In chemistry, an alcohol is any organic compound in which the hydroxyl
functional group (–OH) is bound to a saturated carbon atom. The
term alcohol originally referred to the primary alcohol ethanol (ethyl
alcohol), which is used as a drug and is the main alcohol present in
The suffix -ol appears in the
IUPAC chemical name of all substances
where the hydroxyl group is the functional group with the highest
priority; in substances where a higher priority group is present the
prefix hydroxy- will appear in the International Union of Pure and
Chemistry (IUPAC) name. The suffix -ol in non-systematic names
(such as paracetamol or cholesterol) also typically indicates that the
substance includes a hydroxyl functional group and, so, can be termed
an alcohol. But many substances, particularly sugars (examples glucose
and sucrose) contain hydroxyl functional groups without using the
suffix. An important class of alcohols, of which methanol and ethanol
are the simplest members is the saturated straight chain alcohols, the
general formula for which is CnH2n+1OH.
2.2 Systematic names
2.3 Common names
Alkyl chain variations in alcohols
2.3.2 Simple alcohols
2.3.3 Higher alcohols
5 Physical and chemical properties
6 Occurrence in nature
7.1 Ziegler and oxo processes
7.2 Hydration reactions
7.3 Biological routes
8.2 Nucleophilic substitution
9 See also
12 External links
Rhazes (854 CE – 925 CE), was a Persian polymath,
physician, alchemist, and philosopher who discovered numerous
compounds and chemicals including "alcohol" by developing several
chemical instruments and methods of distillation.
The word "alcohol" is from the Arabic kohl (Arabic: الكحل,
translit. al-kuḥl), a powder used as an eyeliner.
Al- is the
Arabic definite article, equivalent to the in English.
originally used for the very fine powder produced by the sublimation
of the natural mineral stibnite to form antimony trisulfide Sb
3, hence the essence or "spirit" of this substance. It was used as an
antiseptic, eyeliner, and cosmetic. The meaning of alcohol was
extended to distilled substances in general, and then narrowed to
ethanol, when "spirits" was a synonym for hard liquor.
Bartholomew Traheron, in his 1543 translation of John of Vigo,
introduces the word as a term used by "barbarous" (Moorish) authors
for "fine powder." Vigo wrote: "the barbarous auctours use alcohol, or
(as I fynde it sometymes wryten) alcofoll, for moost fine poudre."
The 1657 Lexicon Chymicum, by William Johnson glosses the word as
"antimonium sive stibium." By extension, the word came to refer to
any fluid obtained by distillation, including "alcohol of wine," the
distilled essence of wine.
Libavius in Alchymia (1594) refers to "vini
alcohol vel vinum alcalisatum". Johnson (1657) glosses alcohol vini as
"quando omnis superfluitas vini a vino separatur, ita ut accensum
ardeat donec totum consumatur, nihilque fæcum aut phlegmatis in fundo
remaneat." The word's meaning became restricted to "spirit of wine"
(the chemical known today as ethanol) in the 18th century and was
extended to the class of substances so-called as "alcohols" in modern
chemistry after 1850.
The term ethanol was invented 1892, combining the word ethane with the
"-ol" ending of "alcohol".
IUPAC nomenclature is used in scientific publications and where
precise identification of the substance is important, especially in
cases where the relative complexity of the molecule does not make such
a systematic name unwieldy. In the
IUPAC system, in naming simple
alcohols, the name of the alkane chain loses the terminal "e" and adds
"ol", e.g., as in "methanol" and "ethanol". When necessary, the
position of the hydroxyl group is indicated by a number between the
alkane name and the "ol": propan-1-ol for CH
2OH, propan-2-ol for CH
3. If a higher priority group is present (such as an aldehyde, ketone,
or carboxylic acid), then the prefix "hydroxy" is used, e.g., as
in 1-hydroxy-2-propanone (CH
Some examples of simple alcohols and how to name them
A primary alcohol
A secondary alcohol
A secondary alcohol
A primary alcohol
A tertiary alcohol
In cases where the OH functional group is bonded to an sp2 carbon on
an aromatic ring the molecule is known as a phenol, and is named using
IUPAC rules for naming phenols.
In other less formal contexts, an alcohol is often called with the
name of the corresponding alkyl group followed by the word "alcohol",
e.g., methyl alcohol, ethyl alcohol.
Propyl alcohol may be n-propyl
alcohol or isopropyl alcohol, depending on whether the hydroxyl group
is bonded to the end or middle carbon on the straight propane chain.
As described under systematic naming, if another group on the molecule
takes priority, the alcohol moiety is often indicated using the
Alcohols are then classified into primary, secondary (sec-, s-), and
tertiary (tert-, t-), based upon the number of carbon atoms connected
to the carbon atom that bears the hydroxyl functional group. (The
respective numeric shorthands 1°, 2°, and 3° are also sometimes
used in informal settings.) The primary alcohols have general
formulas RCH2OH. The simplest primary alcohol is methanol (CH3OH), for
which R=H, and the next is ethanol, for which R=CH3, the methyl group.
Secondary alcohols are those of the form RR'CHOH, the simplest of
which is 2-propanol (R=R'=CH3). For the tertiary alcohols the general
form is RR'R"COH. The simplest example is tert-butanol
(2-methylpropan-2-ol), for which each of R, R', and R" is CH3. In
these shorthands, R, R', and R" represent substituents, alkyl or other
attached, generally organic groups.
isopropyl alcohol, rubbing alcohol
butanol, butyl alcohol
pentanol, amyl alcohol
Unsaturated aliphatic alcohols
2 - (2-propyl)-5-methyl-cyclohexane-1-ol
Alkyl chain variations in alcohols
Short-chain alcohols have alkyl chains of 1–3 carbons. Medium-chain
alcohols have alkyl chains of 4–7 carbons. Long-chain alcohols (also
known as fatty alcohols) have alkyl chains of 8–21 carbons, and very
long-chain alcohols have alkyl chains of 22 carbons or longer.
"Simple alcohols" appears to be a completely undefined term. However,
simple alcohols are often referred to by common names derived by
adding the word "alcohol" to the name of the appropriate alkyl group.
For instance, a chain consisting of one carbon (a methyl group, CH3)
with an OH group attached to the carbon is called "methyl alcohol"
while a chain of two carbons (an ethyl group, CH2CH3) with an OH group
connected to the CH2 is called "ethyl alcohol." For more complex
IUPAC nomenclature must be used.
Simple alcohols, in particular ethanol and methanol, possess
denaturing and inert rendering properties, leading to their use as
anti-microbial agents in medicine, pharmacy, and industry.[citation
Encyclopædia Britannica states, "The higher alcohols—those
containing 4 to 10 carbon atoms—are somewhat viscous, or oily, and
they have heavier fruity odours. Some of the highly branched alcohols
and many alcohols containing more than 12 carbon atoms are solids at
Like ethanol, butanol can be produced by fermentation processes.
Saccharomyces yeast are known to produce these higher alcohols at
temperatures above 75 °F (24 °C). The bacterium
Clostridium acetobutylicum can feed on cellulose to produce butanol on
an industrial scale.
Total recorded alcohol per capita consumption (15+), in litres of pure
Alcohol has a long history of several uses worldwide. It is found in
alcoholic beverages sold to adults, as fuel, and also has many
scientific, medical, and industrial uses. The term alcohol-free is
often used to describe a product that does not contain alcohol.
Alcoholic drinks, typically containing 3–40% alcohol by volume, have
been produced and consumed by humans since pre-historic times. Natural
fermentation also produces trace amounts of other alcohols such as
2-methyl-2-butanol and γ-hydroxybutyric acid (GHB), which have
psychoactive effects similar to alcohol when used as a drug.
Antifreeze commonly includes a 50% v/v (by volume) solution of
ethylene glycol in water.
Ethanol can be used as an antiseptic to disinfect the skin
before injections are given, often along with iodine.
Ethanol-based soaps are becoming common in restaurants and are
convenient because they do not require drying due to the volatility of
Alcohol based gels have become common as hand
Alcohol fuel: Some alcohols, mainly ethanol and methanol, can be used
as fuel. Fuel performance can be increased in forced induction
internal combustion engines by injecting alcohol into the air intake
after the turbocharger or supercharger has pressurized the air. This
cools the pressurized air, providing a denser air charge, which allows
for more fuel, and therefore more power.
Alcohol is often used as a preservative for biological
specimens in the fields of science and medicine.
Hydroxyl groups (-OH), found in alcohols, are polar and
therefore hydrophilic (water loving) but their carbon chain portion is
non-polar which make them hydrophobic. The molecule increasingly
becomes overall more nonpolar and therefore less soluble in the polar
water as the carbon chain becomes longer.
Methanol has the
shortest carbon chain of all alcohols (one carbon atom) followed by
ethanol (two carbon atoms.) Alcohols have applications in industry and
science as reagents or solvents. Because of its relatively low
toxicity compared with other alcohols and ability to dissolve
non-polar substances, ethanol can be used as a solvent in medical
drugs, perfumes, and vegetable essences such as vanilla. In organic
synthesis, alcohols serve as versatile intermediates.
This section needs more medical references for verification or relies
too heavily on primary sources. Please review the contents of the
section and add the appropriate references if you can. Unsourced or
poorly sourced material may be challenged and removed. (June 2014)
Ball-and-stick model of tert-Amyl alcohol, which is 20 times more
intoxicating than ethanol and like all tertiary alcohols, cannot be
metabolised to toxic
aldehydes.[better source needed][better source needed]
Ethanol is thought to cause harm partly as a result of direct damage
DNA caused by its metabolites.
Most significant of the possible long-term effects of ethanol. In
addition, in pregnant women it may cause fetal alcohol syndrome.
Ethanol's toxicity is largely caused by its primary metabolite,
acetaldehyde (systematically ethanal) and secondary
metabolite, acetic acid. Many primary alcohols are
metabolized into aldehydes then to carboxylic acids whose toxicities
are similar to acetaldehyde and acetic acid.
Metabolite toxicity is reduced in rats fed N-acetylcysteine
Although the mechanism is unclear, a meta-analysis of 572 studies have
shown increased cancer risk from consumption of ethanol.
Tertiary alcohols cannot be metabolized into aldehydes and as a
result they cause no hangover or toxicity through this mechanism.
Some secondary and tertiary alcohols are less poisonous than ethanol,
because the liver is unable to metabolize them into toxic
by-products. This makes them more suitable for pharmaceutical use
as the chronic harms are lower.
Ethchlorvynol and tert-amyl
alcohol are tertiary alcohols which have seen both medicinal and
Other alcohols are substantially more poisonous than ethanol, partly
because they take much longer to be metabolized and partly because
their metabolism produces substances that are even more toxic.
Methanol (wood alcohol), for instance, is oxidized to formaldehyde and
then to the poisonous formic acid in the liver by alcohol
dehydrogenase and formaldehyde dehydrogenase enzymes, respectively;
accumulation of formic acid can lead to blindness or death.
Likewise, poisoning due to other alcohols such as ethylene glycol or
diethylene glycol are due to their metabolites, which are also
produced by alcohol dehydrogenase.
Methanol itself, while poisonous (LD50 5628 mg/kg, oral,
rat), has a much weaker sedative effect than ethanol.
Isopropyl alcohol is oxidized to form acetone by alcohol dehydrogenase
in the liver, but has occasionally been abused by alcoholics, leading
to a range of adverse health
effects.[better source needed][better source needed]
An effective treatment to prevent toxicity after methanol or ethylene
glycol ingestion is to administer ethanol.
Alcohol dehydrogenase has a
higher affinity for ethanol, thus preventing methanol from binding and
acting as a substrate. Any remaining methanol will then have time to
be excreted through the kidneys.
Physical and chemical properties
Alcohols have an odor that is often described as "biting" and as
"hanging" in the nasal passages.
Ethanol has a slightly sweeter (or
more fruit-like) odor than the other alcohols.
In general, the hydroxyl group makes the alcohol molecule polar. Those
groups can form hydrogen bonds to one another and to other compounds
(except in certain large molecules where the hydroxyl is protected by
steric hindrance of adjacent groups). This hydrogen bonding means
that alcohols can be used as protic solvents. Two opposing solubility
trends in alcohols are: the tendency of the polar OH to promote
solubility in water, and the tendency of the carbon chain to resist
it. Thus, methanol, ethanol, and propanol are miscible in water
because the hydroxyl group wins out over the short carbon chain.
Butanol, with a four-carbon chain, is moderately soluble because of a
balance between the two trends. Alcohols of five or more carbons such
as pentanol and higher are effectively insoluble in water because of
the hydrocarbon chain's dominance. All simple alcohols are miscible in
organic solvents.
Because of hydrogen bonding, alcohols tend to have higher boiling
points than comparable hydrocarbons and ethers. The boiling point of
the alcohol ethanol is 78.29 °C, compared to 69 °C for the
hydrocarbon hexane (a common constituent of gasoline), and
34.6 °C for diethyl ether.
Alcohols, like water, can show either acidic or basic properties at
the -OH group. With a pKa of around 16-19, they are, in general,
slightly weaker acids than water, but they are still able to react
with strong bases such as sodium hydride or reactive metals such as
sodium. The salts that result are called alkoxides, with the general
formula RO− M+.
Meanwhile, the oxygen atom has lone pairs of nonbonded electrons that
render it weakly basic in the presence of strong acids such as
sulfuric acid. For example, with methanol:
Alcohols can be oxidised to give aldehydes, ketones or carboxylic
acids, or they can be dehydrated to alkenes. They can react with
carboxylic acids to form ester compounds, and they can (if activated
first) undergo nucleophilic substitution reactions. The lone pairs of
electrons on the oxygen of the hydroxyl group also makes alcohols
nucleophiles. For more details, see the reactions of alcohols section
As one moves from primary to secondary to tertiary alcohols with the
same backbone, the hydrogen bond strength, the boiling point, and the
acidity typically decrease.
Occurrence in nature
Ethanol occurs naturally as 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.
Methanol is produced naturally in the anaerobic metabolism of many
varieties of bacteria, and is commonly present in small amounts in the
Alcohols have been found outside the
Solar System at low densities in
star-forming regions of interstellar space.
Ziegler and oxo processes
In the Ziegler process, linear alcohols are produced from ethylene and
triethylaluminium followed by oxidation and hydrolysis. An
idealized synthesis of
1-octanol is shown:
Al(C2H5)3 + 9 C2H4 → Al(C8H17)3
Al(C8H17)3 + 3 O + 3 H2O → 3 HOC8H17 + Al(OH)3
The process generates a range of alcohols that are separated by
Many higher alcohols are produced by hydroformylation of alkenes
followed by hydrogenation. When applied to a terminal alkene, as is
common, one typically obtains a linear alcohol:
RCH=CH2 + H2 + CO → RCH2CH2CHO
RCH2CH2CHO + 3 H2 → RCH2CH2CH2OH
Such processes give fatty alcohols, which are useful for detergents.
Low molecular weight alcohols of industrial importance are produced by
the addition of water to alkenes. Ethanol, isopropanol, 2-butanol, and
tert-butanol are produced by this general method. Two implementations
are employed, the direct and indirect methods. The direct method
avoids the formation of stable intermediates, typically using acid
catalysts. In the indirect method, the alkene is converted to the
sulfate ester, which is subsequently hydrolyzed. The direct hydration
using ethylene (ethylene hydration) or other alkenes from cracking
of fractions of distilled crude oil.
Hydration is also used industrially to produce the diol ethylene
glycol from ethylene oxide.
Ethanol is obtained by fermentation using glucose produced from sugar
from the hydrolysis of starch, in the presence of yeast and
temperature of less than 37 °C to produce ethanol. For instance,
such a process might proceed by the conversion of sucrose by the
enzyme invertase into glucose and fructose, then the conversion of
glucose by the enzyme complex zymase into ethanol (and carbon
Several of the benign bacteria in the intestine use fermentation as a
form of anaerobic metabolism. This metabolic reaction produces ethanol
as a waste product, just like aerobic respiration produces carbon
dioxide and water. Thus, human bodies contain some quantity of alcohol
endogenously produced by these bacteria. In rare cases, this can be
sufficient to cause "auto-brewery syndrome" in which intoxicating
quantities of alcohol are produced.
Primary alkyl halides react with aqueous NaOH or KOH mainly to primary
alcohols in nucleophilic aliphatic substitution. (Secondary and
especially tertiary alkyl halides will give the elimination (alkene)
product instead). Grignard reagents react with carbonyl groups to
secondary and tertiary alcohols. Related reactions are the Barbier
reaction and the Nozaki-Hiyama reaction.
Aldehydes or ketones are reduced with sodium borohydride or lithium
aluminium hydride (after an acidic workup). Another reduction by
aluminiumisopropylates is the Meerwein-Ponndorf-Verley reduction.
Noyori asymmetric hydrogenation
Noyori asymmetric hydrogenation is the asymmetric reduction of
Alkenes engage in an acid catalysed hydration reaction using
concentrated sulfuric acid as a catalyst that gives usually secondary
or tertiary alcohols. The hydroboration-oxidation and
oxymercuration-reduction of alkenes are more reliable in organic
Alkenes react with NBS and water in halohydrin formation
reaction. Amines can be converted to diazonium salts, which are then
The formation of a secondary alcohol via reduction and hydration is
Alcohols behave as weak acids, undergoing deprotonation, but strong
bases are required. The deprotonation reaction to produce an alkoxide
salt is performed with a strong base such as sodium hydride or sodium
2 R-OH + 2 NaH → 2 R-O−Na+ + 2 H2
2 R-OH + 2 Na → 2 R-O−Na+ + H2
Water is similar in pKa to many alcohols, so with sodium hydroxide an
equilibrium exists, which usually lies to the left:
R-OH + NaOH ⇌ R-O−Na+ + H2O (equilibrium to the left)
The acidity of alcohols is strongly affected by solvation. In the gas
phase, alcohols are more acidic than is water.
The OH group is not a good leaving group in nucleophilic substitution
reactions, so neutral alcohols do not react in such reactions.
However, if the oxygen is first protonated to give R−OH2+, the
leaving group (water) is much more stable, and the nucleophilic
substitution can take place. For instance, tertiary alcohols react
with hydrochloric acid to produce tertiary alkyl halides, where the
hydroxyl group is replaced by a chlorine atom by unimolecular
nucleophilic substitution. If primary or secondary alcohols are to be
reacted with hydrochloric acid, an activator such as zinc chloride is
needed. In alternative fashion, the conversion may be performed
directly using thionyl chloride.
Alcohols may, likewise, be converted to alkyl bromides using
hydrobromic acid or phosphorus tribromide, for example:
3 R-OH + PBr3 → 3 RBr + H3PO3
Barton-McCombie deoxygenation an alcohol is deoxygenated to an
alkane with tributyltin hydride or a trimethylborane-water complex in
a radical substitution reaction.
Alcohols are themselves nucleophilic, so R−OH2+ can react with ROH
to produce ethers and water in a dehydration reaction, although this
reaction is rarely used except in the manufacture of diethyl ether.
More useful is the E1 elimination reaction of alcohols to produce
alkenes. The reaction, in general, obeys Zaitsev's Rule, which states
that the most stable (usually the most substituted) alkene is formed.
Tertiary alcohols eliminate easily at just above room temperature, but
primary alcohols require a higher temperature.
This is a diagram of acid catalysed dehydration of ethanol to produce
A more controlled elimination reaction is the
Chugaev elimination with
carbon disulfide and iodomethane.
To form an ester from an alcohol and a carboxylic acid the reaction,
known as Fischer esterification, is usually performed at reflux with a
catalyst of concentrated sulfuric acid:
R-OH + R'-COOH → R'-COOR + H2O
In order to drive the equilibrium to the right and produce a good
yield of ester, water is usually removed, either by an excess of H2SO4
or by using a Dean-Stark apparatus. Esters may also be prepared by
reaction of the alcohol with an acid chloride in the presence of a
base such as pyridine.
Other types of ester are prepared in a similar manner – for
example, tosyl (tosylate) esters are made by reaction of the alcohol
with p-toluenesulfonyl chloride in pyridine.
Primary alcohols (R-CH2-OH) can be oxidized either to aldehydes
(R-CHO) or to carboxylic acids (R-CO2H), while the oxidation of
secondary alcohols (R1R2CH-OH) normally terminates at the ketone
(R1R2C=O) stage. Tertiary alcohols (R1R2R3C-OH) are resistant to
The direct oxidation of primary alcohols to carboxylic acids normally
proceeds via the corresponding aldehyde, which is transformed via an
aldehyde hydrate (R-CH(OH)2) by reaction with water before it can be
further oxidized to the carboxylic acid.
Mechanism of oxidation of primary alcohols to carboxylic acids via
aldehydes and aldehyde hydrates
Reagents useful for the transformation of primary alcohols to
aldehydes are normally also suitable for the oxidation of secondary
alcohols to ketones. These include
Collins reagent and Dess-Martin
periodinane. The direct oxidation of primary alcohols to carboxylic
acids can be carried out using potassium permanganate or the Jones
Index of alcohol-related articles
IUPAC Gold Book. Retrieved 16 December 2013.
^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book")
(1997). Online corrected version: (2006–) "Alcohols".
^ Hitti, Philip K. (1977). History of the Arabs from the earliest
times to the present (10th ed.). London: Macmillan. p. 365.
ISBN 978-0-333-09871-4. The most notable medical authors who
followed the epoch of the great translators were Persian in
nationality but Arab in language: 'Ali al-Tabari, al-Razi, 'Ali
ibn-al-'Abbas al-Majusi and ibn-Sina.
^ Robinson, Victor (1944), The story of medicine, New York: New Home
^ Porter, Dorothy (2005), Health, civilization, and the state: a
history of public health from ancient to modern times, New York:
Routledge (published 1999), p. 25, ISBN 0-415-20036-9 ;
Reviewed in Vaughan P (2000). "Health, civilization and the state: a
history of public health from ancient to modern times". Bull World
Health Organ. 78 (9): 1170. PMC 2560849 .
^ Lohninger, H. "VIAS Encyclopedia: Etymology of the Word "Alcohol"".
^ a b "alcohol, n." OED Online. Oxford University Press, September
2016. Web. 15 November 2016.
^ Lexicon Chymicum
^ Proc. Chem. Soc. 8 July 1892, page 128 "As ol is indicative of an OH
derivative, there seems no reason why the simple word acid should not
connote carboxyl, and why al should not connote COH; the names ethanol
ethanal and ethanoic acid or simply ethane acid would then stand for
the OH, COH and COOH derivatives of ethane."
^ a b William Reusch. "Alcohols". VirtualText of Organic Chemistry.
Archived from the original on 19 September 2007. Retrieved 14
^ Organic chemistry
IUPAC nomenclature. Alcohols Rule C-201.
Chemistry Nomenclature Rule C-203: Phenols
^ "How to name organic compounds using the
www.chem.uiuc.edu. THE DEPARTMENT OF CHEMISTRY AT THE UNIVERSITY OF
ILLINOIS. Retrieved 14 November 2016.
^ Reusch, William. "Nomenclature of Alcohols". chemwiki.ucdavis.edu/.
Retrieved 17 March 2015.
^ "MetaCyc Compound Class: a short-chain alcohol". Retrieved 31
^ "Molecule Gallery - Alcohols". Retrieved 31 December 2013.
^ "alcohol (chemical compound)". Encyclopædia Britannica. Retrieved
31 December 2013.
^ Zverlov, W; Berezina, O; Velikodvorskaya, GA; Schwarz, WH (August
2006). "Bacterial acetone and butanol production by industrial
fermentation in the Soviet Union: use of hydrolyzed agricultural waste
for biorefinery". Applied Microbiology Technology. 71 (5): 587–97.
doi:10.1007/s00253-006-0445-z. PMID 16685494.
^ "Global Status Report on
Alcohol 2004" (PDF). Retrieved 28 November
^ Mahon, Connie R.; Lehman, Donald C.; Manuselis, George (2014-03-25).
Textbook of Diagnostic Microbiology - E-Book. Elsevier Health
Sciences. ISBN 9780323292627.
^ "Alcohols, Phenols, Thiols, and Ethers".
Chemistry - Louisiana Tech
University. Retrieved 31 December 2013.
^ Hans Brandenberger; Robert A. A. Maes, eds. (1997). Analytical
Toxicology for Clinical, Forensic and Pharmaceutical Chemists.
p. 401. ISBN 3-11-010731-7.
^ D. W. Yandell; et al. (1888). "Amylene hydrate, a new hypnotic". The
American Practitioner and News. Louisville KY: John P. Morton &
Co. 5: 88–89.
^ Carey, Francis. Organic
Chemistry (4 ed.). ISBN 0072905018.
Retrieved 5 February 2013.
^ Brooks PJ (1997). "
DNA repair, and alcohol toxicity-a
review". Alcoholism: Clinical and Experimental Research. 21 (6):
^ a b Fowkes, Steven (13 December 1996). "Living with alcohol". Smart
Drug News. 5. Retrieved 2 March 2012.
^ a b Melton, Lisa. "What's your poison" (PDF). New Scientist.
Archived from the original on 21 February 2012. Retrieved 10 February
^ Maxwell CR, Spangenberg RJ, Hoek JB, Silberstein SD, Oshinsky ML
(2010). Skoulakis, Efthimios M. C., ed. "Acetate causes alcohol
hangover headache in rats". PLoS ONE. 5 (12): e15963.
PMC 3013144 . PMID 21209842.
^ Ramachandra Murty, B (1 October 2004). "The Biochemistry of Alcohol
Toxicity" (PDF). Archived (PDF) from the original on 20 August 2012.
Retrieved 21 February 2012.
^ Cassarett, Lewis; Doull, John (1986). Toxicology: The Basic Science
of Poisons (3rd ed.). pp. 648–653.
^ Ozaras R, Tahan V, Aydin S, Uzun H, Kaya S, Senturk H (2003).
"N-acetylcysteine attenuates alcohol-induced oxidative stress in the
rat". World Journal of Gastroenterology. 9 (1): 125–128.
doi:10.3748/wjg.9.125. PMID 12508366.
^ Sprince, H; Parker, CM; Smith, GG; Gonzales, LJ (1974). "Protection
against acetaldehyde toxicity in the rat by l-cysteine, thiamin and
l-2-Methylthiazolidine-4-carboxylic acid". Agents and Actions. 4 (2):
125–130. doi:10.1007/BF01966822. PMID 4842541.
^ Bagnardi V, Rota M, Botteri E, Tramacere I, Islami F, Fedirko V,
Scotti L, Jenab M, Turati F, Pasquali E, Pelucchi C, Galeone C,
Bellocco R, Negri E, Corrao G, Boffetta P, La Vecchia C (2015).
Alcohol consumption and site-specific cancer risk: a comprehensive
dose-response meta-analysis". British Journal of Cancer. 112 (3):
580–93. doi:10.1038/bjc.2014.579. PMC 4453639 .
^ http://www.otago.ac.nz/news/news/otago617874.html[full citation
^ Collins AS, Sumner SC, Borghoff SJ, Medinsky MA (1999). "A
physiological model for tert-amyl methyl ether and tert-amyl alcohol:
Hypothesis testing of model structures". Toxicological Sciences. 49
(1): 15–28. doi:10.1093/toxsci/49.1.15. PMID 10367338.
^ "oxidation of alcohols". chemguide.co.uk.
^ Hirsh HL, Orsinger WH (1952). "Methylparafynol--a new type hypnotic.
Preliminary report on its therapeutic efficacy and toxicity". American
practitioner and digest of treatment. 3 (1): 23–26.
^ Adriani, John (1962). The
Chemistry and Physics of Anesthesia.
Second Edition. Illinois: Thomas Books. pp. 273–274.
^ a b Schep LJ, Slaughter RJ, Vale JA, Beasley DM (30 September 2009).
"A seaman with blindness and confusion". BMJ. 339: b3929.
doi:10.1136/bmj.b3929. PMID 19793790.
^ Brent J (May 2009). "Fomepizole for ethylene glycol and methanol
poisoning". N. Engl. J. Med. 360 (21): 2216–23.
doi:10.1056/NEJMct0806112. ISSN 0028-4793.
^ Schep LJ, Slaughter RJ, Temple WA, Beasley DM (July 2009).
Diethylene glycol poisoning". Clin Toxicol. 47 (6): 525–35.
doi:10.1080/15563650903086444. ISSN 1556-3650.
^ "ChemIDplus Advanced - Chemical information with searchable
synonyms, structures, and formulas". nih.gov.
^ Wiernikowski A, Piekoszewski W, Krzyzanowska-Kierepka E, Gomułka E
(1997). "Acute oral poisoning with isopropyl alcohol in alcoholics".
Przeglad lekarski. 54 (6): 459–63. PMID 9333902.
^ Mańkowski W, Klimaszyk D, Krupiński B (2000). "How to
differentiate acute isopropanol poisoning from ethanol intoxication?
– a case report". Przeglad lekarski. 57 (10): 588–90.
^ Zimmerman HE, Burkhart KK, Donovan JW (1999). "
Ethylene glycol and
methanol poisoning: diagnosis and treatment". Journal of Emergency
Nursing. 25 (2): 116–20. doi:10.1016/S0099-1767(99)70156-X.
^ Lobert S (2000). "Ethanol, isopropanol, methanol, and ethylene
glycol poisoning". Critical care nurse. 20 (6): 41–7.
^ Majerza I, Natkaniec I (2006). "Experimental and theoretical IR, R,
and INS spectra of 2,2,4,4-tetramethyl-3-t-butyl-pentane-3-ol".
Journal of Molecular Structure. 788 (1–3): 93–101.
^ Sfetcu, Nicolae (2014). Health & Drugs Disease, Prescription
& Medication. North Carolina: Lulu.com.
^ Charnley, S. B.; Kress, M. E.; Tielens, A. G. G. M.; Millar, T. J.
(1995). "Interstellar Alcohols". Astrophysical Journal. 448: 232.
^ Giant cloud of space alcohol found labnews.co.uk/
^ a b Jürgen Falbe, Helmut Bahrmann, Wolfgang Lipps, Dieter Mayer
"Alcohols, Aliphatic" in Ullmann's Encyclopedia of Chemical Technology
Wiley-VCH Verlag; Weinheim, 2002. doi:10.1002/14356007.a01_279
^ Lodgsdon J.E. (1994). "Ethanol". In Kroschwitz J.I. Encyclopedia of
Chemical Technology. 9 (4th ed.). New York: John Wiley & Sons.
p. 820. ISBN 0-471-52677-0.
^ P. Geertinger MD; J. Bodenhoff; K. Helweg-Larsen; A. Lund (1
September 1982). "Endogenous alcohol production by intestinal
fermentation in sudden infant death". Zeitschrift für Rechtsmedizin.
Springer-Verlag. 89 (3): 167–172. doi:10.1007/BF01873798.
^ Logan BK, Jones AW (July 2000). "Endogenous ethanol 'auto-brewery
syndrome' as a drunk-driving defence challenge". Medicine, science,
and the law. 40 (3): 206–15. PMID 10976182.
^ Cecil Adams (20 October 2006). "Designated drunk: Can you get
intoxicated without actually drinking alcohol?". The Straight Dope.
Retrieved 27 February 2013.
^ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry:
Reactions, Mechanisms, and Structure (6th ed.), New York:
Wiley-Interscience, ISBN 0-471-72091-7
Metcalf, Allan A. (1999). The World in So Many Words. Houghton
Mifflin. ISBN 0-395-95920-9.
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