acetaminophen

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the wonderful world of Organic Workshop
Semester 2 Jones
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When is a pain reliever not a pain reliever???
As useful as they are, over-the-counter pain
relief medications are a frequent source of
accidental poisoning (see, for example, The New
England Journal of Medicine 1997, 1112). In an
emergency situation, the ability to quickly
identify an unknown toxin is clearly
advantageous. Recently, NMR has shown promise
for the clinical determination of drugs and drug
metabolites, particularly the more common pain
relief medications (see Journal of Analytical
Toxicology 2000, 180). Now youre the hospital
toxicologist charged with the task of identifying
unknown compounds isolated from an unconscious
patient. Shown below are the structures for
three non-steroidal anti-inflammatory drugs
(NSAIDs). Match each structure to the correct
spectra on the following pages (A, B, and C)
save our patient!
?
?
TylenolTM
?
AspirinTM
acetylsalicylic acid
ketoprofen
?
OrudisTM
acetaminophen
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A
13C NMR
1H NMR
IR
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B
13C NMR
1H NMR
IR
4
C
13C NMR
1H NMR
IR