From Wikipedia, the free encyclopedia
The hydroxyl (OH) functional group in an alcohol molecule
.^ When they present their original data relating to the methanol content of French wines (range 14-265 ppm) or when the methanol content of any alcoholic beverage is given, the ration of methanol to ethanol is also presented.
.^ METHANOL Methanol (methyl alcohol, wood alcohol), a poisonous substance (60), is added as a component during the manufacture of aspartame (47).
^ Abstract] "Many of the signs and symptoms of intoxication due to methanol ingestion are not specific to methyl alcohol.
^ Methyl alcohol produces the Methyl alcohol syndrome, consistently , only in humans and no other test animal, including monkeys (42, 54).
The suffix
-ol appears in the
IUPAC chemical name of all alcohols.
Simple alcohols
The most commonly used alcohol is
ethanol,
C2H5OH, with the
ethane backbone.
.^ There are approximately 80,000 chemicals in common industrial use today (almost none of which existed before World War II).
^ An alcoholic consuming 1500 calories a day from alcoholic sources alone may consume between 0 and 600 mg of methanol each day depending on his choice of beverages (Table 1).
^ Thirty-five billion pounds of toxic industrial byproducts certainly seems like a significant quantity of toxicants to be adding to the environment each year, the environment which human beings and other life forms need in order to live, to live well, and to reproduce.
.^ METHANOL Methanol (methyl alcohol, wood alcohol), a poisonous substance (60), is added as a component during the manufacture of aspartame (47).
^ Although some forms of mercury are hazardous, the mercury in amalgam is chemically bound to the other metals to make it stable and therefore safe for use in dental applications.
^ Some aspartame victims need this surgery even after they stop 'using', because aspartame harms the synovial fluid that bathes the joints.
Ethanol in this form is known generally as
denatured alcohol; when methanol is used, it may be referred to as
methylated spirits ("Meths") or "surgical spirits".
.^ METHANOL Methanol (methyl alcohol, wood alcohol), a poisonous substance (60), is added as a component during the manufacture of aspartame (47).
^ Therefore if a liter of a high methanol content orange juice is consumed, with 33 mg/liter of methanol and a 20/1 ration of ethanol/methanol, only one molecule of methanol in 180 will be metabolized into dangerous metabolites until the majority of the ethanol has been cleared from the bloodstream.
^ The wood alcohol (methanol) is widely distributed throughout the body including brain, muscle, fat and nervous tissue.
.^ This study admitted one datum that showed accumulation of formaldehye in the midbrain from an acute toxicity dose of methanol, and widespread accumulation of formic acid in five tissues.
^ ETHANOL AND FOLIC ACID The importance of ethanol as an antidote to methanol toxicity in humans is very well established in the literature (46, 55).
^ Ethanol, the classic antidote for methanol toxicity, is found in natural food sources of methanol at concentrations 5 to 500,000 times that of the toxin (Table 1).
[1]
.^ When they present their original data relating to the methanol content of French wines (range 14-265 ppm) or when the methanol content of any alcoholic beverage is given, the ration of methanol to ethanol is also presented.
^ Of the wines they tested, the ratio associated with the highest methanol content (265 ppm) indicates over 262 times as much ethanol present as methanol.
^ Cigarette smoke, a known coronary risk factor, contains four times as much methanol as formaldehyde and only traces of ethanol.
Like ethanol, they can be produced by fermentation processes. (However, the fermenting agent is a bacterium,
Clostridium acetobutylicum, that feeds on
cellulose, not sugars like the
Saccharomyces yeast that produces ethanol.)
Nomenclature
Systematic names
In the
IUPAC system, the name of the alkane chain loses the terminal "e" and adds "ol", e.g.
.^ Of the wines they tested, the ratio associated with the highest methanol content (265 ppm) indicates over 262 times as much ethanol present as methanol.
.^ Each row corresponds to a different sequence, the sequence name is stored in the first column, while other columns contain residue numbers in the selected alignment positions.- ICM Language Reference : Functions 9 October 2009 5:33 UTC www.molsoft.com [Source type: Reference]
If a higher priority group is present (such as an
aldehyde,
ketone or
carboxylic acid), then it is necessary to use the prefix "hydroxy",
[2] for example: 1-hydroxy-2-propanone (CH
3COCH
2OH).
Some examples of simple alcohols and how to name them
The IUPAC nomenclature is used in scientific publications and where precise identification of the substance is important. 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.
.^ An alcoholic consuming 1500 calories a day from alcoholic sources alone may consume between 0 and 600 mg of methanol each day depending on his choice of beverages (Table 1).
^ Alcoholics may average much more, with a potential range of between 0 and 600 mg/day, depending on the source and in some cases the quality of their beverages (15).
Alcohols are classified into
primary,
secondary and
tertiary, based upon the number of carbon atoms connected to the carbon atom that bears the hydroxyl group. Namely, the primary alcohols have general formulas RCH
2OH; secondary ones are RR'CHOH; and tertiary ones are RR'R"COH, where R, R'and R" stand for alkyl groups. Ethanol and
n-propyl alcohol are primary alcohols; isopropyl alcohol is a secondary one. The prefixes
sec- (or
s-) and
tert- (or
t-), conventionally in italics, may be used before the alkyl group's name to distinguish secondary and tertiary alcohols, respectively, from the primary one. For example, isopropyl alcohol is occasionally called
sec-propyl alcohol, and the tertiary alcohol (CH
3)
3COH, or 2-methylpropan-2-ol in IUPAC nomenclature, is commonly known as
tert-butyl alcohol or
tert-butanol.
Common Names
| Chemical Formula |
IUPAC Name |
Common Name |
| Monohydric alcohols |
| CH3OH |
Methanol |
Wood alcohol |
| C2H5OH |
Ethanol |
Grain alcohol |
| C5H11OH |
Pentanol |
Amyl alcohol |
| C16H33OH |
Hexadecan-1-ol |
Cetyl alcohol |
| Polyhydric alcohols |
| C2H4(OH)2 |
Ethane-1 ,2-diol |
Ethylene glycol |
| C3H5(OH)3 |
Propane-1 ,2,3-triol |
Glycerin |
| C4H6(OH)4 |
Butane-1 ,2,3,4-tetraol |
Erythritol |
| C5H7(OH)5 |
Pentane-1 ,2,3,4,5-pentol |
Xylitol |
| C6H8(OH)6 |
Hexane-1 ,2,3,4,5,6-hexol |
Mannitol, Sorbitol |
| C7H9(OH)7 |
Heptane-1 ,2,3,4,5,6,7-heptol |
Volemitol |
| Unsaturated aliphatic alcohols |
| C3H5OH |
Prop-2-ene-1-ol |
Allyl alcohol |
| C10H17OH |
3,7-Dimethylocta-2,6-dien-1-ol |
Geraniol |
| C3H3OH |
Prop-2-in-1-ol |
Propargyl alcohol |
| Alicyclic alcohols |
| C6H6(OH)6 |
Cyclohexane-1 ,2,3,4,5,6-geksol |
Inositol |
| C10H19OH |
2 - (2-propyl)-5-methyl-cyclohexane-1-ol |
Menthol |
Etymology
The word
alcohol appears in English in the 16th century, loaned via French from medical
Latin, ultimately from the
Arabic الكحل (
al-kuḥl, "the
kohl, a powder used as an eyeliner").
The current Arabic name for alcohol is الكحول al-kuḥūl, re-introduced from western usage.
Bartholomew Traheron in his 1543 translation of
John of Vigo introduces the word as a term used by "barbarous" (
Moorish) authors for "fine powder":
- the barbarous auctours use alcohol, or (as I fynde it sometymes wryten) alcofoll, for moost fine poudre.
William Johnson in his 1657
Lexicon Chymicum 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) has
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" (
ethanol) in the 18th century, and was again extended to the family of substances so called in modern chemistry from 1850.
Physical and chemical properties
Alcohols have an odor that is often described as “biting” and as “hanging” in the nasal passages.
The
hydroxyl group generally 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
[3]). 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 of the carbon chain to resist it.
.^ This dose of methanol is thus 20 mg from each can, while the EPA limit for drinking water is 7.8 mg daily.
^ [Thus, 600 mg aspartame gives 66 mg methanol, which is 8.5 times the EPA daily limit for drinking water of 7.8 mg daily methanol.
Butanol, with a four-carbon chain, is moderately soluble because of a balance between the two trends. Alcohols of five or more carbons (
Pentanol and higher) are effectively insoluble in water because of the hydrocarbon chain's dominance. All simple alcohols are miscible in organic solvents.
Alcohols, like water, can show either acidic or basic properties at the O-H group. With a
pKa of around 16-19 they are generally 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:
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.
Applications
.^ The inhibitory effect is a linear function of the log of the ethyl alcohol concentration, with a 72% inhibition rate at only a 0.01 molar concentration of ethanol (2, 46).
^ When they present their original data relating to the methanol content of French wines (range 14-265 ppm) or when the methanol content of any alcoholic beverage is given, the ration of methanol to ethanol is also presented.
^ Aspartame is a widely used artificial sweetener added to many soft beverages and its usage is increasing in health-conscious societies.
.^ An alcoholic consuming 1500 calories a day from alcoholic sources alone may consume between 0 and 600 mg of methanol each day depending on his choice of beverages (Table 1).
^ There is information "from highly reliable sources" that they frequently consumed aspartame in the form of both beverages and a tabletop sweetener.
^ When they present their original data relating to the methanol content of French wines (range 14-265 ppm) or when the methanol content of any alcoholic beverage is given, the ration of methanol to ethanol is also presented.
A 50% v/v solution of
ethylene glycol in water is commonly used as an
antifreeze.
Alcohols have applications in industry and science as reagents or
solvents.
.^ But low doses of chemicals, because they are legally considered to be at negligible levels, have no such notification or labeling requirements.
In
organic synthesis, alcohols serve as versatile intermediates.
Ethanol can be used as an antiseptic to disinfect the skin before injections are given, often along with iodine.
.^ But low doses of chemicals, because they are legally considered to be at negligible levels, have no such notification or labeling requirements.
Alcohol is also used as a
preservative for specimens.
Production
Industrially alcohols are produced in several ways:
Endogenous
Several of the benign bacteria in the intestine use
fermentation as a form of
anaerobic respiration.
.^ This means the possibility of metabolism in the GI tract to methanol, formaldehyde, formic acid, and, finally, carbon dioxide and water, was bypassed.
.^ Methyl alcohol produces the Methyl alcohol syndrome, consistently , only in humans and no other test animal, including monkeys (42, 54).
Laboratory synthesis
Several methods exist for the preparation of alcohols in the laboratory.
Substitution
Reduction
Hydrolysis
The formation of a secondary alcohol via reduction and hydration is shown:

Reactions
Deprotonation
Alcohols can behave as weak acids, undergoing
deprotonation. The deprotonation reaction to produce an
alkoxide salt is either performed with a strong base such as sodium hydride or
n-butyllithium, or with sodium or potassium metal.
- 2 R-OH + 2 NaH → 2 R-O-Na+ + 2H2↑
- 2 R-OH + 2Na → 2R-O−Na + H2
- E.g. 2 CH3CH2-OH + 2 Na → 2 CH3-CH2-O−Na + H2
- R-OH + NaOH <=> R-O-Na+ + H2O (equilibrium to the left)
It should be noted, though, that the bases used to deprotonate alcohols are strong themselves.
.^ In this vein, the patients complain of a sensitivity (both olfactory and respiratory) to environments containing low concentrations of HCHO and other chemicals.
The acidity of alcohols is also affected by the overall stability of the alkoxide ion.
Electron-withdrawing groups attached to the carbon containing the hydroxyl group will serve to stabilize the alkoxide when formed, thus resulting in greater acidity.
.^ Although some forms of mercury are hazardous, the mercury in amalgam is chemically bound to the other metals to make it stable and therefore safe for use in dental applications.
This will result in a scenario whereby the unstable alkoxide ion formed will tend to accept a proton to reform the original alcohol.
Nucleophilic substitution
- 3 R-OH + PBr3 → 3 RBr + H3PO3
Dehydration
Alcohols are themselves nucleophilic, so R−OH
2+ 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 generally 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
ethene:
A more controlled elimination reaction is the
Chugaev elimination with carbon disulfide and iodomethane.
Esterification
- 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 H
2SO
4 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 similarly- for example
tosyl (tosylate) esters are made by reaction of the alcohol with p-
toluenesulfonyl chloride in pyridine.
Oxidation
.^ Alcohol dehydrogenase is the primary enzyme for the oxidation of methanol to formaldehyde, and this oxidation reaction is the rate-limiting step in the metabolism of methanol.
Tertiary alcohols (R
1R
2R
3C-OH) are resistant to oxidation.
.^ Alcohol dehydrogenase is the primary enzyme for the oxidation of methanol to formaldehyde, and this oxidation reaction is the rate-limiting step in the metabolism of methanol.
Mechanism of oxidation of primary alcohols to carboxylic acids via aldehydes and aldehyde hydrates
.^ Alcohol dehydrogenase is the primary enzyme for the oxidation of methanol to formaldehyde, and this oxidation reaction is the rate-limiting step in the metabolism of methanol.
These include
Collins reagent and
Dess-Martin periodinane.
.^ Alcohol dehydrogenase is the primary enzyme for the oxidation of methanol to formaldehyde, and this oxidation reaction is the rate-limiting step in the metabolism of methanol.
Toxicity
.^ With the reduced demand for liquid fuel, it is possible that we could fuel most cars with the ethanol WE ALREADY PRODUCE...- John Stossel : The Many Myths of Ethanol - Townhall.com 27 January 2010 23:50 UTC townhall.com [Source type: FILTERED WITH BAYES]
^ How the writer could have determined within one day that no one would suffer any long-term or irreversible adverse effects was not explained.
^ Most importantly, delocalization effects are corrected so that ; artifact-free imaging of the perimeter of a sample is possible.- Fritz-Haber-Institut der Max-Planck-Gesellschaft Berlin 18 May 2010 14:42 UTC www.fhi-berlin.mpg.de [Source type: Academic]
Additionally, in pregnant women, it causes
fetal alcohol syndrome.
.^ When they present their original data relating to the methanol content of French wines (range 14-265 ppm) or when the methanol content of any alcoholic beverage is given, the ration of methanol to ethanol is also presented.
^ An alcoholic consuming 1500 calories a day from alcoholic sources alone may consume between 0 and 600 mg of methanol each day depending on his choice of beverages (Table 1).
.^ (In addition, the mixtures of these chemicals which bioaccumulate within an organism in low doses may have toxic effects many times those of any one chemical.
^ This high ethanol to methanol ratio, even at these low ethanol concentrations, may have some protective effect.
^ The letters also tell the Bushes to get off the drugs as soon as possible since they may have side effects such as procainemide, which slows the heart beat.
Depending upon the dose and the regularity of its consumption, ethanol can cause acute respiratory failure or death. Because ethanol impairs judgment in humans, it can be a catalyst for reckless or irresponsible behavior. The
LD50 of
ethanol in rats is 10.3 g/kg.
[6]
.^ Everything, even water, they say, is toxic in some dose.
^ METHANOL Methanol (methyl alcohol, wood alcohol), a poisonous substance (60), is added as a component during the manufacture of aspartame (47).
^ Although methanol itself is not highly toxic, it is metabolized by alcohol dehydrogenase to formaldehyde and subsequently to formic acid (Fig.
.^ The inhibition of alcohol dehydrogenase is fundamental to the treatment of methanol poisoning.
^ In the body, methanol is oxidized to formaldehyde and formic acid; both of these metabolites are toxic."
^ Formaldehyde was detected only in the blood of Monkey B, while formate was found in 8 and 10, respectively, of the 10 fluid and tissue samples in Monkeys B and C. For instance, the lowest value of formate, except for zero-time blood, for each monkey was in the midbrain, 2.16 mmol/kg for Monkey B (24 times the detection limit for the chromatropic acid method) and 1.02 mmol/kg (1.3 times the detection for the dimedon method) for Monkey C. This shows accumulation of formate in liver, kidney, optic nerve, cerebrum, and midbrain.
[7] .^ Methyl alcohol produces the Methyl alcohol syndrome, consistently , only in humans and no other test animal, including monkeys (42, 54).
^ The inhibition of alcohol dehydrogenase is fundamental to the treatment of methanol poisoning.
^ We performed a multicenter study to evaluate fomepizole, an inhibitor of alcohol dehydrogenase, in the treatment of patients with methanol poisoning.
[8][9] .^ However, soon after ingestion by a creature, its 11% methanol component is released and quickly metabolized into the potent, cumulative, mutagenic toxicants, formaldehyde and formic acid.
^ ETHANOL AND FOLIC ACID The importance of ethanol as an antidote to methanol toxicity in humans is very well established in the literature (46, 55).
^ Ethanol, the classic antidote for methanol toxicity, is found in natural food sources of methanol at concentrations 5 to 500,000 times that of the toxin (Table 1).
.^ Alcoholic polyneuropathy (36) or multiple peripheral neuritis (21) differs symptomatically from the methanol induced syndrome only in its first and often exclusive affinity for legs.
^ When they present their original data relating to the methanol content of French wines (range 14-265 ppm) or when the methanol content of any alcoholic beverage is given, the ration of methanol to ethanol is also presented.
^ However, remember this is not drinking alcohol, but methanol (wood alcohol) -- thus his complaints about his vision and his memory.
.^ Ethanol inhibits metabolism of methanol and allows the body time for clearance of the toxin through the lungs and kidneys (40, 46).
[7][10][11]
.^ This high ethanol to methanol ratio, even at these low ethanol concentrations, may have some protective effect.
^ The timely administration of ethanol is still considered a vital part of methanol poisoning management (11, 12, 19, 20, 50).
^ Of the wines they tested, the ratio associated with the highest methanol content (265 ppm) indicates over 262 times as much ethanol present as methanol.
.^ Unfortunately, the records documenting these chemical dispersals sometimes disappear or are lost, so that the toxicants remaining in an environment can last much longer than their records.
^ The minimum lethal dose of methanol in the rat, rabbit, and dog is 9, 5, 7, and 8 g/kg, respectively (43); ethyl alcohol is more toxic than methanol to these test animals (43).
^ Alcoholics have a much higher incidence of cancer and other degenerative diseases, none of which can be attributed to ethanol alone (56).
[12][13] .^ According to FDA regulations, compounds added to foods that are found to cause some adverse health effect at a particular usage level are actually permitted in foods only at much lower levels.
^ Even habitual leg crossing is found to be a cause of serious problems for some patients, and also aerobic exercise.
^ Alcoholics may average much more, with a potential range of between 0 and 600 mg/day, depending on the source and in some cases the quality of their beverages (15).
[16] .^ If formaldehyde were to somehow stay locked in those products it might not result in adverse human health effects, but it does not stay locked in.
^ Before we do that, however, we will, in Chapter One, look at the array of adverse human health effects associated with exposure to environmental toxicants.
^ We will instead be more concerned with the long-term adverse health effects that people might experience as a result of such an exposure.
[19]
Occurrence in nature
Alcohol has been found outside the Solar system. It can be found in low densities in star and planetary system forming regions of space.
See
See also
References
- ^ Vale A (2007). "Methanol". Medicine 35 (12): 633–4. doi:10.1016/j.mpmed.2007.09.014.
- ^ a b William Reusch. "Alcohols". VirtualText of Organic Chemistry. http://www.cem.msu.edu/~reusch/VirtualText/alcohol1.htm#alcnom. Retrieved 2007-09-14.
- ^ Irena Majerza, Ireneusz Natkaniec (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, Volume 788, Issues 1-3, Pages 93-101 {{doi:10.1016/j.molstruc.2005.11.022}}
- ^ Global Status Report on Alcohol 2004
- ^ Lodgsdon, J.E. (1994). "Ethanol." In J.I. Kroschwitz (Ed.) .^ Kirk-Othmer encyclopedia of chemical technology,; 3rd ed.
- Methanol (EHC 196, 1997) 18 May 2010 14:42 UTC www.inchem.org [Source type: Academic]
^ The Merck index: An encyclopedia of chemicals,; drugs and biologicals, 10th ed.- Methanol (EHC 196, 1997) 18 May 2010 14:42 UTC www.inchem.org [Source type: Academic]
^ Encyclopedia of ; chemical technology, 3rd ed., New York, Wiley Interscience.- Propanol, 2- (EHC 103, 1990) 18 May 2010 14:42 UTC www.inchem.org [Source type: Academic]
9, p. 820. New York: John Wiley & Sons.
- ^ Robert S. Gable (2004). "Comparison of acute lethal toxicity of commonly abused psychoactive substances" (reprint). Addiction 99 (6): 686–696. doi:10.1111/j.1360-0443.2004.00744.x. http://web.cgu.edu/faculty/gabler/toxicity%20Addiction%20offprint.pdf.
- ^ a b Schep LJ, Slaughter RJ, Vale JA, Beasley DM (Sep 30 2009). "A seaman with blindness and confusion". BMJ 339: b3929. doi:10.1136/bmj.b3929. PMID 19793790. http://www.bmj.com/cgi/content/full/339/sep30_1/b3929.
- ^ 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. PMID 19458366.
- ^ Schep LJ, Slaughter RJ, Temple WA, Beasley DM (July 2009). "Diethylene glycol poisoning". Clin Toxicol (Phila) 47 (6): 525–35. doi:10.1080/15563650903086444. ISSN 1556-3650. PMID 19586352.
- ^ Zimmerman HE, Burkhart KK, Donovan JW. Ethylene glycol and methanol poisoning: diagnosis and treatment. Journal of Emergency Nursing. 1999 Apr;25(2):116-20. PMID 10097201
- ^ Lobert S. Ethanol, isopropanol, methanol, and ethylene glycol poisoning. Critical Care Nurse. 2000 December;20(6):41-7. PMID 11878258
- ^ McKee M, Suzcs S, Sárváry A, Adany R, Kiryanov N, Saburova L, Tomkins S, Andreev E, Leon DA. The composition of surrogate alcohols consumed in Russia. Alcoholism, Clinical and Experimental Research. 2005 October;29(10):1884-8. PMID 16269919
- ^ Bunc M, Pezdir T, Mozina H, Mozina M, Brvar M. Butanol ingestion in an airport hangar. Human and Experimental Toxicology. 2006 Apr;25(4):195-7. PMID 16696295
- ^ Woo KL. Determination of low molecular weight alcohols including fusel oil in various samples by diethyl ether extraction and capillary gas chromatography. Journal of AOAC International. 2005 September-October;88(5):1419-27. PMID 16385992
- ^ Lachenmeier DW, Haupt S, Schulz K. Defining maximum levels of higher alcohols in alcoholic beverages and surrogate alcohol products. Regulatory Toxicology and Pharmacology. 2008 Apr;50(3):313-21. PMID 18295386
- ^ Hori H, Fujii W, Hatanaka Y, Suwa Y. Effects of fusel oil on animal hangover models. Alcohol Clinical and Experimental Research. 2003 Aug;27(8 Suppl):37S-41S. PMID 12960505
- ^ Wiernikowski A, Piekoszewski W, Krzyzanowska-Kierepka E, Gomułka E. Acute oral poisoning with isopropyl alcohol in alcoholics. (Polish) Przeglad Lekarski. 1997;54(6):459-63. PMID 9333902
- ^ Mańkowski W, Klimaszyk D, Krupiński B. How to differentiate acute isopropanol poisoning from ethanol intoxication? -- a case report. (Polish) Przeglad Lekarski 2000;57(10):588-90. PMID 11199895
- ^ Bogomolova IN, Bukeshov MK, Bogomolov DV. The forensic medical diagnosis of intoxication of alcohol surrogates by morphological findings. (Russian) Sudebno Meditsinskaia Ekspertiza. 2004 September-October;47(5):22-5. PMID 15523882
Bibliography
- Metcalf, Allan A. (1999). The World in So Many Words. Houghton Mifflin. ISBN 0395959209.
| Alcohols |
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| Primary alcohols (1°) |
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| Secondary alcohols (2°) |
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| Tertiary alcohols (3°) |
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