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Acetaminophen (Paracetamol, APAP), is an over the counter pain reliever that also reduces fever. It is commonly used to reduce pain associated with headaches, migraines, back ache, cold, and flu. Overuse of acetaminophen causes serious liver damage. Its general mechanism of action is inhibition of the COX-2 enzyme.


[top]Introduction to Acetaminophen

[top]Using Acetaminophen

[top]Ways of administration

Oral, rectal

[top]Effects of Acetaminophen

[top]Combinations with Acetaminophen

Acetaminophen is both an effective antipyretic (fever reducer) and analgesic (pain reliever). As such, it is found in combination with many other medications. It is important to note that acetaminophen is frequently referred to by other names. Other terms for acetaminophen are APAP (short for acetyl-para-aminophenol) and paracetamol in the UK and other countries. If the ingredient list contains either of these terms, the medication contains acetaminophen.

Common examples of other medications containing acetaminophen are certain cough syrups and prescription painkillers. Percocet and Vicodin are perhaps the most well-known combination medications, the former containing oxycodone and acetaminophen and the latter containing hydrocodone and acetaminophen.

[top]Different Uses for Acetaminophen

[top]Pharmacology of Acetaminophen

LD50 (mg/kg) [1]:
Mice : 338 orally, 500 intraperitoneally

[top]Chemistry of Acetaminophen

Systematic (IUPAC) name:N-(4-hydroxyphenyl)ethanamide
Synonyms:N-(4-hydroxyphenyl)acetamide, 4'-hydroxyacetanilide, p-acetamidophenol, p-acetaminophenol, p-acetylamidophenol, N-acetyl-p-aminophenol, paracetamol, Acamol, Alpiny, Alvedon, Anhiba, Benu-ron, Calpol, Calradol, Captin, Dafalgam, Datril, Dirox, Disprol, Doliprane, Dolitabs, Dolviran, Efferalgan, Efferalganodis, Enelfa, Expandox, Fensum, Geluprane, Hedex, Malex, Mejoralito, Panadol, Panamax, Panodil, Pasolind N, Perfalcan, Sanipirina, Sedalito, Tempra, Tylenol
Molecular Formula:C8H9NO2
Molar mass:151.16 g/mol [2]
CAS Registry Number:103-90-2
Melting Point:169-170.5C
Boiling Point:no data
Flash Point:no data
Solubility:see next section; soluble in 1M NaOH
Additionnal data:density 1.293 (21C)
Notes:Aspect : large monoclinic prisms; crystallized from water

[top]Physical properties of Acetaminophen

Solubility of acetaminophen in different solvents at several temperatures, given in grams of acetaminophen per kg of solvent:

solvent at -5C at 0C at 5C at 10C at 15C at 20 C at 25C at 30C
water 7.21 8.21 9.44 10.97 12.78 14.9 17.39
methanol 174.48 191.48 215.09 239.6 265.43 297.81 332.11 371.61
ethanol 118.56 129.65 141.82 156.14 171.4 190.61 209.91 232.75
1,2-ethanediol 144.3
1-propanol 65.88 72.3 79.62 88.22 96.77 108.09 119.32 132.77
2-propanol 64.41 71.19 79.02 87.67 97.38 108.78 121.15 135.01
1-butanol 47.55 51.96 57.21 63.31 69.29 77.07 83.27 93.64
1-pentanol 67.82
1-hexanol 49.71
1-heptanol 37.43
1-octanol 27.47
acetone 50.39 55.61 62.32 69.63 78.48 88.09 99.83 111.65
2-butanone 69.99
4-methyl-2-pentanone 17.81
tetrahydrofuran 155.37
1,4-dioxane 17.08
ethyl acetate 4.46 5.27 5.78 6.42 7.37 8.52 9.45 10.73
acetonitrile 9.44 11.18 13.44 15.98 19.34 23.1 27.54 32.83
diethylamine 1316.9
N,N-dimethylformamide 1012.02
dimethyl sulfoxide 1132.56
acetic acid 82.72
dichloromethane 0.32
chloroform 1.54
carbon tetrachloride 0.89
toluene 0.22 0.27 0.32 0.36 0.37 0.37 0.34

[top]The dangers of Acetaminophen

Acetaminophen when used in combination with alcohol is known to cause severe liver damage.

High doses of acetaminophen are also associated with liver damage.

The maximum amount of acetaminophen to be taken in one dose should not exceed 1,000mg. The maximum amount of acetaminophen to be taken in 24 hours should not exceed 4,000mg. Recently, the FDA lowered the maximum recommended daily dose to 3,000mg in order to combat acetaminophen overdoses taken by various medications containing the ingredient. Single doses should be separated by 4-6 hours.

Single doses or daily amounts over these amounts can lead to severe liver damage or even failure. If you or someone you know has taken an overdose of acetaminophen, prompt medical attention is necessary. Treatment for such overdoses must be given early, and the apparent effects of liver damage or failure may not be present for 24-72 hours. Liver damage/failure can be completely asymptomatic in the early stages.

[top]Producing Acetaminophen

[top]Forms of Acetaminophen

[top]Legal status of Acetaminophen

[top]United Nations

Not scheduled


Unrestricted. OTC



Unscheduled (may be sold at any registered retail business) in preparations containing less than 30 units per package.
Schedule 2 drug (only available at pharmacies) for paracetamol products containing more than 30 units per package.

[top]Other Countries

[top]History of Acetaminophen

[top]More Acetaminophen Sections


[1]Merck Index, fifteenth edition (2013)
[2]Calculated from Atomic Weights of the Elements, 2007

Created by NeuroChi, 13-02-2011 at 01:49
Last edited by NorthQueensland, 24-11-2015 at 06:59
Last comment by baZING on 02-07-2012 at 19:31
5 Comments, 120,617 Views

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