Article Covered
Our article for this project was Warning Against Using Pharma Choice
Acetaminophen with Caffeine and Codeine Caplets, Lot Number lC484 and was
found on the Washington Post Newspaper website under the health heading
in
the "recalls and alerts" section.
Editorial Notes
In August of 2001, the Therapeutic Products Directorate of Health
Canada issued a drug alert concerning Pharma Choice Acetaminophen
with Caffeine and Codeine Caplets, Lot number 1C484. These bottles
accidentally contained round tablets instead of the expected oval
caplets. The tablets had aspirin in them, which could result in
harmful side effects for consumers. Some unwanted side effects
include serious bleeding, stomach ulcers, allergic reactions, and
complications during pregnancy due to the enhanced effects of
aspirin by combination of drug interactions in the body.
Background information on each of the ingredient drugs
Acetaminophen, Caffeine, Codeine, and Aspirin can be found by
clicking on the names. The first three links will take you to the
www.chemfinder.com search page. By typing in the name of the
respective compound, you will be provided with its chemical
information. These links include information on the chemical
structure, Molecular formula, and molecular weight of the
compounds. Further information dealing with the pharmacology of
the separate drugs can be found by clicking on the following
links: Acetaminophen, Caffeine, Codeine, and Aspirin. Since
aspirin was the contaminant, the focus was on studying its
chemistry while only general information is given on the other
drugs.
Further information regarding the synthesis of Aspirin can be
here.
Questions and Answers
Q1. From reading the article you can find that aspirin was the
contaminating
substance in the tablets. Based on the editorial notes and the article
synopsis, deduce the structure of aspirin.
A1.
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Q2. How is aspirin synthesized from the starting materials Phenol, sodium
Hydroxide, Carbon Dioxide, Acetic Anhydride, and Hydrogen.
A2.
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Q3. Name two of the four of these reactions used to synthesize aspirin
from
those reactants.
A3.
1. Nucleophilic substitution
2. Kolbe-Schmitt Reaction step 1 p.952 ch.24
3.Kolbe-schmitt Reaction step 2 p.952 ch.24
4.acetylation of the phenolic hydroxyl group p.952 ch.24
Q4. Based on the chemical name, the molecular formula, and molecular
weight
for acetaminophen given in the editorial notes, determine the structural
formula of this compound.
A4.
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Q5. Based on the chemical name, the molecular formula, and molecular
weight
for caffeine given in the editorial notes, determine the structural
formula
of this compound.
A5.
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Challenge. The chemical name for Codeine is "7,8-didehydro-4,5oe
epoxy-3-methoxy-17~methylmorphinan~6oe-ol phosphate (1:1) hemihydrate.
The
molecular weight and molecular formula is 406.37 and
C18H21NO3*H3PO4*1/2H2O,
respectively. Based on these criteria, can you determine the structure of
Codeine?
Challenge Answer.
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