Ethanol

Ethanol
Full structural formula of ethanol Skeletal formula of ethanol
Ball-and-stick model of ethanol Space-filling model of ethanol
Systematic name

Ethanol[1]

Identifiers
CAS number  YesY
Jmol-3D images Image 1
Properties
Molecular formula C2H6O
Molar mass 46.07 g mol−1
Density 0.789 g/cm3 (at 25°C)
Melting point −114 °C (−173 °F; 159 K)
Boiling point 78.37 °C (173.07 °F; 351.52 K)
Acidity (pKa) 15.9 (H2O), 29.8 (DMSO)[2][3]
Hazards[4]
MSDS External MSDS
R-phrases R11
S-phrases (S2), S7, S16
Flash point 16 °C (61 °F; 289 K)
Autoignition temperature 365 °C (689 °F; 638 K)
LD50 7060 mg/kg (oral, rat)[5]
Related compounds
Related compounds Methanol
Ethane
Supplementary data page
Structure and
properties 		n, εr, etc.
Thermodynamic
data 		Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N   YesY/N?)

Commonly referred to simply as alcohol or spirits, ethanol is also called ethyl alcohol, and drinking alcohol. It is the principal type of alcohol found in alcoholic beverages, produced by the fermentation of sugars by yeasts. It is a neurotoxic[6][7] psychoactive drug and one of the oldest recreational drugs used by humans. It can cause alcohol intoxication when consumed in sufficient quantity. Ethanol is used as a solvent, an antiseptic, a fuel and the active fluid in modern (post-mercury) thermometers. It is a volatile, flammable, colorless liquid with a strong chemical odor. Its structural formula CH
3CH
2OH, is often abbreviated as C
2H
5OH, C
2H
6O or EtOH.

Contents

  • Etymology 1
  • Chemical formula 2
  • Natural occurrence 3
  • Pharmacology 4
    • Activity profile 4.1
    • Properties 4.2
    • Short-term 4.3
      • Effects on the central nervous system 4.3.1
      • Effects on metabolism 4.3.2
      • Drug interactions 4.3.3
      • Alcohol and digestion 4.3.4
      • Alcohol and gastrointestinal diseases 4.3.5
      • Magnitude of effects 4.3.6
    • Long-term 4.4
      • Birth defects 4.4.1
      • Cancer 4.4.2
      • Other effects 4.4.3
  • History 5
  • Properties 6
    • Physical properties 6.1
    • Solvent properties 6.2
    • Flammability 6.3
  • Production 7
    • Ethylene hydration 7.1
    • Fermentation 7.2
      • Cellulose 7.2.1
      • Hydrocarbon 7.2.2
    • Testing 7.3
  • Research 8
  • Purification 9
    • Distillation 9.1
    • Molecular sieves and desiccants 9.2
    • Membranes and reverse osmosis 9.3
    • Other techniques 9.4
  • Grades of ethanol 10
    • Denatured alcohol 10.1
    • Absolute alcohol 10.2
    • Rectified spirits 10.3
  • Reactions 11
    • Ester formation 11.1
    • Dehydration 11.2
    • Combustion 11.3
    • Acid-base chemistry 11.4
    • Halogenation 11.5
    • Oxidation 11.6
  • Other uses 12
    • Motor fuel 12.1
    • Household heating 12.2
    • Feedstock 12.3
    • Antiseptic 12.4
    • Solvent 12.5
  • Charts 13
  • History 14
  • See also 15
  • References 16
  • Further reading 17
  • External links 18

Etymology

Ethanol is 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.[8] Ethyl is a contraction of the French word ether (any substance that evaporated or sublimated readily at room temperature) and the Greek word ύλη (hyle, substance).[9]

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.[10]

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-kuḥl,[11] 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

Ethanol is a 2-carbon alcohol. Its molecular formula is CH3CH2OH. An alternative notation is CH3–CH2–OH, which indicates that the carbon of a methyl group (CH3–) is attached to the carbon of a methylene 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.

Natural occurrence

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.[12] 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.[13] Ethanol is also produced during the germination of many plants as a result of natural anerobiosis.[14] Ethanol has been detected in outer space, forming an icy coating around dust grains in interstellar clouds.[15] Minute quantity amounts (244 ppb) of endogenous ethanol and acetaldehyde were found in the exhaled breath of healthy volunteers.[16]

Pharmacology

Activity profile

Ethanol is known to possess the following direct pharmacodynamic actions (most important actions are bolded):[17]

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.[17]

Properties

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.[21]

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.[22] Ethylene glycol poisoning can be treated in the same way.

Pure ethanol will irritate the skin and eyes.[23] Nausea, vomiting and intoxication are symptoms of ingestion. Long-term use by ingestion can result in serious liver damage.[24] Atmospheric concentrations above one in a thousand are above the European Union Occupational exposure limits.[24]

Short-term

BAC (g/L) BAC
(% v/v) 		Symptoms[25]
0.5 0.05% Euphoria, talkativeness, relaxation
1 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
3 0.3% Stupefaction, possible unconsciousness
4 0.4% Possible death
>5.5 >0.55% Death

Effects on the central nervous system

Ethanol is a central nervous system depressant and has significant psychoactive effects in sublethal doses; for specifics, see "Effects of alcohol on the body by dose". Based on its abilities to change the human consciousness, ethanol is considered a psychoactive drug.[26] Death from ethanol consumption is possible when blood alcohol level reaches 0.4%. A blood level of 0.5% or more is commonly fatal. Levels of even less than 0.1% can cause intoxication, with unconsciousness often occurring at 0.3–0.4%.[27]

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. The table at the right summarizes the symptoms of ethanol consumption. 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 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).[28]

Prolonged heavy consumption of alcohol can cause significant permanent damage to the brain and other organs. See Alcohol consumption and health.

According to the US National Highway Traffic Safety Administration, in 2002 about "41% of people fatally injured in traffic crashes were in alcohol related crashes".[29] The risk of a fatal car accident increases exponentially with the level of alcohol in the driver's blood.[30] Most drunk driving laws governing the acceptable levels in the blood while driving or operating heavy machinery set typical upper limits of blood alcohol content (BAC) between 0.02% and 0.08%.

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.

The reinforcing effects of alcohol consumption are also mediated by acetaldehyde generated by catalase and other oxidizing enzymes such as cytochrome P-4502E1 in the brain.[31] 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.[32]

Effects on metabolism

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.[33] However, the product of the first step of this breakdown, acetaldehyde,[34] 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[35] 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.

Drug interactions

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.[27] It interacts with cocaine in vivo to produce cocaethylene, another psychoactive substance.[36] Ethanol enhances the bioavailability of methylphenidate (elevated plasma d-MPH).[37] In combination with cannabis, ethanol increases plasma THC levels, which suggets that ethanol may increase the absorption of THC.[38]

Alcohol and metronidazole

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.[39] 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.[40][41][41] 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.[42]

Alcohol and digestion

compare
Digestive system

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.[43] 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.[44] 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.[44] This is the underlying principle of the alcohol breath testing (or breathalyzers) to determine if a driver has been drinking and driving.[45]

From the lungs, blood returns to the heart and will be distributed throughout the body. Interestingly, alcohol increases levels of high-density lipoproteins(HDLs), which carry cholesterol.[44] Alcohol is known to make blood less likely to clot, reducing risk of heart attack and stroke. This could be the reason why alcohol could produce health benefits when consumed in moderate amounts.[46] Also, alcohol dilates blood vessels. Consequently, a person will feel warmer, and their face turns flush and pink.[44]

Loss of balance
When alcohol reaches the brain, it has the ability to delay signals that are sent between nerve cells that control balance, thinking and movement.[44]

Frequent urination
Moreover, alcohol can affect the brain's ability to produce antidiuretic hormones. These hormones are responsible for controlling the amount of urine that is produced. Alcohol prevents the body from reabsorbing water, and consequently a person who recently drank alcohol will urinate frequently.[44]

Alcohol and gastrointestinal diseases

compare
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.[47] 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.[48] A person who drinks alcohol regularly is strongly advised to reduce their intake to prevent PUD aggravation.[48]

Magnitude of effects

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.[49]

Long-term

Birth defects

Ethanol is classified as a teratogen. See fetal alcohol syndrome and fetal alcohol spectrum disorder.

Cancer

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.".[50]

Other effects

Frequent drinking of alcoholic beverages has been shown to be a major contributing factor in cases of elevated blood levels of triglycerides.[51]

Ethanol is also widely used, clinically and over the counter, as an antitussive agent.[52]

History

The fermentation of sugar into ethanol is one of the earliest biotechnologies employed by humans. The intoxicating effects of ethanol consumption have been known since ancient times. Ethanol has been used by humans since prehistory as the intoxicating ingredient of alcoholic beverages. Dried residue on 9,000-year-old pottery found in China suggests that Neolithic people consumed alcoholic beverages.[53]

Although distillation was well known by the early Greeks and Arabs, the first recorded production of alcohol from distilled wine was by the School of Salerno alchemists in the 12th century.[54] The first to mention absolute alcohol, in contrast with alcohol-water mixtures, was Raymond Lull.[54]

In 1796, German-Russian chemist Johann Tobias Lowitz obtained pure ethanol by mixing partially purified ethanol (the alcohol-water azeotrope) with an excess of anhydrous alkali and then distilling the mixture over low heat.[55] French chemist Antoine Lavoisier described ethanol as a compound of carbon, hydrogen, and oxygen, and in 1807 Nicolas-Théodore de Saussure determined ethanol's chemical formula.[56][57] Fifty years later, Archibald Scott Couper published the structural formula of ethanol. It was one of the first structural formulas determined.[58]

Ethanol was first prepared synthetically in 1825 by

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  • Alcohol (Ethanol) at The Periodic Table of Videos (University of Nottingham)
  • International Labour Organization ethanol safety information
  • National Pollutant Inventory – Ethanol Fact Sheet
  • CDC – NIOSH Pocket Guide to Chemical Hazards – Ethyl Alcohol
  • National Institute of Standards and Technology chemical data on ethanol
  • ChEBI – biology related
  • Chicago Board of Trade news and market data on ethanol futures
  • Calculation of vapor pressure, liquid density, dynamic liquid viscosity, surface tension of ethanol
  • Ethanol History A look into the history of ethanol
  • ChemSub Online: Ethyl alcohol
  • Industrial ethanol production process flow diagram using ethylene and sulphuric acid

External links

  • The National Institute on Alcohol Abuse and Alcoholism maintains a database of alcohol-related health effects. ETOH Archival Database (1972–2003) Alcohol and Alcohol Problems Science Database.
  • Boyce, John M., and Pittet Didier. (2003). "Hand Hygiene in Healthcare Settings". Georgia, United States.
  • Onuki, Shinnosuke; Koziel, Jacek A.; van Leeuwen, Johannes; Jenks, William S.; Grewell, David; Cai, Lingshuang (June 2008). "Ethanol production, purification, and analysis techniques: a review". 2008 ASABE Annual International Meeting. Providence, RI. Retrieved February 16, 2013. 
  • Sci-toys website explanation of US denatured alcohol designations
  • Smith, M.G., and M. Snyder. (2005). "Ethanol-induced virulence of Acinetobacter baumannii". American Society for Microbiology meeting. Volume 1 June 5 – June 9. Atlanta.

Further reading

  1. ^ a b "Ethanol – Compound Summary". The PubChem Project. USA: National Center for Biotechnology Information. 
  2. ^ Ballinger, P., Long, F.A. (1960). "Acid Ionization Constants of Alcohols. II. Acidities of Some Substituted Methanols and Related Compounds1,2". Journal of the American Chemical Society 82 (4): 795.  
  3. ^ Arnett, E.M., Venkatasubramaniam, K.G. (1983). "Thermochemical acidities in three superbase systems". J. Org. Chem. 48 (10): 1569.  
  4. ^ "Ethanol Material Safety Data Sheet – Europe". Distill.com. Retrieved 2014-01-18. 
  5. ^ "ChemIDplus - 64-17-5 - LFQSCWFLJHTTHZ-UHFFFAOYSA-N - Alcohol [USP] - Similar structures search, synonyms, formulas, resource links, and other chemical information.". Retrieved 13 October 2014. 
  6. ^
  7. ^ Brust, John C.M. (4 April 2010). "Ethanol and Cognition: Indirect Effects, Neurotoxicity and Neuroprotection: A Review". International Journal of Environmental Research and Public Health. Int. J. Environ. Res. Public Health. pp. 1540–1557.  
  8. ^ Liebig, Justus (1834) "Ueber die Constitution des Aethers und seiner Verbindungen" (On the constitution of ether and its compounds), Annalen der Pharmacie, 9 : 1–39. From page 18: "Bezeichnen wir die Kohlenwasserstoffverbindung 4C + 10H als das Radikal des Aethers mit E2 und nennen es Ethyl, …" (Let us designate the hydrocarbon compound 4C + 10H as the radical of ether with E2 and name it ethyl …).
  9. ^  
  10. ^ For a report on the 1892 International Conference on Chemical Nomenclature, see:
    • Armstrong, Henry (1892). "The International Conference on Chemical Nomenclature". Nature 46 (1177): 56–59.  
    • Armstrong's report is reprinted with the resolutions in English in: Armstrong, Henry (1892). "The International Conference on Chemical Nomenclature". The Journal of Analytical and Applied Chemistry 6: 390–400 (398). The alcohols and the phenols will be called after the name of the hydrocarbon from which they are derived, terminated with the suffix ol (ex. pentanol, pentenol, etc.). 
  11. ^ OED; etymonline.com
  12. ^ Dudley, Robert (2004). "Ethanol, Fruit Ripening, and the Historical Origins of Human Alcoholism in Primate Frugivory". Integrative Comparative Biology 44 (4): 315–323.  
  13. ^ Graber, Cynthia (2008). "Fact or Fiction?: Animals Like to Get Drunk". Scientific American. Retrieved 2010-07-23. 
  14. ^ Leblová, Sylva; Sinecká, Eva and Vaníčková, Věra (1974). "Pyruvate metabolism in germinating seeds during natural anaerobiosis". Biologia Plantarum 16 (6): 406–411.  
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  23. ^ Minutes of Meeting. Technical Committee on Classification and Properties of Hazardous Chemical Data (January 12–13, 2010).
  24. ^ a b "Safety data for ethyl alcohol". Msds.chem.ox.ac.uk. 2008-05-09. Retrieved 2011-01-03. 
  25. ^ Pohorecky LA, Brick J (1988). "Pharmacology of ethanol". Pharmacol. Ther 36 (2–3): 335–427.  
  26. ^ Alcohol use and safe drinking. US National Institutes of Health .
  27. ^ a b Yost, David A. (2002). "Acute care for alcohol intoxication" 112 (6). Postgraduate Medicine Online. Archived from the original on 2010-12-14. Retrieved 2007-09-29. 
  28. ^
  29. ^ Hingson R, Winter M (2003). "Epidemiology and consequences of drinking and driving". Alcohol research & health : the journal of the National Institute on Alcohol Abuse and Alcoholism 27 (1): 63–78.  
  30. ^ Naranjo CA, Bremner KE (1993). "Behavioural correlates of alcohol intoxication".  
  31. ^ Karahanian, E.; Quintanilla, M. A. E.; Tampier, L.; Rivera-Meza, M.; Bustamante, D.; Gonzalez-Lira, V. C.; Morales, P.; Herrera-Marschitz, M.; Israel, Y. (2011). "Ethanol as a Prodrug: Brain Metabolism of Ethanol Mediates its Reinforcing Effects". Alcoholism: Clinical and Experimental Research 35 (4): 606–612.  
  32. ^ Melis, M.; Enrico, P.; Peana, A. T.; Diana, M. (2007). "Acetaldehyde mediates alcohol activation of the mesolimbic dopamine system". European Journal of Neuroscience 26 (10): 2824–2833.  
  33. ^ Nutrition Coordinating Center, University of Minnesota. "Primary Energy Sources". Regents of the University of Minnesota. Retrieved July 15, 2014. 
  34. ^ Boggan, Bill. "Metabolism of Ethyl Alcohol in the Body". Chemases.com. Retrieved 2007-09-29. 
  35. ^ Boggan, Bill. "Effects of Ethyl Alcohol on Organ Function". Chemases.com. Retrieved 2007-09-29. 
  36. ^ Laizure, S. C.; Mandrell, T.; Gades, N. M.; Parker, R. B. (2003). "Cocaethylene metabolism and interaction with cocaine and ethanol: Role of carboxylesterases". Drug metabolism and disposition: the biological fate of chemicals 31 (1): 16–20.  
  37. ^ Sakalo, V. S.; Romanenko, A. M.; Klimenko, I. A.; Persidskiĭ, IuV (1988). "Effects of chemotherapy on regional metastases of non-seminomatous tumors of the testis". Voprosy onkologii 34 (10): 1219–24.  
  38. ^ Lukas, Scott E.; Orozco, Sara (2001). "Ethanol increases plasma Δ9-tetrahydrocannabinol (THC) levels and subjective effects after marihuana smoking in human volunteers". Drug and Alcohol Dependence 64 (2): 143–9.  
  39. ^ Repchinsky C (ed.) (2012). Compendium of pharmaceuticals and specialties, Ottawa: Canadian Pharmacists Association.
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  42. ^ "Ethanol/metronidazole", p. 335 in Tatro DS, Olin BR, eds. Drug interaction facts. St. Louis: JB Lippincott Co, 1988, ISBN 0932686478.
  43. ^ Sherwood, Lauralee; Kell, Robert and Ward, Christopher (2010). Human Physiology: From Cells to Systems. Cengage Learning.  
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  45. ^ How Breathalyzers work. Electronics.howstuffworks.com
  46. ^ "Alcohol effects on the digestive system". Alcoholrehab.com
  47. ^ Overview of Peptic Ulcer Disease: Etiology and Pathophysiology. Medscape.com. Retrieved on 2013-04-27.
  48. ^ a b Peptic Ulcer Disease (Stomach Ulcers) Cause, Symptoms, Treatments. Webmd.com. Retrieved on 2013-04-27.
  49. ^ Agarwal DP, Goedde HW (1992). "Pharmacogenetics of alcohol metabolism and alcoholism". Pharmacogenetics 2 (2): 48–62.  
  50. ^ http://monographs.iarc.fr/ENG/Classification/ClassificationsGroupOrder.pdf
  51. ^ "Triglycerides". American Heart Association. Archived from the original on 2007-08-27. Retrieved 2007-09-04. 
  52. ^ Calesnick, B.; Vernick, H. (1971). "Antitussive activity of ethanol". Q J Stud Alcohol 32 (2): 434–441.  
  53. ^ Roach, J. (July 18, 2005). "9,000-Year-Old Beer Re-Created From Chinese Recipe". National Geographic News. Retrieved 2007-09-03. 
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