Toluene (), also known as toluol (), is a substituted
aromatic hydrocarbon
Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past groupin ...
. It is a colorless,
water
Water (chemical formula ) is an Inorganic compound, inorganic, transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living ...
-insoluble liquid with the smell associated with
paint thinner
A paint thinner is a solvent used to thin oil-based paints. Solvents labeled "paint thinner" are usually mineral spirits having a flash point at about 40 °C (104 °F), the same as some popular brands of charcoal starter.
Common solv ...
s. It is a mono-substituted
benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...
derivative, consisting of a
methyl group
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in ma ...
(CH
3) attached to a
phenyl group. As such, its systematic IUPAC name is methylbenzene. Toluene is predominantly used as an industrial
feedstock and a
solvent
A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
.
As the solvent in some types of
paint thinner
A paint thinner is a solvent used to thin oil-based paints. Solvents labeled "paint thinner" are usually mineral spirits having a flash point at about 40 °C (104 °F), the same as some popular brands of charcoal starter.
Common solv ...
,
permanent marker
A permanent marker or indelible marker is a type of marker pen that is used to create permanent or semi-permanent writing on an object. In general, the ink comprises a main carrier solvent, a glyceride, a pyrrolidone, a resin and a colorant, ma ...
s,
contact cement and certain types of glue, toluene is sometimes used as a recreational
inhalant
Inhalants are a broad range of household and industrial chemicals whose volatile vapors or pressurized gases can be concentrated and breathed in via the nose or mouth to produce intoxication, in a manner not intended by the manufacturer. They ...
and has the potential of causing severe neurological harm.
History
The compound was first isolated in 1837 through a distillation of
pine
A pine is any conifer tree or shrub in the genus ''Pinus'' () of the family Pinaceae. ''Pinus'' is the sole genus in the subfamily Pinoideae. The World Flora Online created by the Royal Botanic Gardens, Kew and Missouri Botanical Garden accepts ...
oil by the
Polish
Polish may refer to:
* Anything from or related to Poland, a country in Europe
* Polish language
* Poles
Poles,, ; singular masculine: ''Polak'', singular feminine: ''Polka'' or Polish people, are a West Slavic nation and ethnic group, w ...
chemist
Filip Walter, who named it ''rétinnaphte''. In 1841, French chemist
Henri Étienne Sainte-Claire Deville
Henri Étienne Sainte-Claire Deville (11 March 18181 July 1881) was a French chemist.
He was born in the island of St Thomas in the Danish West Indies, where his father was French consul. Together with his elder brother Charles he was educate ...
isolated a hydrocarbon from
balsam of Tolu (an aromatic extract from the tropical Colombian tree ''
Myroxylon balsamum
''Myroxylon balsamum'', Santos mahogany, is a species of tree in the family Fabaceae. It is native to tropical forests from Southern Mexico through the Amazon regions of Peru and Brazil at elevations of . Plants are found growing in well d ...
''), which Deville recognized as similar to Walter's ''rétinnaphte'' and to benzene; hence he called the new hydrocarbon ''benzoène''. In 1843,
Jöns Jacob Berzelius recommended the name ''toluin''. In 1850, French chemist
Auguste Cahours isolated from a distillate of wood a hydrocarbon which he recognized as similar to Deville's ''benzoène'' and which Cahours named ''toluène''.
Chemical properties
Toluene reacts as a normal
aromatic hydrocarbon
Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past groupin ...
in
electrophilic aromatic substitution
Electrophilic aromatic substitution is an organic reaction in which an atom that is attached to an aromatic system (usually hydrogen) is replaced by an electrophile. Some of the most important electrophilic aromatic substitutions are aromatic n ...
. Because the
methyl group has greater electron-releasing properties than a
hydrogen
Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic ...
atom in the same position, toluene is more reactive than
benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...
toward electrophiles. It undergoes
sulfonation Aromatic sulfonation is an organic reaction in which a hydrogen atom on an arene is replaced by a sulfonic acid functional group in an electrophilic aromatic substitution. Aryl sulfonic acids are used as detergents, dye, and drugs.
Stoichiometry a ...
to give
''p''-toluenesulfonic acid, and
chlorination Chlorination may refer to:
* Chlorination reaction
In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transform ...
by
Cl2 in the presence of
FeCl3 to give ortho and para
isomers of
chlorotoluene Chlorotoluene is a group of three isomeric chemical compounds. They (''ortho''-chlorotoluene, ''meta''-chlorotoluene, and ''para''-chlorotoluene) consist of a disubstituted benzene ring with one chlorine atom and one methyl group.
Properties
The ...
.
Importantly, the methyl
side chain
In organic chemistry and biochemistry, a side chain is a chemical group that is attached to a core part of the molecule called the "main chain" or backbone. The side chain is a hydrocarbon branching element of a molecule that is attached to a ...
in toluene is susceptible to oxidation. Toluene reacts with
potassium permanganate
Potassium permanganate is an inorganic compound with the chemical formula KMnO4. It is a purplish-black crystalline salt, that dissolves in water as K+ and , an intensely pink to purple solution.
Potassium permanganate is widely used in the c ...
to yield
benzoic acid
Benzoic acid is a white (or colorless) solid organic compound with the formula , whose structure consists of a benzene ring () with a carboxyl () substituent. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, ...
, and with
chromyl chloride
Chromyl chloride is the inorganic compound with the formula CrO2Cl2. It is a reddish brown compound that is a volatile liquid at room temperature, which is unusual for transition metal complexes.
Preparation
Chromyl chloride can be prepared by th ...
to yield
benzaldehyde (
Étard reaction).
The C-H bonds of the methyl group in toluene are
benzylic
In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure . Benzyl features a benzene ring () attached to a methylene group () group.
Nomenclature
In IUPAC nomenclature, the prefix benzyl refers to a subst ...
, which means that they are weaker than C-H bonds in simpler alkanes. Reflecting this weakness, the methyl group in toluene undergoes
halogenation under
free radical
A daughter category of ''Ageing'', this category deals only with the biological aspects of ageing.
Ageing
Ailments of unknown cause
Biogerontology
Biological processes
Causes of death
Cellular processes
Gerontology
Life extension
Metabo ...
conditions. For example, when heated with
''N''-bromosuccinimide (NBS) in the presence of
AIBN, toluene converts to
benzyl bromide
Benzyl bromide is an organic compound with the formula . The molecule consists of a benzene ring substituted with a bromomethyl group. It is a colorless liquid with lachrymatory properties. The compound is a reagent for introducing benzyl groups ...
. The same conversion can be effected with elemental
bromine
Bromine is a chemical element with the symbol Br and atomic number 35. It is the third-lightest element in group 17 of the periodic table ( halogens) and is a volatile red-brown liquid at room temperature that evaporates readily to form a simi ...
in the presence of UV light or even sunlight.
Toluene may also be brominated by treating it with HBr and H
2O
2 in the presence of light.
:C
6H
5CH
3 + Br
2 → C
6H
5CH
2Br + HBr
:C
6H
5CH
2Br + Br
2 → C
6H
5CHBr
2 + HBr
The methyl group in toluene undergoes deprotonation only with very strong bases; its
p''K''a is estimated to be approximately 41. Complete
hydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organ ...
of toluene gives
methylcyclohexane
Methylcyclohexane (cyclohexylmethane) is an organic compound with the molecular formula is CH3C6H11. Classified as saturated hydrocarbon, it is a colourless liquid with a faint odor. Methylcyclohexane is used as a solvent. It is mainly converted ...
. The reaction requires a high pressure of hydrogen and a
catalyst
Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...
.
Miscibility
Toluene is
miscible (soluble in all proportions) with
ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...
,
benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...
,
diethyl ether
Diethyl ether, or simply ether, is an organic compound in the ether class with the formula , sometimes abbreviated as (see Pseudoelement symbols). It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable li ...
,
acetone
Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour.
Acetone is miscib ...
,
chloroform, glacial
acetic acid and
carbon disulfide
Carbon disulfide (also spelled as carbon disulphide) is a neurotoxic, colorless, volatile liquid with the formula and structure . The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical n ...
, but immiscible with water.
Production
Toluene occurs naturally at low levels in crude oil and is a byproduct in the production of
gasoline
Gasoline (; ) or petrol (; ) (see ) is a transparent, petroleum-derived flammable liquid that is used primarily as a fuel in most spark-ignited internal combustion engines (also known as petrol engines). It consists mostly of organi ...
by a
catalytic reformer or
ethylene cracker. It is also a byproduct of the production of
coke from
coal
Coal is a combustible black or brownish-black sedimentary rock, formed as rock strata called coal seams. Coal is mostly carbon with variable amounts of other elements, chiefly hydrogen, sulfur, oxygen, and nitrogen.
Coal is formed when ...
. Final separation and purification is done by any of the
distillation
Distillation, or classical distillation, is the process of separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distillation is the heat ...
or
solvent extraction
A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
processes used for
BTX aromatics (benzene, toluene, and xylene isomers).
[
]
Other preparative routes
Toluene can be prepared by a variety of methods. For example, benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...
reacts with methanol in presence of a solid acid
Solid is one of the four fundamental states of matter (the others being liquid, gas, and plasma). The molecules in a solid are closely packed together and contain the least amount of kinetic energy. A solid is characterized by structural ...
to give toluene:[
:C6H6 + CH3OH -> ^o6H5CH3 + H2O
]
Uses
Precursor to benzene and xylene
Toluene is mainly used as a precursor to benzene via hydrodealkylation:
:C6H5CH3 + H2 → C6H6 + CH4
The second ranked application involves its disproportionation
In chemistry, disproportionation, sometimes called dismutation, is a redox reaction in which one compound of intermediate oxidation state converts to two compounds, one of higher and one of lower oxidation states. More generally, the term can ...
to a mixture of benzene and xylene
In organic chemistry, xylene or xylol (; IUPAC name: dimethylbenzene) are any of three organic compounds with the formula . They are derived from the substitution of two hydrogen atoms with methyl groups in a benzene ring; which hydrogens are s ...
.
Nitration
Nitration of toluene gives mono-, di-, and trinitrotoluene, all of which are widely used. Dinitrotoluene is the precursor to toluene diisocyanate
Toluene diisocyanate (TDI) is an organic compound with the formula CH3C6H3(NCO)2. Two of the six possible isomers are commercially important: 2,4-TDI (CAS: 584-84-9) and 2,6-TDI (CAS: 91-08-7). 2,4-TDI is produced in the pure state, but TDI is oft ...
, which used in the manufacture of polyurethane
Polyurethane (; often abbreviated PUR and PU) refers to a class of polymers composed of organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane is produced from ...
foam. Trinitrotoluene
Trinitrotoluene (), more commonly known as TNT, more specifically 2,4,6-trinitrotoluene, and by its preferred IUPAC name 2-methyl-1,3,5-trinitrobenzene, is a chemical compound with the formula C6H2(NO2)3CH3. TNT is occasionally used as a reage ...
is the explosive typically abbreviated TNT.
Oxidation
Benzoic acid
Benzoic acid is a white (or colorless) solid organic compound with the formula , whose structure consists of a benzene ring () with a carboxyl () substituent. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, ...
and benzaldehyde are produced commercially by partial oxidation Partial oxidation (POX) is a type of chemical reaction. It occurs when a substoichiometric fuel-air mixture is partially combusted in a reformer, creating a hydrogen-rich syngas which can then be put to further use, for example in a fuel cell. A d ...
of toluene with oxygen
Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as ...
. Typical catalysts include cobalt
Cobalt is a chemical element with the symbol Co and atomic number 27. As with nickel, cobalt is found in the Earth's crust only in a chemically combined form, save for small deposits found in alloys of natural meteoric iron. The free element, p ...
or manganese
Manganese is a chemical element with the symbol Mn and atomic number 25. It is a hard, brittle, silvery metal, often found in minerals in combination with iron. Manganese is a transition metal with a multifaceted array of industrial alloy use ...
naphthenates.
:
Solvent
Toluene is a common solvent
A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
, e.g. for paints, paint thinners, silicone sealants, many chemical reactant
A chemical reaction is a process that leads to the chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the positions of electrons in the forming and breaking ...
s, rubber
Rubber, also called India rubber, latex, Amazonian rubber, ''caucho'', or ''caoutchouc'', as initially produced, consists of polymers of the organic compound isoprene, with minor impurities of other organic compounds. Thailand, Malaysia, an ...
, printing
Printing is a process for mass reproducing text and images using a master form or template. The earliest non-paper products involving printing include cylinder seals and objects such as the Cyrus Cylinder and the Cylinders of Nabonidus. The ...
ink, adhesives (glues), lacquers, leather tanners, and disinfectants.[
]
Fuel
Toluene can be used as an octane booster in gasoline
Gasoline (; ) or petrol (; ) (see ) is a transparent, petroleum-derived flammable liquid that is used primarily as a fuel in most spark-ignited internal combustion engines (also known as petrol engines). It consists mostly of organi ...
fuels for internal combustion engine
An internal combustion engine (ICE or IC engine) is a heat engine in which the combustion of a fuel occurs with an oxidizer (usually air) in a combustion chamber that is an integral part of the working fluid flow circuit. In an internal c ...
s as well as jet fuel. Toluene at 86% by volume fuelled all the turbocharged engines in Formula One
Formula One (also known as Formula 1 or F1) is the highest class of international racing for open-wheel single-seater formula racing cars sanctioned by the Fédération Internationale de l'Automobile (FIA). The World Drivers' Championship, ...
during the 1980s, first pioneered by the Honda
is a Japanese public multinational conglomerate manufacturer of automobiles, motorcycles, and power equipment, headquartered in Minato, Tokyo, Japan.
Honda has been the world's largest motorcycle manufacturer since 1959, reaching a producti ...
team. The remaining 14% was a "filler" of ''n''-heptane
Heptane or ''n''-heptane is the straight-chain alkane with the chemical formula H3C(CH2)5CH3 or C7H16. When used as a test fuel component in anti-knock test engines, a 100% heptane fuel is the zero point of the octane rating scale (the 100 poin ...
, to reduce the octane rating to meet Formula One fuel restrictions. Toluene at 100% can be used as a fuel for both two-stroke
A two-stroke (or two-stroke cycle) engine is a type of internal combustion engine that completes a power cycle with two strokes (up and down movements) of the piston during one power cycle, this power cycle being completed in one revolution of ...
and four-stroke engine
A four-stroke (also four-cycle) engine is an internal combustion (IC) engine in which the piston completes four separate strokes while turning the crankshaft. A stroke refers to the full travel of the piston along the cylinder, in either directi ...
s; however, due to the density
Density (volumetric mass density or specific mass) is the substance's mass per unit of volume. The symbol most often used for density is ''ρ'' (the lower case Greek letter rho), although the Latin letter ''D'' can also be used. Mathematical ...
of the fuel and other factors, the fuel does not vaporize easily unless preheated to . Honda solved this problem in their Formula One cars by routing the fuel lines through a heat exchanger
A heat exchanger is a system used to transfer heat between a source and a working fluid. Heat exchangers are used in both cooling and heating processes. The fluids may be separated by a solid wall to prevent mixing or they may be in direct conta ...
, drawing energy from the water in the cooling system to heat the fuel.
In Australia in 2003, toluene was found to have been illegally combined with petrol in fuel outlets for sale as standard vehicular fuel. Toluene incurs no fuel excise tax, while other fuels are taxed at more than 40%, providing a greater profit margin
Profit margin is a measure of profitability. It is calculated by finding the profit as a percentage of the revenue.
\text = =
There are 3 types of profit margins: gross profit margin, operating profit margin and net profit margin.
* Gross Pro ...
for fuel suppliers. The extent of toluene substitution has not been determined.
Niche applications
In the laboratory, toluene is used as a solvent for carbon nanomaterials, including nanotubes and fullerenes, and it can also be used as a fullerene
A fullerene is an allotrope of carbon whose molecule consists of carbon atoms connected by single and double bonds so as to form a closed or partially closed mesh, with fused rings of five to seven atoms. The molecule may be a hollow sphere, ...
indicator. The color of the toluene solution of C60 is bright purple. Toluene is used as a cement for fine polystyrene kits Kits may refer to:
*Kitsilano, a neighbourhood of the city of Vancouver, British Columbia, Canada
*Kits, an American taffy candy made by Gilliam Candy Company
* KITS, a San Francisco, California radio station
* Kottayam Institute of Technology & Sc ...
(by dissolving and then fusing surfaces) as it can be applied very precisely by brush and contains none of the bulk of an adhesive. Toluene can be used to break open red blood cell
Red blood cells (RBCs), also referred to as red cells, red blood corpuscles (in humans or other animals not having nucleus in red blood cells), haematids, erythroid cells or erythrocytes (from Greek ''erythros'' for "red" and ''kytos'' for "holl ...
s in order to extract hemoglobin
Hemoglobin (haemoglobin BrE) (from the Greek word αἷμα, ''haîma'' 'blood' + Latin ''globus'' 'ball, sphere' + ''-in'') (), abbreviated Hb or Hgb, is the iron-containing oxygen-transport metalloprotein present in red blood cells (erythrocyt ...
in biochemistry experiments. Toluene has also been used as a coolant for its good heat transfer capabilities in sodium cold traps used in nuclear reactor system loops. Toluene had also been used in the process of removing the cocaine from coca leaves in the production of Coca-Cola syrup.
Toxicology and metabolism
The environmental and toxicological effects of toluene have been extensively studied. Inhalation of toluene in low to moderate levels can cause tiredness, confusion, weakness, drunken-type actions, memory loss, nausea, loss of appetite, hearing loss
Hearing loss is a partial or total inability to hear. Hearing loss may be present at birth or acquired at any time afterwards. Hearing loss may occur in one or both ears. In children, hearing problems can affect the ability to acquire spoken ...
, and colour vision loss. Some of these symptoms usually disappear when exposure is stopped. Inhaling high levels of toluene in a short time may cause light-headedness, nausea, or sleepiness, unconsciousness, and even death
Death is the irreversible cessation of all biological functions that sustain an organism. For organisms with a brain, death can also be defined as the irreversible cessation of functioning of the whole brain, including brainstem, and brain ...
. Toluene is, however, much less toxic than benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...
, and as a consequence, largely replaced it as an aromatic solvent in chemical preparation. The US Environmental Protection Agency
The Environmental Protection Agency (EPA) is an independent executive agency of the United States federal government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it be ...
(EPA) states that the carcinogen
A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive subs ...
ic potential of toluene cannot be evaluated due to insufficient information. In 2013, worldwide sales of toluene amounted to about 24.5 billion US-dollars.
Similar to many other solvents such as 1,1,1-trichloroethane
The organic compound 1,1,1-trichloroethane, also known as methyl chloroform, is a chloroalkane. This colorless, sweet-smelling liquid was once produced industrially in large quantities for use as a solvent. It is regulated by the Montreal Prot ...
and some alkyl
In organic chemistry, an alkyl group is an alkane missing one hydrogen.
The term ''alkyl'' is intentionally unspecific to include many possible substitutions.
An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloa ...
benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...
s, toluene has been shown to act as a non-competitive NMDA receptor antagonist
NMDA receptor antagonists are a class of drugs that work to antagonize, or inhibit the action of, the ''N''-Methyl-D-aspartate receptor ( NMDAR). They are commonly used as anesthetics for animals and humans; the state of anesthesia they induce ...
and GABAA receptor positive allosteric modulator
In pharmacology and biochemistry, allosteric modulators are a group of substances that bind to a receptor to change that receptor's response to stimulus. Some of them, like benzodiazepines, are drugs. The site that an allosteric modulator binds to ...
. Additionally, toluene has been shown to display antidepressant-like effects in rodents in the forced swim test
The behavioural despair test (or Porsolt forced swimming test) is a test, centered on a rodent's response to the threat of drowning, whose result has been interpreted as measuring susceptibility to negative mood. It is commonly used to measure the ...
(FST) and the tail suspension test
The tail suspension test (TST) is an experimental method used in scientific research to measure stress in rodents. It is based on the observation that if a mouse is subjected to short term inescapable stress then the mouse will become immobile ...
(TST), likely due to its NMDA antagonist properties.
Toluene is sometimes used as a recreational inhalant
Inhalants are a broad range of household and industrial chemicals whose volatile vapors or pressurized gases can be concentrated and breathed in via the nose or mouth to produce intoxication, in a manner not intended by the manufacturer. They ...
("glue sniffing"), likely on account of its euphoric
Euphoria ( ) is the experience (or affect) of pleasure or excitement and intense feelings of well-being and happiness. Certain natural rewards and social activities, such as aerobic exercise, laughter, listening to or making music and da ...
and dissociative
Dissociatives, colloquially dissos, are a subclass of hallucinogens which distort perception of sight and sound and produce feelings of detachment – dissociation – from the environment and/or self. Although many kinds of drugs are capable of ...
effects.
Toluene inhibits excitatory ion channels such as the NMDA receptor, nicotinic acetylcholine receptor
Nicotinic acetylcholine receptors, or nAChRs, are receptor polypeptides that respond to the neurotransmitter acetylcholine. Nicotinic receptors also respond to drugs such as the agonist nicotine. They are found in the central and peripheral ner ...
, and the serotonin 5-HT3 receptor. It also potentiates the function of inhibitory ion channels, such as the GABAA and glycine receptors
The glycine receptor (abbreviated as GlyR or GLR) is the receptor of the amino acid neurotransmitter glycine. GlyR is an ionotropic receptor that produces its effects through chloride current. It is one of the most widely distributed inhibitory ...
. In addition, toluene disrupts voltage-gated calcium channels and ATP-gated ion channels.
Recreational use
Toluene is used as an intoxicative inhalant
Inhalants are a broad range of household and industrial chemicals whose volatile vapors or pressurized gases can be concentrated and breathed in via the nose or mouth to produce intoxication, in a manner not intended by the manufacturer. They ...
in a manner unintended by manufacturers. People inhale toluene-containing products (e.g., paint thinner
A paint thinner is a solvent used to thin oil-based paints. Solvents labeled "paint thinner" are usually mineral spirits having a flash point at about 40 °C (104 °F), the same as some popular brands of charcoal starter.
Common solv ...
, contact cement, model glue, etc.) for its intoxicating effect. The possession and use of toluene and products containing it are regulated in many jurisdictions, for the supposed reason of preventing minors from obtaining these products for recreational drug purposes. As of 2007, 24 U.S. states had laws penalizing use, possession with intent to use, and/or distribution of such inhalants. In 2005 the European Union
The European Union (EU) is a supranational political and economic union of member states that are located primarily in Europe. The union has a total area of and an estimated total population of about 447million. The EU has often been de ...
banned the general sale of products consisting of greater than 0.5% toluene.
Bioremediation
Several types of fungi including '' Cladophialophora'', ''Exophiala
''Exophiala'' is a genus of Teleomorph, anamorph and holomorph, anamorphic fungus, fungi in the family Herpotrichiellaceae. The widespread genus contains 28 species. The genus was formally described by J. W. Carmichael in 1966.
''Exophiala'' has ...
'', ''Leptodontidium
''Leptodontidium'' is a genus of fungi
A fungus ( : fungi or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. These organisms a ...
'' ( syn. ''Leptodontium''), '' Pseudeurotium zonatum'', and '' Cladosporium sphaerospermum'', and certain species of bacteria can degrade toluene using it as a source of carbon and energy.
References
External links
ATSDR – Case Studies in Environmental Medicine: Toluene Toxicity
U.S. Department of Health and Human Services (public domain)
*American Industrial Hygiene Association The American Industrial Hygiene Association (AIHA) is a 501(c)6 non-profit organization, whose mission is "Creating knowledge to protect worker health." The American Industrial Hygiene Association works to provide information and resources to Ind ...
The Ear Poisons
The Synergist, November 2018.
Toluene
CDC – NIOSH Workplace Safety and Health Topic (DHHS)
* OSHA-NIOSH 2018. Preventing Hearing Loss Caused by Chemical (Ototoxicity) and Noise Exposure Safety and Health Information Bulletin (SHIB), Occupational Safety and Health Administration and the National Institute for Occupational Safety and Health. SHIB 03-08-2018. DHHS (NIOSH) Publication No. 2018-124.
{{Authority control
Hazardous air pollutants
Hydrocarbon solvents
Antiknock agents
Alkylbenzenes
Commodity chemicals
Petrochemicals
GABAA receptor positive allosteric modulators
Glycine receptor agonists
Euphoriants
Inhalants
Aromatic solvents
Phenyl compounds
Occupational safety and health
NMDA receptor antagonists