Aspro, Aspirin, and World War I

2015, a very significant year for all Australians and New Zealanders, marks the centenary of the "Landing at Gallipoli" on 25^th April 1914 and the birth of the ANZAC legend. It also marks the centenary of "Aspro" and the birth of a giant international pharmaceutical company that began in Australia as a direct result of World War I.

Felix Hoffman, a German Chemist, first synthesized aspirin, acetylsalicylic acid (2-Ethanoyloxybenzene carboxylic acid), in 1897 while working for the German pharmaceutical company Bayer AG. This was the first major product released by Bayer AG and the trademark Aspirin was registered worldwide. Prior to 1914 Germany exported Aspirin all over the world.

German supplies of Aspirin to Australia (and other countries) were cut off with the outbreak of World War I in 1914, prompting the then Attorney-General W. M. Hughes (and the 7^th Australian Prime Minister from 1915 to 1923) to suspend German patents and trademarks and grant them to any Australian-based manufacturer who could meet the requirements for purity and safety.

George Richard Rich Nicholas, a pharmacist who had opened a pharmacy in Punt Road, Windsor in Victoria in 1912, set out to make acetylsalicylic acid. Using kitchen utensils, he measured out quantities of the white salicylic acid powder and the acrid smelling acetic anhydride liquid and reacted them in kerosene tins. Needless to say, although he succeeded in producing acetylsalicylic acid it was impure! With the help of Henry Woolf Shmith, an entrepreneur, the experiments continued until they had pure samples of acetylsalicylic acid. In 1915 their product was tested by the government analyst and found to comply with the requirements of the British Pharmacopoeia so Shmith, Nicholas & Co. were granted a licence to make and sell aspirin in Australia.

Their acetylsalicylic acid product was originally marketed as Nicholas-Aspirin, but George was concerned that the name Aspirin could be reclaimed by Bayer after the war, so, in 1917 the name Aspro was registered.

After the war, in 1921, the name of the company  making Aspro was changed to Nicholas Pty Ltd and moved from Windsor to South Melbourne. In 1923, New Zealand began production of Aspro. Between 1925 and 1927 sales of Aspro were expanding in Europe and Asia. In 1927,  George's brother Alfred set up the company Aspro Ltd in England, which became a public company in 1935. In 1969 Nicholas Australia Ltd bought out the English Aspro-Nicholas Ltd, which, in 1970, became Nicholas International Ltd. In 1981 Nicholas International Ltd merged with Kiwi International Ltd (makers of the famous Kiwi shoe polish) to form the Australian public company Nicholas Kiwi. In 1984 Sara Lee acquired Nicholas Kiwi, and in 1988 Piramal India acquired Nicholas Laboratories from Sara Lee.

Ready to learn about the chemistry of aspirin and aspro?
Go to the Free Chemistry Tutorial on Aspirin at AUS-e-TUTE to read about the reactions that produced aspirin as well as the physical and chemical properties of aspirin.
(AUS-e-TUTE Members should log-in to the Test Centre and use the "Members ONLY" Aspirin Tutorial).
AUS-e-TUTE members also have access to other learning resources, such as games, tests and exams on the chemistry of aspirin.
Find out about AUS-e-TUTE membership here.
And you can become an AUS-e-TUTE member here, and start improving your chemistry results today!

Salts of Drugs a Health Risk

Many studies have shown that excess salt is harmful to heart health, but many commonly prescribed medicines have sodium added to improve their absorption into the body, but the effect of doing this has not been known. For example, 1 Alka-Seltzer tablet contains 324 mg of aspirin (the drug) and 445 mg of sodium.
University of Dundee and College of London researchers have found that a person taking the maximum, daily dose of some medicines would exceed the recommended daily dietary intake limits for sodium. In Australia, the total maximum recommended limit of sodium for adults should be less than 2300 mg per day (less for children). The label on the Alka-Seltzer tablets carries a warning that you should not take more than 8 tablets per day.
In the study, the researchers found that patients taking the sodium-containing medication had a 16% increased risk of a heart attack, were 7 times more likely to develop high blood pressure, and, were 28% more likely to die, compared with patients who took the non-sodium containing versions of the same drug.

So why do we add sodium to drugs if it is potentially harmful?

We do this because many drugs are actually insoluble in water. The cells in your body are made up mostly of water, so if you want to be able to transport a drug around the body, and have it absorbed into cells, it is beneficial if the drug is soluble in water.

How do we add sodium to drugs?

If the drug is, for example, a weak acid like aspirin, then it is not very soluble in water.
Being a weak acid, though, aspirin can undergo a proton transfer (neutralisation) reaction with a base such as sodium hydroxide. The product of a neutralisation reaction are salt and water.
acid + base → salt + water

aspirin + sodium hydroxide → sodium salt of aspirin + water

The sodium salt of aspirin readily dissolves in water by dissociating into positive sodium ions and negative "aspirin" ions.


Reference:
BMJ-British Medical Journal (2013, November 26). High salt levels in medicines increase risk of cardiovascular events. ScienceDaily. Retrieved November 28, 2013, from http://www.sciencedaily.com­ /releases/2013/11/131126191557.htm 

Further Reading
aspirin
mass conversions 
ppm
molarity
neutralisation
proton transfer reactions
acid dissociation constants

Suggested Study Questions: 

1. Convert these masses in milligrams to masses in grams
• 324 mg
• 445 mg
2. The label on the Alka-Seltzer packet recommends dissolving 2 tablets in water. For these two tablets, calculate the mass in milligrams of
• aspirin
• sodium
3. If you were to take the maximum number of tablets, 8, in a day, how much of each of the following substances would you be ingesting?
• aspirin
• sodium
4. Would you be exceeding the recommended daily dietary intake limits for sodium in Australia? Explain your answer.
5. A low salt food is one that contains less than 120 mg of sodium per 100 g of food. If Alka-Seltzer were to be considered a low salt food, what would the mass of each tablet need to be?
6. Aspirin has the molecular formula C₉H₈O₄. What is the molar mass of aspirin?
7. The sodium salt of aspirin has the molecular formula C₉H₇O₄^-Na⁺. What is the molar mass of the sodium salt of aspirin?
8. Calculate the mass of sodium in 1 Alka-Seltzer tablet due to the sodium salt of aspirin.
9. Compare the mass of sodium calculated above to the actual mass of sodium present in 1 Alka-Seltzer tablet according to the package. How would you explain the difference in the two masses?
10. If a person dissolved 2 Akla-Seltzer tablets in 150 mL of water, what is the concentration of sodium ions in the water in
    • mol/L
    • mg/L
    • ppm
11. Recommendations for the daily intake of potassium are higher than those for sodium at 4700 mg day, so one way to alleviate the sodium problem in aspirin tablets might be to replace the sodium with potassium. Describe one way that you could produce the potassium salt of aspirin.