Paracetamol Presentation

about Paracetamol:

Another name for it is Acetaminophen (APAP)

Very widely used medicine
Used for headaches, arthritis and toothaches
Mild painkiller (Analgesic)
Reduces temperature (Antipyretic),
Ibuprofen is recommended since its more effective
Weak inflammatory
Found in more than 90 common products sold over
counters Vicks and Panadol
Relatively safe drug but with toxic side effects
If doses are more than 10-15g because of the chemical
structure and how it breaks down in our bodies
Its broken down to a very reactive intermediate at high
doses

What does paracetamol do to the body?

It works on a chemical in the body called Prostaglandins

which are released in response to illness/ injuryinflammation
Paracetamol blocks this production by inhibiting
cyclooxygenase (COX) which produces Prostaglandins
makes the body less aware of the pain
Paracetamol is diff from other medications as It blocks this
in the brain and not in the site of the production, which
Aspirin does
Paracetamol Reduces the high BT by acting on the heat
regulatory centre of the brain
Prostaglandins is made in the site where they are needed,
Site of tissue damage and infection , through chemical
reaction

Interesting fact

Paracetamol is extremely toxic to cats as they dont have

the enzymes to break it down safely

Paracetamol is also lethal to snakes, and has been used in
attempts to control the brown tree snake in Guam

Paracetamol with coffee in lethal as it triple the toxic level

in the body and cause liver damage

600 medications with acetaminophen currently approved
for sale in the U.S.
27 billion acetaminophen doses sold in the U.S. in 2009
1,567 Americans who died from 2001-2010 from
accidental acetaminophen poisoning
1,400 Americans who committed suicide by taking
acetaminophen from 2000-2010

What are the chemical reactions in making

paracetamol? (School)
1- Nitration of phenol

Add concentrated sulphuric acid and Sodium nitrate

Produces the nitronium ion
Which attacks the benzene ring of phenol to produce
isomers of nitrophenol
The oh group of phenol activates the benzene ring at 2,4
positions resulting to 2 and 4 nitrophenol production
4 is separated by steam distillation as 2 is more volatile
due to its fewer hydrogen bond with water
Or column chromatography, as 2 is less polar so less
affinity for Silica
2-reduction of nitro group to an amine
Phenols oxygen is strongly activating, The oxygen is lost
from the nitro group of 4th position and H is added to form
4-aminophenol- (Reduction reaction)
3- acetylation of amine with acetic anhydride
4 aminophenol is suspended in water at RTP
Readily reacts with ethanoic anhydride to produce a
precipitate of amide paracetamol

(Industry)
developed by HoechstCelanese
involves direct acylation of phenol with acetic
anhydride catalyzed by HF,
conversion of the ketone to a ketoxime with
hydroxylamine,
followed by the acid-catalyzed Beckmann
rearrangement to give the amide