Noah Gray – Chemistry 11, Block A Ibuprofen Noah Gray – Chemistry 11, Block A

Structural diagram of ibuprofen If you’d like to see a 3D model that you can rotate go to https://pubchem.ncbi.nlm.nih.gov/compound/ibuprofen#section=3D-Conformer http://scienceline.ucsb.edu/getkey.php?key=2503 https://commons.wikimedia.org/wiki/File:(R)-Ibuprofen.svg

Ibuprofens history Ibuprofen was first developed in the early 1960’s Boots Laboratories(British drug manufacturer). Boots realized that Carboxylic Acid was what gave aspirin its anti- inflammatory qualities. The Boots laboratories found a Carboxylic acid with twice the strength as aspirin, and so they tested and made more than 600 compounds with it. Most were ineffective, but the one found most effective was Ibuprofen. It wasn’t until 1974 when Ibuprofen arrived in the United States. It was then that a large company called Whitehall Laboratories Division came out with their Ibuprofen, and they called it Advil. It was in 1983 where it became legal to buy Ibuprofen without a subscription. http://www.rsc.org/learn-chemistry/resources/chemistry-in-your-cupboard/nurofen/7 http://www.discoveriesinmedicine.com/Hu-Mor/Ibuprofen.html

How is Ibuprofen synthesized? There is two common ways to make ibuprofen: The Boot process and the Hoechst process (They are both shown in the image to the right). They both use isobutyl benzene and Friedel-Crafts acylation. The Boot process was the original way to make Ibuprofen but the Hoechst process is a newer process that requires fewer steps. http://www.chm.bris.ac.uk/motm/ibuprofen/synthesis.htm

Properties of Ibuprofen The following are properties of Ibuprofen: Molecular Formula: C₁₃H₁₈O₂ Its appearance is generally white, in the form of powder or tablets. Its predicted melting point is 76 degrees Celsius According to Chemspider.com, Ibuprofen is “stable, combustible, and incompatible with strong oxidizing agents.” Its Average mass is 206.281 Da (Daltons) http://www.chemspider.com/Chemical-Structure.3544.html http://www.drugs.com/ibuprofen.html

Ibuprofens Uses in Society http://www.samsclub.com/sams/advil-tablets-360-ct/prod3110007.ip Ibuprofens main uses are to reduce pain, fever, and inflammation, while as it is most commonly used for menstrual periods, migraines, and arthritis. Ibuprofen is most commonly sold as Advil, but is also widely known by these brands: Brufen, Nurofen, Motrin, and many more. Ibuprofen is often confused with acetaminophen. While they both help relieve pain and fever, acetaminophen does not reduce inflammation. On the other hand, Ibuprofen is tough on the stomach and has fewer side effects. Ibuprofen can be used without a subscription, although the dose is toned down considerably compared to prescription Ibuprofen. There are many different derivatives of Ibuprofen, and the reason for creating derivitives of Ibuprofen is to reduce the amount of gastro toxicity as a side effect.

Problems with Ibuprofen There are multiple side effects from taking Ibuprofen including, but not limited to, nausea, constipation, diarrhea, gastrointestinal bleeding, headache, rash, and hypertension. Taking alcohol with Ibuprofen has been found to increase the risk of stomach bleeding. It is also found that taking high daily doses Ibuprofen may result in cardiovascular risk such as a heart attack or hypertension. Overdosing on Ibuprofen usually does not result in death but a large portion of the symptoms and side effects listed above may occur.

Bibliography https://pubchem.ncbi.nlm.nih.gov/compound/ibuprofen#section=Top http://www.encyclopedia.com/topic/ibuprofen.aspx http://www.discoveriesinmedicine.com/Hu-Mor/Ibuprofen.html http://www.chm.bris.ac.uk/motm/ibuprofen/synthesis.htm http://www.drugbank.ca/drugs/DB01050 https://en.wikipedia.org/wiki/Ibuprofen http://www.chemspider.com/Chemical-Structure.3544.html