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DNo Author, xx [No Author, xx-xx-xxxx, No Publication, "Ethanol", https://en.wikipedia.org/wiki/Ethanol, Accessed 11-9-2015, GJ]

Ethanol
From Wikipedia, the free encyclopedia

"Drinking alcohol" redirects here. For information related to the

consumption of alcohol, see Alcoholic beverage.
For other uses, see Ethanol (disambiguation).

Ethanol

Names
Systematic IUPAC name
ethanol[1]
Other names
Absolute alcohol, alcohol, cologne spirit, drinking alcohol, ethane
monoxide, ethylic alcohol, EtOH, ethyl alcohol, ethyl hydrate, ethyl
hydroxide, ethylol, grain alcohol, hydroxyethane, methylcarbinol
Identifiers
CAS Registry Number

64-17-5

ChemSpider

682

InChI[show]
IUPHAR/BPS

2299

Jmol-3D images

Image

PubChem

702

SMILES[show]
Properties
Chemical formula

C2H6O

Molar mass

46.07 g/mol

Appearance

Colorless liquid

Density

0.789 g/cm3 (at 20C)

Melting point

114 C (173 F; 159 K)

Boiling point

78.37 C (173.07 F; 351.52 K)

log P

-0.18

Vapor pressure

5.95 kPa (at 20 C)

Acidity (pKa)

15.9 (H2O), 29.8 (DMSO)[2][3]

Basicity (pKb)

-1.9

Refractive index(nD)

1.361

Viscosity

0.0012 Pa s (at 20 C), 0.001074 Pa s (at

25 C)[4]

Dipole moment

1.69 D[5]
Pharmacology

ATC code

D08AX08
V03AB16, V03AZ01

DrugBank

DB00898

Legal status

AU:

Unscheduled

CA: Unscheduled
NZ: Unscheduled
UK: Unscheduled
US: Unscheduled

[10]

UN: Unscheduled
EU: Unscheduled

Pregnancy

US: C

category
Dependence liability

Moderate[13]

Addiction liability

Moderate[12]

Routes of

Common: oral

administration

(Risk not ruled out) [11]

Uncommon: suppository, inhalation,

ocular, insufflation,[6] injection[7]

Pharmacokinetics:
Bioavailability

Variable[8]

Metabolism

Hepatic enzyme alcohol dehydrogenase

Metabolites

Acetaldehyde, acetic acid,acetylCoA, carbon dioxide,water

Biological half-life

None, constant rate elimination[9]

Excretion

Urine, breath, perspiration, tears, milk,

saliva, bile[9]
Related compounds

Related compounds

Ethane
Methanol
Supplementary data page

Structure and
properties

Refractive index (n),

Dielectric constant (r), etc.

Thermodynamic
data
Spectral data

Phase behaviour
solidliquidgas
UV, IR, NMR, MS

Except where otherwise noted, data are given for materials in

their standard state (at 25 C [77 F], 100 kPa).
verify (what is:

/ ?)

Infobox references

Ethanol /nl/, also commonly called ethyl alcohol, drinking

alcohol, or simply alcohol is the principal type of alcohol found
in alcoholic beverages, produced by
the fermentation of sugars byyeasts. It is a neurotoxic[14][15] psychoactive
drug and one of the oldest recreational drugs used by humans. It can
cause alcohol intoxication when consumed in sufficient quantity.
Ethanol is a volatile, flammable, colorless liquid with a slight chemical
odor. It is used as an antiseptic, a solvent, a fuel, and, due to its low
freezing point, the active fluid in post-mercurythermometers. Its
structural formula, CH
3CH
2OH, is often abbreviated as C
2H
5OH, C
2H
6O or EtOH.
Contents
[hide]

1Etymology

2Chemical formula

3Uses
o 3.1Medical
o 3.2Recreational
o 3.3Fuel
o 3.4Feedstock
o 3.5Solvent

4Adverse effects
o 4.1Loss of balance
o 4.2Gastrointestinal diseases
o 4.3Short-term toxic allergy-like responses
o 4.4Long-term

5Overdose
o 5.1Addiction

5.2Dependence and withdrawal

6Interactions
o 6.1Alcohol and metronidazole

7Pharmacology
o 7.1Pharmacodynamics
o 7.2Pharmacokinetics

8Physical and chemical properties

o 8.1Physical properties
o 8.2Solvent properties
o 8.3Flammability

9Natural occurrence

10Production
o 10.1Ethylene hydration
o 10.2Fermentation
o 10.3Testing

11Purification
o 11.1Distillation
o 11.2Molecular sieves and desiccants
o 11.3Membranes and reverse osmosis
o 11.4Other techniques
o 11.5Grades of ethanol

12Reactions
o 12.1Ester formation
o 12.2Dehydration
o 12.3Combustion
o 12.4Acid-base chemistry
o 12.5Halogenation
o 12.6Oxidation

13History

14Society and culture

15See also

16References

17Further reading

18External links

Etymology[edit]
Ethanol is the systematic name defined by the International Union of
Pure and Applied Chemistry (IUPAC) for a molecule with two carbon
atoms (prefix "eth-"), having a single bond between them (suffix "-ane"),
and an attached functional group-OH group (suffix "-ol").[1]
The prefix ethyl was coined in 1834 by the German chemist Justus
Liebig.[16] Ethyl is a contraction of the French word ether (any substance

that evaporated or sublimated readily at room temperature) and the

Greek word (hyle, substance).[17]
The name ethanol was coined as a result of a resolution that was
adopted at the International Conference on Chemical Nomenclature that
was held in April 1892 in Geneva, Switzerland.[18]
The term "alcohol" now refers to a wider class of substances in
chemistry nomenclature, but in common parlance it remains the name
of ethanol. Ultimately a medieval loan from Arabic al-kuh l,[19]use
of alcohol in this sense is modern, introduced in the mid 18th century.
Before that time, Middle Latin alcohol referred to "powdered ore of
antimony; powdered cosmetic", by the later 17th century "any
sublimated substance; distilled spirit" use for "the spirit of wine"
(shortened from a full expression alcohol of wine) recorded 1753. The
systematic use in chemistry dates to 1850.

Chemical formula[edit]
Ethanol is a 2-carbon alcohol. Its molecular formula is CH3CH2OH. An
alternative notation is CH3CH2OH, which indicates that the carbon of
a methyl group (CH3) is attached to the carbon of amethylene group (
CH2), which is attached to the oxygen of a hydroxyl group (OH). It is a
constitutional isomer of dimethyl ether. Ethanol is sometimes
abbreviated as EtOH, using the common organic chemistry notation of
representing the ethyl group (C2H5-) with Et.

Uses[edit]
Medical[edit]
Antiseptic[edit]
Ethanol is used in medical wipes and in most common
antibacterial hand sanitizer gels at a concentration of about 62% v/v as
an antiseptic. Ethanol kills organisms by denaturing their proteins and
dissolving their lipids and is effective against most bacteria and fungi,
and many viruses, but is ineffective against bacterial spores.[20]
Antitussive[edit]
Ethanol is also widely used, clinically and over the counter, as
an antitussive agent.[21]
Antidote[edit]
Ethanol may be administered as an antidote to methanol poisoning.[22]
Medicinal solvent[edit]
Ethanol, often in surprisingly high concentrations, is used to dissolve
many water-insoluble medications and related compounds. Proprietary
liquid preparations of cough and cold remedies, analgesics, and mouth
washes may be dissolved in 1 to 25% concentrations of ethanol and
may need to be avoided in individuals with adverse reactions to ethanol
such as alcohol-induced respiratory reactions.[23]

Recreational[edit]

Ethanol is a central nervous system depressant and has significant

psychoactive effects in sublethal doses. Based on its abilities to
alter human consciousness, ethanol is considered a psychoactive drug.
[24]

The amount of ethanol in the body is typically quantified by blood

alcohol content (BAC), which is here taken as weight of ethanol per unit
volume of blood. Small doses of ethanol, in general, produce euphoria
and relaxation; people experiencing these symptoms tend to become
talkative and less inhibited, and may exhibit poor judgment. At higher
dosages (BAC > 1 g/L), ethanol acts as a central nervous
system depressant, producing at progressively higher dosages,
impaired sensory and motor function, slowed cognition, stupefaction,
unconsciousness, and possible death. Ethanol is commonly consumed
as a recreational drug, especially while socializing, due to its
psychoactive effects.

Fuel[edit]
Engine fuel[edit]
Energy content of some fuels compared with ethanol:[25]

Fuel type

MJ/L

Dry wood (20%

moisture)

Research
octane
number

MJ/kg

~19.5

Methanol

17.9

19.9

108.7[26]

Ethanol

21.2[27]

26.8[27]

108.6[26]

E85
(85% ethanol, 15%
gasoline)

25.2

33.2

105

Liquefied natural gas

25.3

~55

Autogas (LPG)
(60% propane +
40% butane)

26.8

50.

Aviation gasoline
(high-octane gasoline,
not jet fuel)

33.5

46.8

100/130 (lean/rich)

Gasohol
(90% gasoline + 10%
ethanol)

33.7

47.1

93/94

Regular gasoline/petrol

34.8

44.4[28]

min. 91

Premium gasoline/petrol

max. 104

Diesel

38.6

45.4

Charcoal, extruded

50

23

25

Main article: Ethanol fuel

The largest single use of ethanol is as an engine fuel and fuel
additive. Brazil in particular relies heavily upon the use of ethanol as an
engine fuel, due in part to its role as the globe's leading producer of
ethanol.[29] Gasoline sold in Brazil contains at least
25% anhydrous ethanol. Hydrous ethanol (about 95% ethanol and 5%
water) can be used as fuel in more than 90% of new gasoline-engined
cars sold in the country. Brazilian ethanol is produced from sugar
cane and noted for highcarbon sequestration.[30] The US uses Gasohol
(max 10% ethanol) and E85 (85% ethanol) ethanol/gasoline mixtures.

USP grade ethanol for laboratory use.

Ethanol may also be utilized as a rocket fuel, and is currently

in lightweight rocket-powered racing aircraft.[31]
Australian law limits the use of pure ethanol sourced from sugarcane
waste to up to 10% in automobiles. It has been recommended that older
cars (and vintage cars designed to use a slower burning fuel) have their
valves upgraded or replaced.[32]
According to an industry advocacy group, ethanol as a fuel reduces
harmful tailpipe emissions of carbon monoxide, particulate
matter, oxides of nitrogen, and other ozone-forming pollutants.
[33]
Argonne National Laboratory analyzed the greenhouse gas emissions
of many different engine and fuel combinations. Comparing ethanol
blends with gasoline alone, they showed reductions of 8% with
the biodiesel/petrodiesel blend known as B20, 17% with the
conventional E85 ethanol blend, and that using cellulosic ethanol lowers
emissions 64%.[34]
Ethanol combustion in an internal combustion engine yields many of the
products of incomplete combustion produced by gasoline and
significantly larger amounts of formaldehyde and related species such
as acetaldehyde.[35] This leads to a significantly larger photochemical
reactivity that generates much more ground level ozone.[36] These data
have been assembled into The Clean Fuels Report comparison of fuel
emissions[37] and show that ethanol exhaust generates 2.14 times as
much ozone as does gasoline exhaust.[citation needed] When this is added into
the custom Localised Pollution Index (LPI) of The Clean Fuels Report
the local pollution (pollution that contributes to smog) is 1.7 on a scale
where gasoline is 1.0 and higher numbers signify greater pollution. [citation
needed]
The California Air Resources Board formalized this issue in 2008 by
recognizing control standards for formaldehydes as an emissions
control group, much like the conventional NOx and Reactive Organic
Gases (ROGs).[38]

World production of ethanol in 2006 was 51 gigalitres (1.31010 US gal),

with 69% of the world supply coming from Brazil and the United States.
[39]
More than 20% of Brazilian cars are able to use 100% ethanol as
fuel, which includes ethanol-only engines and flex-fuel engines.[40] Flexfuel engines in Brazil are able to work with all ethanol, all gasoline or
any mixture of both. In the US flex-fuel vehicles can run on 0% to 85%
ethanol (15% gasoline) since higher ethanol blends are not yet allowed
or efficient. Brazil supports this population of ethanol-burning
automobiles with large national infrastructure that produces ethanol
from domestically grownsugar cane. Sugar cane not only has a greater
concentration of sucrose than corn (by about 30%), but is also much
easier to extract. The bagasse generated by the process is not wasted,
but is used in power plants to produce electricity.[citation needed]
The United States fuel ethanol industry is based largely on corn.
According to the Renewable Fuels Association, as of 30 October 2007,
131 grain ethanol bio-refineries in the United States have the capacity to
produce 7.0 billion US gallons (26,000,000 m3) of ethanol per year. An
additional 72 construction projects underway (in the U.S.) can add
6.4 billion US gallons (24,000,000 m3) of new capacity in the next 18
months. Over time, it is believed that a material portion of the 150billion-US-gallon (570,000,000 m3) per year market for gasoline will
begin to be replaced with fuel ethanol.[41]
Sweet sorghum is a potential source of ethanol, which is suitable for
growing in dryland conditions. It is being investigated by
the International Crops Research Institute for the Semi-Arid
Tropics (ICRISAT) for its potential to provide fuel, along with food and
animal feed, in arid parts of Asia and Africa.[42] The water requirement
of sweet sorghum is one-third that of sugarcane on a comparable time
scale. Also, sweet sorghum requires about 22% less water than corn
also known as maize. The worlds first sweet sorghum-based ethanol
production distillery began commercial ethanol production in 2007 in
Andhra Pradesh, India.[43]
Ethanol's high miscibility with water means that it cannot be shipped
through modern pipelines like liquid hydrocarbons.[44] Mechanics have
seen increased cases of damage to small engines, in particular,
thecarburetor, attributable to the increased water retention by ethanol in
fuel.[45]

Ethanol pump station in So Paulo, Brazil

A Ford Taurus fueled by ethanol inNew York City

USPS truck running on E85 inMinnesota

Rocket Fuel[edit]
Ethanol was commonly used as fuel in early bipropellant rocket (liquid
propelled) vehicles, in conjunction with an oxidizer such as liquid
oxygen. The German V-2 rocket of World War II, credited with beginning
the space age, used ethanol, mixed with 25% of water to reduce the
combustion chamber temperature.[46][47] The V-2's design team helped
develop U.S. rockets following World War II, including the ethanolfueled Redstone rocket which launched the first U.S. satellite.[48]Alcohols
fell into general disuse as more efficient rocket fuels were developed.[47]
Fuel Cells[edit]
Commercial fuel cells operate on reformed natural
gas, hydrogen or methanol. Ethanol is an attractive alternative due to its
wide availability, low cost, high purity and low toxicity. There are a wide
range of fuel cell concepts that have been trialled including directethanol fuel cells, auto-thermal reforming systems and thermally
integrated systems. The majority of work is being conducted at a
research level although there are a number of organizations at the
beginning of commercialization of ethanol fuel cells.[49]
Household heating[edit]

An example of a bio-ethanol fire in the form of a traditional fireplace, using

fire-proof ceramic simulated wood logs for effect.

Ethanol fuels flue-less, real flame fireplaces. Ethanol is kept in a burner

containing a wick such as glass wool, a safety shield to reduce the
chances of accidents and an extinguisher such as a plate or shutter to
cut off oxygen.
It provides almost the same visual benefits of a real flame log or coal
fire without the need to vent the fumes via a flue as ethanol produces
very little hazardous carbon monoxide, and little or no noticeable scent.
It does emit carbon dioxide and requires oxygen. Therefore, external
ventilation of the room containing the fire is needed to ensure safe
operation.
An additional benefit is that, unlike a flue based fireplace, 100% of the
heat energy produced enters the room. This serves to offset some of the
heat loss from an external air vent, as well as offset the relatively high
cost of the fuel compared to other forms of heating.

Feedstock[edit]
Further information: Reactions
Ethanol is an important industrial ingredient. It has widespread use as a
precursor for other organic compounds such as ethyl halides,
ethyl esters, diethyl ether, acetic acid, and ethyl amines.

Solvent[edit]
Ethanol is miscible with water and is a good general purpose solvent. It
is found in paints, tinctures, markers, and personal care products such
as mouthwashes, perfumes and deodorants.
However, polysaccharides precipitate from aqueous solution in the
presence of alcohol, and ethanol precipitation is used for this reason in
the purification of DNA and RNA.

Adverse effects[edit]
Main articles: Alcohol and health and Short-term effects of alcohol

Loss of balance[edit]
When alcohol reaches the brain, it has the ability to delay signals that
are sent between nerve cells that control balance, thinking and
movement.[50]

Gastrointestinal diseases[edit]

Diagram of mucosal layer

Alcohol stimulates gastric juice production, even when food is not

present. In other words, when a person drinks alcohol, the alcohol will
stimulate stomach's acidic secretions that are intended to digest protein
molecules. Consequently, the acidity has potential to harm the inner
lining of the stomach. Normally, the stomach lining is protected by a
mucus layer that prevents any acids from reaching the stomach cells.
However, in patients who have a peptic ulcer disease (PUD), this mucus
layer is broken down. PUD is commonly associated with a bacteria H.
pylori. H. pylori secretes a toxin that weakens the mucosal wall. As a
result, acid and protein enzymes penetrate the weakened barrier.
Because alcohol stimulates a person's stomach to secrete acid, a
person with PUD should avoid drinking alcohol on an empty stomach.
Drinking alcohol would cause more acid release to damage the
weakened stomach wall.[51] Complications of this disease could include a
burning pain in the abdomen, bloating and in severe cases, the
presence of dark black stools indicate internal bleeding. [52] A person who
drinks alcohol regularly is strongly advised to reduce their intake to
prevent PUD aggravation.[52]

Short-term toxic allergy-like responses[edit]

Main articles: Alcohol-induced respiratory reactions and Alcohol flush
reaction
Ethanol-containing beverages can cause urticarial skin eruptions,
systemic dermatitis, alcohol flush reactions, exacerbations
of rhinitis and, more seriously and commonly, bronchoconstriction in
patients with a history of asthma. These reactions occur within 160
minutes of ethanol ingestion and are due to: 1) genetic abnormalities in
the metabolism of ethanol which cause the ethanol
metabolite, acetaldehyde, to accumulate in tissues and trigger the
release of histamine, the evoker of these
symptoms; 2) true allergy reactions to allergens occurring naturally in, or
contaminating, alcoholic beverages, particularly wines and beers,
and 3) unknown causes.[23]

Long-term[edit]
Main article: Long-term effects of alcohol
Birth defects[edit]
See also: fetal alcohol syndrome and fetal alcohol spectrum disorder

Ethanol is classified as a teratogen.

Cancer[edit]
IARC list ethanol in alcoholic beverages as Group 1 carcinogens and
arguments "There is sufficient evidence for
the carcinogenicity of acetaldehyde (the major metabolite of ethanol) in
experimental animals.".[53]
Other effects[edit]
Frequent drinking of alcoholic beverages has been shown to be a major
contributing factor in cases of elevated blood levels of triglycerides.[54]

Overdose[edit]
See also: Alcohol consumption and health
BAC
(% v/v)

BAC (g/L)

Symptoms[55]

0.05%

Euphoria,
talkativeness,
relaxation

0.1 %

Central nervous
system depression,
nausea, possible
vomiting, impaired
motor and sensory
function, impaired
cognition

>1.4

>0.14%

Decreased blood
flow to brain

0.3%

Stupefaction,
possible
unconsciousness

0.4%

Possible death

>5.5

>0.55%

Death

0.5

Death from ethanol consumption is possible when blood alcohol levels

reach 0.4%. A blood level of 0.5% or more is commonly fatal. Levels of
even less than 0.1% can causeintoxication, with unconsciousness often
occurring at 0.30.4%.[56]
Prolonged heavy consumption of alcohol can cause significant
permanent damage to the brain and other organs.

Addiction[edit]
See also: Alcoholism
The reinforcing effects of alcohol consumption are mediated
by acetaldehyde generated by catalase and other oxidizing enzymes
such as cytochrome P-4502E1 in the brain.[57]Although acetaldehyde has
been associated with some of the adverse and toxic effects of ethanol, it
appears to play a central role in the activation of the mesolimbic
dopamine system.[58]
Ethanol's rewarding and reinforcing (i.e., addictive) properties are
mediated through its effects on dopamine neurons in the mesolimbic
reward pathway, which connects the ventral tegmental area to
the nucleus accumbens (NAcc).[59][60] One of ethanol's primary effects is
the allosteric inhibition of NMDA receptors and facilitation
of GABAA receptors (e.g., enhanced GABAA receptormediated chloride flux through allosteric regulation of the receptor).[61] At
high doses, ethanol inhibits most ligand gated ion channels and voltage
gated ion channels in neurons as well.[61]
With acute alcohol consumption, dopamine is released in
the synapses of the mesolimbic pathway, in turn heightening activation
of postsynaptic D1 receptors.[59][60] The activation of these receptors
triggers postsynaptic internal signaling events through protein kinase
A which ultimately phosphorylate cAMP response element binding
protein (CREB), inducing CREB-mediated changes in gene expression.
[59][60]

With chronic alcohol intake, consumption of ethanol similarly induces

CREB phosphorylation through the D1 receptor pathway, but it also
alters NMDA receptor function through phosphorylation mechanisms;[59]
[60]
an adaptive downregulationof the D1 receptor pathway and CREB
function occurs as well.[59][60] Chronic consumption is also associated with
an effect on CREB phosphorylation and function via postsynaptic NMDA
receptor signaling cascades through a MAPK/ERK pathway and CAMKmediated pathway.[60] These modifications to CREB function in the
mesolimbic pathway induce expression (i.e., increase gene expression)
of FosB in the NAcc,[60] where FosB is the "master control protein"
that, when overexpressed in the NAcc, is necessary and sufficient for
the development and maintenance of an addictive state (i.e., its
overexpression in the nucleus accumbens produces and then directly
modulates compulsive alcohol consumption).[60][62][63][64]

Dependence and withdrawal[edit]

See also: Alcoholism
Discontinuing consumption of alcohol after several years of heavy
drinking can also be fatal. Alcohol withdrawal can cause anxiety,
autonomic dysfunction, seizures, and hallucinations. Delirium tremens is

a condition that requires people with a long history of heavy drinking to

undertake an alcohol detoxification regimen.

Interactions[edit]
Ethanol can intensify the sedation caused by other central nervous
system depressant drugs such
as barbiturates, benzodiazepines, opioids, non-benzodiazepines (such
as Zolpidem and Zopiclone), antipsychotics, sedative antihistamines,
and antidepressants.[56] It interacts with cocaine in vivo to
produce cocaethylene, another psychoactive substance.[65] Ethanol
enhances the bioavailability of methylphenidate (elevated plasma dMPH).[66] In combination with cannabis, ethanol increases plasma THC
levels, which suggests that ethanol may increase the absorption of
THC.[67]

Alcohol and metronidazole[edit]

One of the most important drug/food interactions that should be noted is
between alcohol and metronidazole.
Metronidazole is an antibacterial agent that kills bacteria by damaging
cellular DNA and hence cellular function.[68] Metronidazole is usually
given to people who have diarrhea caused by Clostridium
difficile bacteria. C. difficile is one of the most common microorganisms
that cause diarrhea and can lead to complications such as colon
inflammation and even more severely, death.
Patients who are taking metronidazole are strongly advised to avoid
alcohol, even after 1 hour after the last dose. The reason is that alcohol
and metronidazole can lead to side effects such as flushing, headache,
nausea, vomiting, abdominal cramps, and sweating. [69][70][70] These
symptoms are often called the disulfiram-like reaction. The proposed
mechanism of action for this interaction is that metronidazole can bind
to an enzyme that normally metabolizes alcohol. Binding to this enzyme
may impair the liver's ability to process alcohol for proper excretion. [71]

Pharmacology[edit]
Pharmacodynamics[edit]
See also: Alcohol intoxication Ethanol and GABAA
Receptors and Calcium channel blocker Ethanol
Ethanol acts in the central nervous system primarily by binding to the
GABAA receptor, increasing the effects of the
inhibitory neurotransmitter GABA (i.e., it is a positive allosteric
modulator).[72]
Ethanol is known to possess the following
direct pharmacodynamic actions (most important actions are bolded):[73]

GABAA receptor positive allosteric modulator (primarily of

subunit-containing receptors)
Glycine receptor positive and negative allosteric modulator

NMDA receptor negative allosteric modulator[74]

AMPA receptor negative allosteric modulator[74]

Kainate receptor negative allosteric modulator[74]

nACh receptor positive and negative allosteric modulator

5-HT3 receptor positive allosteric modulator

Glycine reuptake inhibitor[75]

Adenosine reuptake inhibitor[76]

L-type calcium channel blocker

GIRK channel opener

Some of its actions on ligand-gated ion channels, specifically the nACh

receptors and the glycine receptor, are dose-dependent, with
potentiation or inhibition occurring dependent on ethanol concentration.
This is because ethanol's effects on these channels are a summation of
positive and negative allosteric modulatory actions.[73]

Pharmacokinetics[edit]
The removal of ethanol from the human body, through oxidation
by alcohol dehydrogenase in the liver, is limited. Hence, the removal of
a large concentration of alcohol from blood may follow zero-order
kinetics. This means that alcohol leaves the body at a constant rate,
rather than having an elimination half-life.[9]
The rate-limiting steps for one substance may be in common with other
substances. As a result, the blood alcohol concentration can be used to
modify the rate of metabolism of methanol and ethylene glycol.
Methanol itself is not highly toxic, but its
metabolites formaldehyde and formic acid are; therefore, to reduce the
rate of production and concentration of these harmful metabolites,
ethanol can be ingested.[77] Ethylene glycol poisoning can be treated in
the same way.
Pure ethanol will irritate the skin and eyes.[78] Nausea, vomiting and
intoxication are symptoms of ingestion. Long-term use by ingestion can
result in serious liver damage.[79] Atmospheric concentrations above one
in a thousand are above the European Union Occupational exposure
limits.[79]
Metabolism[edit]
Main articles: Ethanol metabolism and Alcohol dehydrogenase
Ethanol within the human body is converted
into acetaldehyde by alcohol dehydrogenase and then into
the acetyl in acetyl CoA by acetaldehyde dehydrogenase. Acetyl CoA is
the final product of both carbohydrate and fat metabolism, where the
acetyl can be further used to produce energy or for biosynthesis. As
such, ethanol can be compared to an energy-bearing macronutrient,
yielding approximately 7 kcal per gram consumed. [80] However, the
product of the first step of this breakdown, acetaldehyde,[81] is more toxic
than ethanol. Acetaldehyde is linked to most of the clinical effects of
alcohol. It has been shown to increase the risk of developing cirrhosis of
the liver[82] and multiple forms of cancer.

During the metabolism of alcohol via the respective dehydrogenases,

NAD (Nicotinamide adenine dinucleotide) is converted into reduced
NAD. Normally, NAD is used to metabolise fats in the liver, and as such
alcohol competes with these fats for the use of NAD. Prolonged
exposure to alcohol means that fats accumulate in the liver, leading to
the term 'fatty liver'. Continued consumption (such as in alcoholism)
then leads to cell death in the hepatocytes as the fat stores reduce the
function of the cell to the point of death. These cells are then replaced
with scar tissue, leading to the condition called cirrhosis.
Alcohol and digestion[edit]
A part of ethyl alcohol is hydrophobic. This hydrophobic or lipophilic end
can diffuse across cells that line the stomach wall. In fact, alcohol is one
of the rare substances that can be absorbed in the stomach. Most food
substances are absorbed in the small intestine. However, even though
alcohol can be absorbed in the stomach, it is mostly absorbed in the
small intestine because the small intestine has a large surface area that
promotes absorption. Once alcohol is absorbed in the small intestine, it
delays the release of stomach contents from emptying into the small
intestine. Thus, alcohol can delay the rate of absorption of nutrients.
[83]
After absorption, alcohol reaches the liver where it is metabolized.
Breathalyzers
Alcohol that is not processed by the liver goes to the heart. The liver can
process only a certain amount of alcohol per unit time. Thus, when a
person drinks too much alcohol, more alcohol can reach the heart. In
the heart, alcohol reduces the force of heart contractions. Consequently,
the heart will pump less blood, lowering overall body blood pressure.
[50]
Also, blood that reaches the heart goes to the lungs to replenish
blood's oxygen concentration. It is at this stage that a person can
breathe out traces of alcohol.[50] This is the underlying principle of the
alcohol breath testing (or breathalyzers) to determine if a driver has
been drinking and driving.[84]
From the lungs, blood returns to the heart and will be distributed
throughout the body. Interestingly, alcohol increases levels of highdensity lipoproteins(HDLs), which carry cholesterol. [50] Alcohol is known
to make blood less likely to clot, reducing risk of heart attack and stroke.
This could be the reason that alcohol seems to produce health benefits
when consumed in moderate amounts.[85] Also, alcohol dilates blood
vessels. Consequently, a person will feel warmer, and his/her skin flush
and appear pink.[50]
Magnitude of effects[edit]
Some individuals have less effective forms of one or both of the
metabolizing enzymes, and can experience more severe symptoms
from ethanol consumption than others. However, those having
acquired alcohol tolerance have a greater quantity of these enzymes,
and metabolize ethanol more rapidly.[86]

Physical and chemical properties[edit]

Further information: Ethanol (data page)

Physical properties[edit]

Ethanol burning with its spectrum depicted

Ethanol is a volatile, colorless liquid that has a slight odor. It burns with
a smokeless blue flame that is not always visible in normal light.
The physical properties of ethanol stem primarily from the presence of
its hydroxyl group and the shortness of its carbon chain. Ethanol's
hydroxyl group is able to participate in hydrogen bonding, rendering it
more viscous and less volatile than less polar organic compounds of
similar molecular weight, such as propane.
Ethanol is slightly more refractive than water, having a refractive
index of 1.36242 (at =589.3 nm and 18.35 C or 65.03 F).[87]
The triple point for ethanol is 150 K at a pressure of 4.3 104 Pa.[88]

Solvent properties[edit]
Ethanol is a versatile solvent, miscible with water and with many organic
solvents, including acetic acid, acetone, benzene, carbon
tetrachloride, chloroform, diethyl ether, ethylene
glycol, glycerol, nitromethane,pyridine, and toluene.[87][89] It is also
miscible with light aliphatic hydrocarbons, such as pentane and hexane,
and with aliphatic chlorides such
as trichloroethane and tetrachloroethylene.[89]
Ethanol's miscibility with water contrasts with the immiscibility of longerchain alcohols (five or more carbon atoms), whose water miscibility
decreases sharply as the number of carbons increases.[90] The miscibility
of ethanol with alkanes is limited to alkanes up to undecane: mixtures
with dodecane and higher alkanes show a miscibility gap below a
certain temperature (about 13 C for dodecane[91]). The miscibility gap
tends to get wider with higher alkanes and the temperature for complete
miscibility increases.
Ethanol-water mixtures have less volume than the sum of their
individual components at the given fractions. Mixing equal volumes of
ethanol and water results in only 1.92 volumes of mixture. [87][92] Mixing

ethanol and water is exothermic, with up to 777 J/mol[93] being released

at 298 K.
Mixtures of ethanol and water form an azeotrope at about 89 mole-%
ethanol and 11 mole-% water[94] or a mixture of 95.6 percent ethanol by
mass (or about 97% alcohol by volume) at normal pressure, which boils
at 351K (78 C). This azeotropic composition is strongly temperatureand pressure-dependent and vanishes at temperatures below 303 K.[95]

Hydrogen bonding in solid ethanol at 186 C

Hydrogen bonding causes pure ethanol to be hygroscopic to the extent

that it readily absorbs water from the air. The polar nature of the
hydroxyl group causes ethanol to dissolve many ionic compounds,
notably sodium and potassium hydroxides, magnesium
chloride, calcium chloride, ammonium chloride, ammonium bromide,
and sodium bromide.[89] Sodium andpotassium chlorides are slightly
soluble in ethanol.[89] Because the ethanol molecule also has a nonpolar
end, it will also dissolve nonpolar substances, including most essential
oils[96] and numerous flavoring, coloring, and medicinal agents.
The addition of even a few percent of ethanol to water sharply reduces
the surface tension of water. This property partially explains the "tears of
wine" phenomenon. When wine is swirled in a glass, ethanol evaporates
quickly from the thin film of wine on the wall of the glass. As the wine's
ethanol content decreases, its surface tension increases and the thin
film "beads up" and runs down the glass in channels rather than as a
smooth sheet.

Flammability[edit]
An ethanol-water solution that contains 40% ABV (alcohol by volume)
will catch fire if heated to about 26 C (79 F) and if an ignition source is
applied to it. This is called its flash point.[97]The flash point of pure
ethanol is 16.60 C (61.88 F), less than average room temperature.
The flash points of ethanol concentrations from 10% ABV to 96% ABV
are shown below:[98]

10% 49 C (120 F)

20% 36 C (97 F)

30% 29 C (84 F)

40% 26 C (79 F)

50% 24 C (75 F)

60% 22 C (72 F)

70% 21 C (70 F)

80% 20 C (68 F)

90% 17 C (63 F)

96% 17 C (63 F)

Alcoholic beverages that have a low concentration of ethanol will burn if

sufficiently heated and an ignition source (such as an electric spark or a
match) is applied to them. For example, the flash point of ordinary wine
containing 12.5% ethanol is about 52 C (126 F).[99]
Dishes using burning alcohol for culinary effects are called Flamb.

Natural occurrence[edit]
Ethanol is a byproduct of the metabolic process of yeast. As such,
ethanol will be present in any yeast habitat. Ethanol can commonly be
found in overripe fruit.[100] Ethanol produced by symbiotic yeast can be
found in Bertam Palm blossoms. Although some animal species such as
the Pentailed Treeshrew exhibit ethanol-seeking behaviors, most show
no interest or avoidance of food sources containing ethanol. [101] Ethanol
is also produced during the germination of many plants as a result of
natural anerobiosis.[102] Ethanol has been detected in outer space,
forming an icy coating around dust grains in interstellar clouds.
[103]
Minute quantity amounts (average 196 ppb) of endogenous ethanol
and acetaldehyde were found in the exhaled breath of healthy
volunteers.[104] Auto-brewery syndrome, also known as gut fermentation
syndrome, is a rare medical condition in which intoxicating quantities of
ethanol are produced through endogenous fermentationwithin
the digestive system.[105][106]

Production[edit]

94% denatured ethanol sold in a bottle for household use

Ethanol is produced both as a petrochemical, through the hydration of

ethylene and, via biological processes, by fermenting sugars with yeast.
[107]
Which process is more economical depends on prevailing prices of
petroleum and grain feed stocks.

Ethylene hydration[edit]
Ethanol for use as an industrial feedstock or solvent (sometimes
referred to as synthetic ethanol) is made from petrochemical feed
stocks, primarily by the acid-catalyzed hydration of ethylene:
C
2H
4+H
2O CH
3CH
2OH
The catalyst is most commonly phosphoric acid,[108][109] adsorbed onto
a porous support such as silica gel or diatomaceous earth. This
catalyst was first used for large-scale ethanol production by
the Shell Oil Company in 1947.[110] The reaction is carried out in the
presence of high pressure steam at 300 C (572 F) where a 1.0:0.6
ethylene to steam ratio is maintained.[111][112] In the U.S., this process
was used on an industrial scale by Union Carbide Corporation and
others, but now only LyondellBasell uses it commercially.
In an older process, first practiced on the industrial scale in 1930 by
Union Carbide,[113] but now almost entirely obsolete, ethylene was
hydrated indirectly by reacting it with concentrated sulfuric acid to
produceethyl sulfate, which was hydrolyzed to yield ethanol and
regenerate the sulfuric acid:[114]
C
2H
4+H
2SO
4 CH
3CH
2SO
4H
CH
3CH
2SO
4H + H
2O CH
3CH
2OH + H
2SO
4

Fermentation[edit]
Main article: Ethanol fermentation
See also: Yeast in winemaking

Ethanol in alcoholic beverages and fuel is produced by

fermentation. Certain species
of yeast (e.g., Saccharomyces
cerevisiae) metabolizes sugar producing ethanol and
carbon dioxide. The chemical equations below summarize
the conversion:
C
6H
12O
6 2 CH
3CH
2OH + 2 CO2
C
12H
22O
11 + H
2O 4 CH
3CH
2OH + 4 CO2
Fermentation is the process of culturing yeast
under favorable thermal conditions to produce
alcohol. This process is carried out at around 35
40 C (95104 F). Toxicity of ethanol to yeast
limits the ethanol concentration obtainable by
brewing; higher concentrations, therefore, are
obtained by fortification or distillation. The most
ethanol-tolerant yeast strains can survive up to
approximately 18% ethanol by volume.
To produce ethanol from starchy materials such
as cereal grains, the starch must first be converted
into sugars. In brewing beer, this has traditionally
been accomplished by allowing the grain to
germinate, or malt, which produces
the enzymeamylase. When the malted grain
is mashed, the amylase converts the remaining
starches into sugars.
Cellulose[edit]
Main article: Cellulosic ethanol
Sugars for ethanol fermentation can be obtained
from cellulose. Deployment of this technology could
turn a number of cellulose-containing agricultural
by-products, such as corncobs, straw,
and sawdust, into renewable energy resources.
Other agricultural residues such as sugar cane
bagasse and energy crops such
as switchgrass may also be a sources of
fermentable sugars.[115]

Testing[edit]

Infrared reflection spectra of liquid ethanol, showing

the -OH band centered at ~3300 cm1 and C-H
bands at ~2950 cm1.

Near infrared spectrum of liquid ethanol.

Breweries and biofuel plants employ two methods

for measuring ethanol concentration. Infrared
ethanol sensors measure the vibrational frequency
of dissolved ethanol using the CH band at
2900 cm1. This method uses a relatively
inexpensive solid state sensor that compares the
CH band with a reference band to calculate the
ethanol content. The calculation makes use of
theBeer-Lambert law. Alternatively, by measuring
the density of the starting material and the density
of the product, using a hydrometer, the change in
specific gravity during fermentation indicates the
alcohol content. This inexpensive and indirect
method has a long history in the beer brewing
industry.

Purification[edit]
Distillation[edit]
Ethylene hydration or brewing produces an
ethanolwater mixture. For most industrial and fuel

uses, the ethanol must be purified. Fractional

distillation can concentrate ethanol to 95.6% by
volume (89.5 mole%). This mixture is
an azeotrope with a boiling point of 78.1 C
(172.6 F), and cannot be further purified by
distillation. Addition of an entraining agent, such
as benzene,cyclohexane, or heptane, allows a new
ternary azeotrope comprising the ethanol, water,
and the entraining agent to be formed. This lowerboiling ternary azeotrope is removed preferentially,
leading to water-free ethanol.[109]
At pressures less than atmospheric pressure, the
composition of the ethanol-water azeotrope shifts
to more ethanol-rich mixtures, and at pressures
less than 70 torr (9.333 kPa), there is no azeotrope,
and it is possible to distill absolute ethanol from an
ethanol-water mixture. While vacuum distillation of
ethanol is not presently economical, pressureswing distillation is a topic of current research. In
this technique, a reduced-pressure distillation first
yields an ethanol-water mixture of more than 95.6%
ethanol. Then, fractional distillation of this mixture
at atmospheric pressure distills off the 95.6%
azeotrope, leaving anhydrous ethanol at the
bottom.[citation needed]

Molecular sieves and desiccants[edit]

Molecular sieves can be used to selectively absorb
the water from the 95.6% ethanol solution.
Synthetic zeolite in pellet form can be used, as well
as a variety of plant-derived absorbents,
including cornmeal, straw, and sawdust. The
zeolite bed can be regenerated essentially an
unlimited number of times by drying it with a blast
of hot carbon dioxide. Cornmeal and other plantderived absorbents cannot readily be regenerated,
but where ethanol is made from grain, they are
often available at low cost. Absolute ethanol
produced this way has no residual benzene, and
can be used to fortify port and sherry in traditional
winery operations.
Apart from distillation, ethanol may be dried by
addition of a desiccant, such as molecular
sieves, cellulose, and cornmeal. The desiccants
can be dried and reused.[109]

Membranes and reverse osmosis[edit]

Membranes can also be used to separate ethanol
and water. Membrane-based separations are not
subject to the limitations of the water-ethanol
azeotrope because the separations are not based
on vapor-liquid equilibria. Membranes are often

used in the so-called hybrid membrane distillation

process. This process uses a pre-concentration
distillation column as first separating step. The
further separation is then accomplished with a
membrane operated either in vapor permeation or
pervaporation mode. Vapor permeation uses a
vapor membrane feed and pervaporation uses a
liquid membrane feed.

Other techniques[edit]
A variety of other techniques have been discussed,
including the following:[109]

Liquid-liquid extraction of ethanol from an

aqueous solution;
Extraction of ethanol from grain mash
by supercritical carbon dioxide;
Pervaporation;
Fractional freezing is also used to concentrate
fermented alcoholic solutions, such as
traditionally made Applejack (beverage);
Pressure swing adsorption.[116]

Grades of ethanol[edit]
Denatured alcohol[edit]
Main article: Denatured alcohol
Pure ethanol and alcoholic beverages are
heavily taxed as psychoactive drugs, but ethanol
has many uses that do not involve consumption by
humans. To relieve the tax burden on these uses,
most jurisdictions waive the tax when an agent has
been added to the ethanol to render it unfit to drink.
These include bittering agents such as denatonium
benzoate and toxins such as methanol, naphtha,
and pyridine. Products of this kind are
called denatured alcohol.[117][118]
Absolute alcohol[edit]
Absolute or anhydrous alcohol refers to ethanol
with a low water content. There are various grades
with maximum water contents ranging from 1% to a
few parts per million (ppm) levels. If azeotropic
distillation is used to remove water, it will contain
trace amounts of the material separation agent
(e.g. benzene).[119] Absolute alcohol is not intended
for human consumption. Absolute ethanol is used
as a solvent for laboratory and industrial
applications, where water will react with other
chemicals, and as fuel alcohol. Spectroscopic
ethanol is an absolute ethanol with a low

absorbance in ultraviolet and visible light, fit for use

as a solvent in ultraviolet-visible spectroscopy.[120]
Pure ethanol is classed as 200 proof in the U.S.,
equivalent to 175 degrees proof in the UK system.
[121]

Rectified spirits[edit]
Rectified spirit, an azeotropic composition of 96%
ethanol containing 4% water, is used instead of
anhydrous ethanol for various purposes. Wine
spirits are about 94% ethanol (188 proof). The
impurities are different from those in 95% (190
proof) laboratory ethanol.[122]

Reactions[edit]
For more details on this topic, see Alcohol.
Ethanol is classified as a primary alcohol, meaning
that the carbon its hydroxyl group attaches to has
at least two hydrogen atoms attached to it as well.
Many ethanol reactions occur at its hydroxyl group.

Ester formation[edit]
In the presence of acid catalysts, ethanol reacts
with carboxylic acids to produce ethyl esters and
water:
RCOOH + HOCH2CH3 RCOOCH2CH3 + H2O
This reaction, which is conducted on large
scale industrially, requires the removal of the
water from the reaction mixture as it is formed.
Esters react in the presence of an acid or base
to give back the alcohol and a salt. This
reaction is known as saponification because it
is used in the preparation of soap. Ethanol can
also form esters with inorganic acids. Diethyl
sulfate and triethyl phosphate are prepared by
treating ethanol with sulfur trioxide
and phosphorus pentoxiderespectively. Diethyl
sulfate is a useful ethylating agent in organic
synthesis. Ethyl nitrite, prepared from the
reaction of ethanol with sodium nitrite and
sulfuric acid, was formerly used as a diuretic.

Dehydration[edit]
Strong acid desiccants cause the partial
dehydration of ethanol to form diethyl ether and
other byproducts. If the dehydration
temperature exceeds around 160 C (320 F),
full dehydration will occur and ethylene will be
the main product.

2 CH3CH2OH CH3CH2OCH2CH3 + H2O (ca. 120 C)

CH3CH2OH H2C=CH2 + H2O (above 160 C)

Combustion[edit]
Complete combustion of ethanol
forms carbon dioxide and water:
C2H5OH (l) + 3 O2 (g) 2 CO2 (g) + 3 H2O (l); Hc =
1371 kJ/mol[123] = 29.8 kJ/g = 327 kcal/mol = 7.1 kcal/g
C2H5OH (l) + 3 O2 (g) 2 CO2 (g) + 3 H2O (g); Hc =
1236 kJ/mol = 26.8 kJ/g = 295.4 kcal/mol = 6.41 kcal/g[124]
Specific heat = 2.44 kJ/(kgK)

Acid-base
chemistry[edit]
Ethanol is a neutral molecule
and the pH of a solution of
ethanol in water is nearly 7.00.
Ethanol can be quantitatively
converted to its conjugate
base, the ethoxide ion
(CH3CH2O), by reaction with
an alkali metal such
as sodium:[90]
2 CH3CH2OH + 2 Na 2 CH3CH2ONa + H2
or a very strong base such
as sodium hydride:
CH3CH2OH + NaH CH3CH2ONa + H2
The acidity of water
and ethanol are nearly
the same, as indicated
by their pKa of 15.7
and 16 respectively.
Thus, sodium
ethoxide and sodium
hydroxide exist in an
equilibrium that is
closely balanced:
CH3CH2OH + NaOH

CH3CH2ONa + H2O

Halogenation[
edit]
Ethanol is not
used industrially
as a precursor to
ethyl halides, but
the reactions are
illustrative.
Ethanol reacts
with hydrogen

halides to
produce ethyl
halides such
as ethyl
chloride and ethyl
bromide via
an SN2 reaction:
CH3CH2OH + HCl CH3CH2Cl + H2O
These
reactions
require a
catalyst such
as zinc
chloride.[114] H
Br
requires reflux
ing with
a sulfuric
acid catalyst.
[114]
Ethyl
halides can, in
principle, also
be produced
by treating
ethanol with
more
specialized ha
logenating
agents, such
as thionyl
chloride or ph
osphorus
tribromide.[90]
[114]

CH3CH2OH + SOCl2 CH3CH2Cl + SO2 + HCl

Upon
treatment
with
halogens
in the
presence
of base,
ethanol
gives the
correspon
ding halof
orm (CHX
3, where X
= Cl, Br,
I). This
conversio

n is called
the halofo
rm
reaction.
[125]
" An
intermedi
ate in the
reaction
with
chlorine is
the aldeh
ydecalled
chloral:
4 Cl2 + CH3CH2OH CCl3CHO + 5 HCl

Oxid
atio
n[edi
t]
Ethan
ol can
be
oxidiz
ed
to ace
taldeh
yde a
nd
furthe
r
oxidiz
ed
to ace
tic
acid,
depe
nding
on
the
reage
nts
and
condit
ions.
[114]
Thi
s
oxidat
ion is
of no
impor
tance
indust

rially,
but in
the
huma
n
body,
these
oxidat
ion
reacti
ons
are
cataly
zed
by
theen
zyme
liver
alcoh
ol
dehyd
rogen
ase.
The
oxidat
ion
produ
ct of
ethan
ol,
acetic
acid,
is a
nutrie
nt for
huma
ns,
being
a
precu
rsor
to ace
tyl
CoA,
where
the
acetyl
group
can
be
spent
as
energ

y or
used
for
biosy
nthesi
s.

His
tory
[edit]
For
more
detail
s on
this
topic,
see D
istille
d
bever
age.
The f
erme
ntatio
n of
sugar
into
ethan
ol is
one
of the
earlie
st biot
echno
logies
emplo
yed
by
huma
ns.
The
intoxi
cating
effect
s of
ethan
ol
consu
mptio
n
have

been
know
n
since
ancie
nt
times.
Ethan
ol has
been
used
by
huma
ns
since
prehis
tory
as the
intoxi
cating
ingre
dient
of alc
oholic
bever
ages.
Dried
residu
e on
9,000
-yearold
potter
y
found
in
China
sugge
sts
that N
eolithi
c peo
ple
consu
med
alcoh
olic
bever
ages.
[126]

Altho
ugh di
stillati

on wa
s well
know
n by
the
early
Greek
s and
Arabs
, the
first
recor
ded
produ
ction
of
alcoh
ol
from
distill
ed
wine
was
by
the S
chool
of
Saler
no alc
hemis
ts in
the
12th
centu
ry.[127]
The
first to
menti
on
absol
ute
alcoh
ol, in
contr
ast
with
alcoh
olwater
mixtur
es,
was
Raym

ond
Lull.
[127]

In
1796,
Germ
anRussi
an
chemi
st
Johan
n
Tobia
s
Lowit
z
obtain
ed
pure
ethan
ol by
mixin
g
partial
ly
purifie
d
ethan
ol
(the
alcoh
olwater
azeot
rope)
with
an
exces
s of
anhyd
rous
alkali
and
then
distilli
ng
the
mixtur
e
over
low
heat.

Fr
ench
chemi
st Ant
oine
Lavoi
sier d
escrib
ed
ethan
ol as
a
comp
ound
of
carbo
n,
hydro
gen,
and
oxyge
n,
and in
1807
Nicol
asTho
dore
de
Saus
sure
deter
mined
ethan
ol's
chemi
cal
formu
la.[129]
[130]
Fift
y
years
later,
Archi
bald
Scott
Coup
er pu
blishe
d the
struct
ural
formu
[128]

la of
ethan
ol. It
was
one
of the
first
struct
ural
formu
las
deter
mined
.[131]
Ethan
ol
was
first
prepa
red
synth
eticall
y in
1825
by Mi
chael
Farad
ay.
He
found
that
sulfuri
c acid
could
absor
b
large
volum
es
of coa
l gas.
[132]
He
gave
the
resulti
ng
soluti
on to
Henry
Henn
ell, a
Britis
h

chemi
st,
who
found
in
1826
that it
contai
ned
"sulp
hovini
c
acid"
(ethyl
hydro
gen
sulfat
e).[133]
In
1828,
Henn
ell
and
the
Frenc
h
chemi
st
Geor
gesSimo
n
Srull
as
indep
ende
ntly
disco
vered
that
sulph
ovinic
acid
could
be
deco
mpos
ed
into
ethan
ol.[134]
[135]
Th
us, in

1825
Farad
ay
had
unwitt
ingly
disco
vered
that
ethan
ol
could
be
produ
ced
from
ethyle
ne (a
comp
onent
of
coal
gas)
by aci
dcataly
zed h
ydrati
on, a
proce
ss
simila
r to
curre
nt
indust
rial
ethan
ol
synth
esis.
[136]

Ethan
ol
was
used
as
lamp
fuel in
the
Unite
d
State

s as
early
as
1840,
but a
tax
levied
on
indust
rial
alcoh
ol
durin
g
the Ci
vil
War
made
this
use
uneco
nomic
al.
The
tax
was
repea
led in
1906.
[137]
Us
e as
an
auto
motiv
e fuel
dates
back
to
1908,
with
the F
ord
Model
T abl
e to
run
on pe
trol (g
asolin
e) or
ethan
ol.[138] I
t fuels

some
spirit
lamps
.
Ethan
ol
intend
ed for
indust
rial
use is
often
produ
ced
from
ethyle
ne.[139]
Ethan
ol has
wides
pread
use
as a
solve
nt of
subst
ances
intend
ed for
huma
n
conta
ct or
consu
mptio
n,
includ
ing
scent
s,
flavori
ngs,
colori
ngs,
and
medic
ines.
In
chemi
stry, it
is
both
a

solve
nt
and a
feedst
ock
for
the
synth
esis
of
other
produ
cts. It
has a
long
histor
y as a
fuel
for
heat
and
light,
and
more
recen
tly as
a fuel
for int
ernal
comb
ustion
engin
es.

Soc
iety
and
cult
ure[
edit]
For
more
detail
s on
this
topic,
see D
rinkin
g

cultur
e.
A
2002
study
found
41%
of
peopl
e
fatally
injure
d in
traffic
accid
ents
were
in
alcoh
ol
relate
d
crash
es.[140]
The
risk of
a
fatal c
ar
accid
ent in
creas
es
expon
entiall
y with
the
level
of
alcoh
ol in
the
driver'
s
blood.
[141]
Mo
st dru
nk
drivin
g law
s
gover
ning

the
accep
table
levels
in the
blood
while
drivin
g or
opera
ting
heavy
machi
nery
set
typica
l
upper
limits
of blo
od
alcoh
ol
conte
nt (B
AC)
betwe
en
0.02
%
and
0.08
%.
[citation
needed]

See
also
[edit]

1P
ro
p
a
n
ol
2,
2,
2Tr

ic
hl
or
o
et
h
a
n
ol
B
re
at
h
al
y
z
er
B
ut
a
n
ol
fu
el
E
th
a
n
ol
(d
at
a
p
a
g
e)
C
el
lu
lo
si
c
et
h
a
n
ol
c
o
m
m
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Ref
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t
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n
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r
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ff
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a

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d
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r
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R
e
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e
w
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t
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r
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o
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16. J
u
m
p
u
p
^
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e
bi
g,
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u
st
u
s
(
1
8
3
4
)
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e
b
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r
di
e
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o
n
st
it
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s
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et
h

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s
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r
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bi
n
d
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n
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e
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o
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r
a
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s
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s)
,
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r
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h
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:
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).
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p
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a
r
p
e
r,
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o
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gl
a
s.
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e
t
h
yl
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nl
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ty
m
ol
o
g
y
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ic
ti
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r
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u
m
p
u
p

^
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o
r
a
r
e
p
o
rt
o
n
th
e
1
8
9
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te
r
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h
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ic
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o
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at
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r
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e
e:
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m

str
on
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nr
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ck
ye
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by,
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rg
ea
nt,
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ee
t,
L;
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ig
ht,
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89
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he
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l
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nf
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tur
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od
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gli
sh
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m
str
on
g,
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nr
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.
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u
m
p
u
p
^
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E
D
;
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y

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o
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o
m
20. J
u
m
p
u
p
^
M
c
D
o
n
n
el
l
G
,
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u
s
s
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l
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;
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s
s
el
l
(
1
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9
9
).
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n
ti
s
e
p
ti
c
s
a
n

d
di
si
n
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n
ts
:
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iv
it
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li
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u
m
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al
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s
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.;
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c
k,
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.
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o
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li
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u
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u
m
p
u
p
^
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h
o
m
a
s,
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o
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u
m
p
u
p
^
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A
v
ai
la
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lit
y
o
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o
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r
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a
n
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ir
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-

2
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.
30. J
u
m
p
u
p
^
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e
el
,
M
.
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u
g
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st
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r
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l'
s
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h
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a
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u
m
p
u
p
^
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o
c
k
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ci
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e
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yi
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m
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p
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r
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n

,
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th
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al
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al
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p
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o
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.

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p
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s
G
lu
R
2
(
8
7
,
8
8
),
C
d
k
5
(
9
3
)
a
n
d
N
F
k
B
(
1
0
0
).
M
o
r
e
o
v
e
r,
m
a
n
y
o

f
t
h
e
s
e
m
ol
e
c
ul
a
r
c
h
a
n
g
e
s
id
e
n
tif
ie
d
a
r
e
n
o
w
di
r
e
ct
ly
li
n
k
e
d
t
o
t
h
e
st
r
u
ct
u
r
al
,
p
h
y
si

ol
o
gi
c
al
a
n
d
b
e
h
a
vi
o
r
al
c
h
a
n
g
e
s
o
b
s
e
r
v
e
d
f
ol
lo
w
in
g
c
h
r
o
ni
c
d
r
u
g
e
x
p
o
s
u
r
e
(
6
0
,

9
5
,
9
7
,
1
0
2
).
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e
w
fr
o
n
ti
e
r
s
o
f
r
e
s
e
a
r
c
h
in
v
e
st
ig
a
ti
n
g
t
h
e
m
ol
e
c
ul
a
r
r
ol
e
s
o
f

F
o
s

B
h
a
v
e
b
e
e
n
o
p
e
n
e
d
b
y
e
pi
g
e
n
e
ti
c
st
u
di
e
s,
a
n
d
r
e
c
e
n
t
a
d
v
a
n
c
e
s
h
a
v
e
ill
u
st
r
a
t
e
d

t
h
e
r
ol
e
o
f

F
o
s
B
a
ct
in
g
o
n
D
N
A
a
n
d
hi
st
o
n
e
s,
tr
ul
y
a
s
a

m
ol
e
c
ul
a
r
s
w
it
c
h

(
3
4
).
A
s
a
c

o
n
s
e
q
u
e
n
c
e
o
f
o
u
r
i
m
p
r
o
v
e
d
u
n
d
e
r
st
a
n
di
n
g
o
f

F
o
s
B
in
a
d
di
ct
io
n
,
it
is
p
o
s
si
bl
e
t
o

e
v
al
u
a
t
e
t
h
e
a
d
di
ct
iv
e
p
o
t
e
n
ti
al
o
f
c
u
rr
e
n
t
m
e
di
c
a
ti
o
n
s
(
1
1
9
),
a
s
w
el
l
a
s
u
s
e
it
a
s
a

bi
o
m
a
r
k
e
r
f
o
r
a
s
s
e
s
si
n
g
t
h
e
e
ffi
c
a
c
y
o
f
t
h
e
r
a
p
e
u
ti
c
in
t
e
r
v
e
n
ti
o
n
s
(
1
2
1
,
1
2
2

,
1
2
4
).
S
o
m
e
o
f
t
h
e
s
e
p
r
o
p
o
s
e
d
in
t
e
r
v
e
n
ti
o
n
s
h
a
v
e
li
m
it
a
ti
o
n
s
(
1
2
5
)
o
r
a
r
e
in
t

h
ei
r
in
f
a
n
c
y
(
7
5
).
H
o
w
e
v
e
r,
it
is
h
o
p
e
d
t
h
a
t
s
o
m
e
o
f
t
h
e
s
e
p
r
el
i
m
in
a
r
y
fi
n
di
n
g
s
m
a

y
le
a
d
t
o
in
n
o
v
a
ti
v
e
tr
e
a
t
m
e
n
ts
,
w
hi
c
h
a
r
e
m
u
c
h
n
e
e
d
e
d
in
a
d
di
ct
io
n
.
63. J
u
m
p
u
p
^
N
e
st

le
r
E
J
(
D
e
c
e
m
b
e
r
2
0
1
3
).
"
C
el
lu
la
r
b
a
si
s
o
f
m
e
m
o
r
y
f
o
r
a
d
di
ct
io
n
".
D
ia
lo
g
u
e
s
C
li
n
N
e
u

r
o
s
ci
1
5
(
4
):
4
3
1

4
4
3
.
P
M
C
3
8
9
8
6
8
1
.
P
M
I
D
2
4
4
5
9
4
1
0
.
D
E
S
P
I
T
E
T
H
E
I
M
P
O
R
T
A
N

C
E
O
F
N
U
M
E
R
O
U
S
P
S
Y
C
H
O
S
O
C
I
A
L
F
A
C
T
O
R
S
,
A
T
I
T
S
C
O
R
E
,
D
R
U
G
A
D
D
I
C
T
I
O
N
I
N
V
O

L
V
E
S
A
B
I
O
L
O
G
I
C
A
L
P
R
O
C
E
S
S
:
t
h
e
a
bi
lit
y
o
f
r
e
p
e
a
t
e
d
e
x
p
o
s
u
r
e
t
o
a
d
r
u
g
o
f
a
b

u
s
e
t
o
in
d
u
c
e
c
h
a
n
g
e
s
in
a
v
ul
n
e
r
a
bl
e
b
r
ai
n
t
h
a
t
d
ri
v
e
t
h
e
c
o
m
p
ul
si
v
e
s
e
e
ki
n
g
a
n
d

t
a
ki
n
g
o
f
d
r
u
g
s,
a
n
d
lo
s
s
o
f
c
o
n
tr
ol
o
v
e
r
d
r
u
g
u
s
e
,
t
h
a
t
d
e
fi
n
e
a
st
a
t
e
o
f
a
d
di
ct
io
n

.
..
.
A
la
r
g
e
b
o
d
y
o
f
lit
e
r
a
t
u
r
e
h
a
s
d
e
m
o
n
st
r
a
t
e
d
t
h
a
t
s
u
c
h

F
o
s
B
in
d
u
ct
io
n
in
D
1
-

ty
p
e
N
A
c
n
e
u
r
o
n
s
in
c
r
e
a
s
e
s
a
n
a
ni
m
al
's
s
e
n
si
ti
vi
ty
t
o
d
r
u
g
a
s
w
el
l
a
s
n
a
t
u
r
al
r
e
w
a
r

d
s
a
n
d
p
r
o
m
o
t
e
s
d
r
u
g
s
el
fa
d
m
in
is
tr
a
ti
o
n
,
p
r
e
s
u
m
a
bl
y
t
h
r
o
u
g
h
a
p
r
o
c
e
s
s
o
f
p
o

si
ti
v
e
r
ei
n
f
o
r
c
e
m
e
n
t
64. J
u
m
p
u
p
^
R
o
bi
s
o
n
A
J,
N
e
st
le
r
E
J
(
N
o
v
e
m
b
e
r
2
0
1
1
).
"
T
r
a
n
s

c
ri
p
ti
o
n
al
a
n
d
e
pi
g
e
n
e
ti
c
m
e
c
h
a
ni
s
m
s
o
f
a
d
di
ct
io
n
".
N
a
t.
R
e
v.
N
e
u
r
o
s
ci
.
1
2
(
1
1
):
6
2
3


6
3
7
.
d
oi
:
1
0
.
1
0
3
8
/
n
r
n
3
1
1
1
.
P
M
C
3
2
7
2
2
7
7
.
P
M
I
D
2
1
9
8
9
1
9
4
.

F
o
s
B
h
a
s
b
e
e

n
li
n
k
e
d
di
r
e
ct
ly
t
o
s
e
v
e
r
al
a
d
di
ct
io
n
r
el
a
t
e
d
b
e
h
a
vi
o
r
s
..
.
I
m
p
o
rt
a
n
tl
y,
g
e
n
e
ti
c
o
r

vi
r
al
o
v
e
r
e
x
p
r
e
s
si
o
n
o
f

J
u
n
D
,
a
d
o
m
in
a
n
t
n
e
g
a
ti
v
e
m
u
t
a
n
t
o
f
J
u
n
D
w
hi
c
h
a
n
t
a

g
o
ni
z
e
s

F
o
s
B
a
n
d
o
t
h
e
r
A
P
1
m
e
di
a
t
e
d
tr
a
n
s
c
ri
p
ti
o
n
al
a
ct
iv
it
y,
in
t
h
e
N
A
c
o
r
O
F

C
bl
o
c
k
s
t
h
e
s
e
k
e
y
e
ff
e
ct
s
o
f
d
r
u
g
e
x
p
o
s
u
r
e
14,
22

.
T
hi
s
in
di
c
a
t
e
s
t
h
a
t

F
o
s
B
is
b
o
t
24

h
n
e
c
e
s
s
a
r
y
a
n
d
s
u
ffi
ci
e
n
t
f
o
r
m
a
n
y
o
f
t
h
e
c
h
a
n
g
e
s
w
r
o
u
g
h
t
in
t
h
e
b
r
ai
n
b
y
c
h
r

o
ni
c
d
r
u
g
e
x
p
o
s
u
r
e
.

F
o
s
B
is
al
s
o
in
d
u
c
e
d
in
D
1
ty
p
e
N
A
c
M
S
N
s
b
y
c
h
r
o
ni
c
c
o
n
s
u
m

p
ti
o
n
o
f
s
e
v
e
r
al
n
a
t
u
r
al
r
e
w
a
r
d
s,
in
cl
u
di
n
g
s
u
c
r
o
s
e
,
hi
g
h
f
a
t
f
o
o
d
,
s
e
x,
w
h
e
el
r
u

n
ni
n
g
,
w
h
e
r
e
it
p
r
o
m
o
t
e
s
t
h
a
t
c
o
n
s
u
m
p
ti
o
n
14,
26

.
T
hi
s
i
m
pl
ic
a
t
e
s

F
o
s
B
in
t
h
e
r
e
g
30

ul
a
ti
o
n
o
f
n
a
t
u
r
al
r
e
w
a
r
d
s
u
n
d
e
r
n
o
r
m
al
c
o
n
di
ti
o
n
s
a
n
d
p
e
r
h
a
p
s
d
u
ri
n
g
p
a
t
h
ol
o

gi
c
al
a
d
di
ct
iv
e
li
k
e
st
a
t
e
s.
..
.

F
o
s
B
s
e
r
v
e
s
a
s
o
n
e
o
f
t
h
e
m
a
st
e
r
c
o
n
tr
ol
p
r
o
t
ei
n
s
g

o
v
e
r
ni
n
g
t
hi
s
st
r
u
ct
u
r
al
pl
a
st
ic
it
y.
65. J
u
m
p
u
p
^
L
ai
z
u
r
e
,
S
.
C
.;
M
a
n
d
r
el
l,
T
.;
G
a
d
e
s,
N
.
M

.;
P
a
r
k
e
r,
R
.
B
.
(
2
0
0
3
).
"
C
o
c
a
e
t
h
yl
e
n
e
m
e
t
a
b
ol
is
m
a
n
d
in
t
e
r
a
ct
io
n
w
it
h
c
o
c
ai
n
e
a

n
d
e
t
h
a
n
ol
:
R
ol
e
o
f
c
a
r
b
o
x
yl
e
st
e
r
a
s
e
s
".
D
r
u
g
m
e
t
a
b
ol
is
m
a
n
d
di
s
p
o
si
ti
o
n
:
t
h
e
bi

ol
o
gi
c
al
f
a
t
e
o
f
c
h
e
m
ic
al
s
3
1
(
1
):
1
6

2
0
.
d
oi
:
1
0
.
1
1
2
4
/
d
m
d
.
3
1
.
1
.
1
6
.
P
M
I
D
1
2
4

8
5
9
4
8
.
66. J
u
m
p
u
p
^
S
a
k
al
o
,
V
.
S
.;
R
o
m
a
n
e
n
k
o
,
A
.
M
.;
K
li
m
e
n
k
o
,
I.
A
.;
P
e
r
si
d
s
ki
,
I
u

V
(
1
9
8
8
).
"
E
ff
e
ct
s
o
f
c
h
e
m
o
t
h
e
r
a
p
y
o
n
r
e
gi
o
n
al
m
e
t
a
st
a
s
e
s
o
f
n
o
n
s
e
m
in
o
m
a
t
o

u
s
t
u
m
o
r
s
o
f
t
h
e
t
e
st
is
".
V
o
p
r
o
s
y
o
n
k
ol
o
gi
i
3
4
(
1
0
):
1
2
1
9

2
4
.
P
M
I
D
3
1
8
8
4
2
4
.

67. J
u
m
p
u
p
^
L
u
k
a
s,
S
c
o
tt
E
.;
O
r
o
z
c
o
,
S
a
r
a
(
2
0
0
1
).
"
E
t
h
a
n
ol
in
c
r
e
a
s
e
s
pl
a
s
m
a

9
t

e
tr
a
h
y
d
r
o
c
a
n
n
a
bi
n
ol
(
T
H
C
)
le
v
el
s
a
n
d
s
u
bj
e
ct
iv
e
e
ff
e
ct
s
a
ft
e
r
m
a
ri
h
u
a
n
a
s
m
o
ki
n
g
in

h
u
m
a
n
v
ol
u
n
t
e
e
r
s
".
D
r
u
g
a
n
d
A
lc
o
h
ol
D
e
p
e
n
d
e
n
c
e
6
4
(
2
):
1
4
3

9
.
d
oi
:
1
0
.
1
0
1
6
/

S
0
3
7
6
8
7
1
6
(
0
1
)
0
0
1
1
8
1
.
P
M
I
D
1
1
5
4
3
9
8
4
.
68. J
u
m
p
u
p
^
R
e
p
c
hi
n
s
k
y
C
(
e
d.
)
(
2

0
1
2
).
C
o
m
p
e
n
di
u
m
of
p
h
a
r
m
a
c
e
ut
ic
al
s
a
n
d
s
p
e
ci
al
ti
e
s,
O
tt
a
w
a:
C
a
n
a
di
a
n
P
h
a
r
m
a
ci
st
s
A

s
s
o
ci
at
io
n.
[full
cita
tion
nee
ded
]

69. J
u
m
p
u
p
^
A
r
o
n
s
o
n
,
I.
K
.;
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u
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84. J
u
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u
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Ext
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link
s[edi
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Look up alcohol or ethanolin
Wiktionary, the free dictionary.
Wikimedia Commons has media
related to Ethanol.

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