CHEMISTRY INVESTIGATORY PROJECT:

CHEMISTRY INVESTIGATORY PROJECT - Shashank Shekhar

ASPIRIN:
ASPIRIN

WHAT IS IT???:
WHAT IS IT??? Aspirin also known as acetylsalicylic acid , is a salicylate drug, often used as an analgesic to relieve minor aches and pains, as an antipyretic to reduce fever, and as an antiinflammatory medication. Salicylic acid, the main metabolite of aspirin, is an integral part of human and animal metabolism. While much of it is attributable to diet, a substantial part is synthesized endogenously.

WHAT IS IT???:
WHAT IS IT??? Aspirin also has an antiplatelet effect by inhibiting the production of thromboxane , which under normal circumstances binds platelet molecules together to create a patch over damaged walls of blood vessels. Because the platelet patch can become too large and also block blood flow, locally and downstream, aspirin is also used long-term, at low doses, to help prevent heart attacks, strokes, and blood clot formation in people at high risk of developing blood clots.

WHAT IS IT???:
WHAT IS IT??? Today, aspirin is one of the most widely used medications in the world, with an estimated 40,000 tones of it being consumed each year. In countries where Aspirin is a registered trademark owned by Bayer, the generic term is acetylsalicylic acid (ASA).

Medical uses :
Medical uses

Slide 7:
Aspirin is used for the treatment of a number of conditions including: fever, pain, rheumatic fever, inflammatory diseases such as rheumatoid arthritis, pericarditis , and Kawasaki disease. It

is used in the prevention of transient ischemic attacks, strokes, heart attacks, pregnancy loss, and cancer.

Few examples in Medical uses:

Few examples in Medical uses

PAIN:
PAIN In general, aspirin works well for dull, throbbing pain; it is ineffective for pain caused by most muscle cramps, bloating, gastric distension, and acute skin irritation. The most studied example is pain after surgery, such as tooth extraction, for which the highest allowed dose of aspirin (1 g) is equivalent to 1 g of paracetamol , 60 mg of codeine, or 5 mg of oxycodone

PAIN:
PAIN A combination of aspirin and caffeine, in general, affords greater pain relief than aspirin alone. Effervescent aspirin alleviates pain much faster than aspirin in tablets (1530 min vs. 45 60 min).

HEADACHE:
HEADACHE Aspirin is a first-line drug in the treatment of migraine, bringing relief in 5060% of the cases. When used at a high dose of 1000 mg, no significant differences were seen as compared to triptan medication, sumatriptan and other painkillers such as paracetamol or ibuprofen.

HEADACHE:
HEADACHE The combination of aspirin, paracetamol (acetaminophen) and caffeine (as found in the OTC brand Excedrin) is even more potent. For the treatment of migraine headache, this formulation works better than any of its three components taken separately, better than ibuprofen and better than sumatriptan Similarly to all other medications for migraine, it is recommended to take aspirin at the first signs of the headache, and it is the way these medications were used in the comparative clinical trials.

Prevention of heart attacks and strokes :

Prevention of heart attacks and strokes There are two distinct uses of aspirin for prophylaxis of cardiovascular events: primary prevention and secondary prevention. Primary prevention is

about decreasing strokes and heart attacks in the general population of those who have no diagnosed heart or vascular problems. Secondary prevention concerns patients with known cardiovascular disease.

Prevention of heart attacks and strokes :

Prevention of heart attacks and strokes Low doses of aspirin are recommended for the secondary prevention of strokes and heart attacks. For both males and females diagnosed with cardiovascular disease, aspirin reduces the chance of a heart attack and ischaemic stroke by about a fifth.

Prevention of heart attacks and strokes :

Prevention of heart attacks and strokes This translates to an absolute rate reduction from 8.2% to 6.7% of such events per year for people already with cardiovascular disease. Although aspirin also raises the risk of hemorrhagic stroke and other major bleeds by about twofold, these events are rare, and the balance of aspirin's effects is positive. Thus, in secondary prevention trials, aspirin reduced the overall mortality by about a tenth.

Adverse effects :
Adverse effects

Contraindications :
Contraindications Aspirin should not be taken by people who are allergic to ibuprofen or naproxen, or who have salicylate intolerance or a more generalized drug intolerance to NSAIDs, and caution should be exercised in those with asthma or NSAIDprecipitated bronchospasm

Contraindications :
Contraindications Owing to its effect on the stomach lining, manufacturers recommend people with peptic ulcers, mild diabetes, or gastritis seek medical advice before using aspirin. Even if none of these conditions is present, there is still an increased risk of stomach bleeding when aspirin is taken with alcohol . Patients with hemophilia or other bleeding tendencies should not take aspirin or other salicylates .

Gastrointestinal :

Gastrointestinal Aspirin use has been shown to increase the risk of gastrointestinal bleeding.

Gastrointestinal :
Gastrointestinal Although some enteric coated formulations of aspirin are advertised as being "gentle to the stomach", in one study enteric coating did not seem to reduce this risk. Combining aspirin with other NSAIDs has also been shown to further increase this risk. Using aspirin in combination with clopidogrel or warfarin also increases the risk of upper gastrointestinal bleeding.

Gastrointestinal :
Gastrointestinal In addition to enteric coating, "buffering" is the other main method companies have used to try to mitigate the problem of gastrointestinal bleeding. Buffering agents are intended to work by preventing the aspirin from concentrating in the walls of the stomach, although the benefits of buffered aspirin are disputed. Almost any buffering agent used in antacids can be used; Bufferin , for example, uses MgO . Other preparations use CaCO 3 .

Central effects :
Central effects Large doses of salicylate , a metabolite of aspirin, have been proposed to cause tinnitus (ringing in the ears) based on experiments in rats, via the action on arachidonic acid and NMDA receptors cascade.

Hives and swelling :

Hives and swelling For a small number of people, taking aspirin can result in symptoms that resemble an allergic reaction, including hives, swelling and headache. The reaction is caused by salicylate intolerance and is not a true allergy, but rather an inability to metabolize even small amounts of aspirin, resulting in an overdose.

HOW TO PREPARE ASPIRIN???:

HOW TO PREPARE ASPIRIN??? Materials 3.0 g salicylic acid 6 mL acetic anhydride* 5-8 drops of 85% phosphoric acid or concentrated sulfuric acid* distilled water (about 50 mL ) 10 mL ethanol 1% iron III chloride (optional, to test purity)

Equipments:

Equipments filter paper (12.5 cm) ring stand with funnel two 400 mL beakers 125 mL Erlenmeyer flask 50 mL buret or measuring pipet 10 mL and 50 mL graduated cylinder fume hood, hot plate, balance dropper stirring rod ice bath wash bottle

Procedure :
Procedure Accurately weigh 3.00 grams of salicylic acid and transfer to a dry Erlenmeyer flask. If you will be calculating actual and theoretical yield , be sure to record how much salicylic acid you actually measured. Add 6 mL of acetic anhydride and 5-8 drops of 85% phosphoric acid to the flask. Gently swirl the flask to mix the solution. Place the flask in a beaker of warm water for ~15 minutes.

Slide 27:
Add 20 drops of cold water dropwise to the warm solution to destroy the excess acetic anhydride. Add 20 mL of water to the flask. Set the flask in an ice bath to cool the mixture and speed crystallization. When the crystallization process appears complete, pour the mixture through a Buckner funnel. Apply suction filtration through the funnel and wash the crystals with a few milliliters of ice cold water. Be sure the water is near freezing to minimize loss of product.

Slide 28:
Perform a recrystallization to purify the product. Transfer the crystals to a beaker. Add 10 mL of ethanol. Stir and warm the beaker to dissolve the crystals. After the crystals have dissolved, add 25 mL of warm water to the alcohol solution. Cover the beaker. Crystals will reform as the solution cools. Once crystallization has started, set the beaker in an ice bath to complete the recrystallization .

Slide 29:
Pour the contents of the beaker into a Buckner funnel and apply suction filtration. Remove the crystals to dry paper to remove excess water. Confirm you have acetylsalicylic acid by verifying a melting point of 135C.

Thank you :
Thank you