet-forming Disc". Retrieved 22 June 2016. 

Further reading[edit]

Robert Boyle, The Sceptical Chymist
The Sceptical Chymist
(1661) – contains account of distillation of wood alcohol.

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

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Straight-chain primary alcohols (1°)

(C 1) Ethanol
(C 2) 1-Propanol
(C 3) n-Butanol (C 4) 1-Pentanol
(C 5) 1-Hexanol
(C 6) 1-Heptanol
(C 7) 1-Octanol
(C 8) 1-Nonanol
(C 9) 1-Decanol
(C 10) Undecanol
(C 11) Dodecanol
(C 12) Tridecan-1-ol (C 13) 1-Tetradecanol
(C 14) Pentadecan-1-ol (C 15) Cetyl alcohol
Cetyl alcohol
(C 16) Heptadecan-1-ol (C 17) Stearyl alcohol
Stearyl alcohol
(C 18) Nonadecan-1-ol (C 19) Arachidyl alcohol
Arachidyl alcohol
(C 20) Heneicosan-1-ol (C 21) Docosanol
(C 22) Tricosan-1-ol (C 23) 1-Tetracosanol
(C 24) Pentacosan-1-ol (C 25) 1-Hexacosanol
(C 26) 1-Heptacosanol
(C 27) 1-Octacosanol
(C 28) 1-Nonacosanol
(C 29) Triacontanol
(C 30)

Other primary alcohols

(C 4) Isoamyl alcohol
Isoamyl alcohol
(C 5) 2-Methyl-1-butanol
(C 5) Phenethyl alcohol
Phenethyl alcohol
(C 8) Tryptophol
(C 10)

Secondary alcohols (2°)

(C 3) 2-Butanol
(C 4) 2-Pentanol
(C 5) 2-Hexanol
(C 6) 2-Heptanol
(C 7) Cyclohexanol
(C 6) 2-Octanol
(C 8)

Tertiary alcohols (3°)

tert-Butyl alcohol (C 4) tert-Amyl alcohol (C 5) 2-Methyl-2-pentanol
(C 6) 2-Methylhexan-2-ol (C 7) 2-Methylheptan-2-ol (C 8) 3-Methyl-3-pentanol
(C 6) 3-Methyloctan-3-ol (C 9)

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Sugar alcohols


glycol[citation needed]




Erythritol Threitol


Arabitol Ribitol Xylitol


Mannitol Sorbitol Galactitol Iditol



Deoxy sugar alcohols


Cyclic sugar alcohols



Maltitol Lactitol Isomalt Maltotriitol Maltotetraitol Polyglycitol

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Batrachotoxin Bestoxin Birtoxin Bungarotoxin Charybdotoxin Conotoxin Fasciculin Huwentoxin Poneratoxin Saxitoxin Tetrodotoxin Vanillotoxin Spooky toxin (SsTx)


Botulinum toxin Tetanospasmin


Anatoxin-a Anatoxin-a(S) BMAA Saxitoxin


Bicuculline Penitrem A Picrotoxin Strychnine Tutin Rotenone Ginkgotoxin Cicutoxin Oenanthotoxin


Fenpropathrin Tetramethylenedisulfotetramine Bromethalin Crimidine Methamidophos Endosulfan Fipronil

Nerve agents

Cyclosarin EA-3148 Novichok agent Sarin Soman Tabun VE VG VM VR VX GV


Dimethylmercury Toxopyrimidine TBPS IPTBO

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Lumber/ timber

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

Engineered wood

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





Firelog Firewood Pellet fuel Wood


Cardboard Corrugated fiberboard Paper Paperboard Pulp Pulpwood Rayon


Birch-tar Cellulose


Hemicellulose Cellulosic ethanol Dyes Lignin Liquid smoke Lye Methanol Pyroligneous acid Pine tar Pitch Sandalwood oil Tannin Wood


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


Axe ties 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 List of woods Mulch Non-timber forest products Papermaking Wood
drying Wood
preservation Wood
processing Woodworking

portal Trees portal Category Commons WikiProject Forestry

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Molecules detected in outer space



monochloride Aluminium
monofluoride Aluminium
monoxide Argonium Carbon
monophosphide Carbon
monosulfide Carbon
monoxide Carborundum Cyanogen
radical Diatomic carbon Fluoromethylidynium Hydrogen
chloride Hydrogen
fluoride Hydrogen
(molecular) Hydroxyl
radical Iron(II) oxide Magnesium monohydride cation Methylidyne radical Nitric oxide Nitrogen
(molecular) Nitrogen
monohydride Nitrogen
sulfide Oxygen
(molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon mononitride Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfur monohydride Sulfur monoxide Titanium oxide


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 radical N2H+ Nitrous oxide Nitroxyl Ozone Phosphaethyne Potassium cyanide Protonated molecular hydrogen Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide Silicon naphthalocyanine Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water

Four atoms

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

Five atoms

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

Six atoms

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

Seven atoms

Acetaldehyde Acrylonitrile

Vinyl cyanide

Cyanodiacetylene Ethylene
oxide Hexatriynyl radical Methylacetylene Methylamine Methyl isocyanate Vinyl alcohol

Eight atoms

Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Heptatrienyl radical Hexapentaenylidene Methylcyanoacetylene Methyl formate Propenal

Nine atoms

Acetamide Cyanohexatriyne Cyanotriacetylene Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Propionitrile

Ten atoms or more

Acetone Benzene Benzonitrile Buckminsterfullerene
(C60 fullerene, buckyball) C70 fullerene Cyanodecapentayne Cyanopentaacetylene Cyanotetra-acetylene Ethylene
glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propanal n-Propyl cyanide Pyrimidine

Deuterated molecules

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


Anthracene Dihydroxyacetone Ethyl methyl ether Glycine Graphene H2NCO+ Linear C5 Naphthalene
cation Phosphine Pyrene Silylidine


Abiogenesis Astrobiology Astrochemistry Atomic and molecular astrophysics Chemical formula Circumstellar envelope Cosmic dust Cosmic ray Cosmochemistry Diffuse interstellar band Earliest known life forms Extraterrestrial life Extraterrestrial liquid water Forbidden mechanism Helium hydride ion 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 Panspermia Polycyclic aromatic hydrocarbon
Polycyclic aromatic hydrocarbon
(PAH) RNA world hypothesis Spectroscopy Tholin

Book:Chemistry Category:Astrochemistry Category:Molecules Portal:Astrobiology Portal:Astronomy Portal:Chemistry

v t e

GABAA receptor positive modulators


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


(-)-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


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


Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate


6-Methylapigenin Ampelopsin
(dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc-OMe Skullcap constituents (e.g., baicalin) Wogonin


Etomidate Metomidate Propoxate


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


Acecarbromal Apronal
(apronalide) Bromisoval Carbromal Capuride Ectylurea

Neuroactive steroids

Acebrochol Allopregnanolone
(brexanolone) Alfadolone Alfaxalone 3α-Androstanediol Androstenol Androsterone Certain anabolic-androgenic steroids Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone ORG-20599 ORG-21465 P1-185 Pregnanolone
(eltanolone) Progesterone Renanolone SAGE-105 SAGE-217 SAGE-324 SAGE-516 SAGE-689 SAGE-872 Testosterone THDOC


β-Carbolines: Abecarnil Gedocarnil Harmane SL-651,498 ZK-93423

Cyclopyrrolones: Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone

Imidazopyridines: Alpidem DS-1 Necopidem Saripidem Zolpidem

Pyrazolopyrimidines: Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon

Others: Adipiplon CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 CTP-354 ELB-139 GBLD-345 Imepitoin JM-1232 L-838,417 Lirequinil
(Ro41-3696) NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TGSC01AA TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine Y-23684


Fospropofol Propofol Thymol


Glutethimide Methyprylon Piperidione Pyrithyldione


Cartazolate Etazolate ICI-190,622 Tracazolate


Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164


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


3-Hydroxybutanal α-EMTBL AA-29504 Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole DEABL Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine)) DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol) Loreclezole Menthyl isovalerate
Menthyl isovalerate
(validolum) Monastrol Niacin Nicotinamide
(niacinamide) Org 25,435 Phenytoin Propanidid Retigabine
(ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol)

Unsorted benzodiazepine site positive modulators: α-Pinene MRK-409 (MK-0343) TCS-1105 TCS-1205

See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators

Authority control

LCCN: sh85084383 GND: 4128696-0 N


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