ORGMED LAB: synthesis of acetylsalicylic acid

Aspirin (acetylsalicylic acid) is a _______________ substance.

white, crystalline solid

Aspirin is usually odorless, but develops a __________________ (odor) when exposed to moisture due to hydrolysis into __________________

vinegar-like odor of acetic acid
salicylic and acetic acid

Acetylsalicylic acid has a melting point of:

________°C
________°F

136
277

________________ is known to be one as one of the most common a nonsteroidal anti-inflammatory drug (NSAID) used to reduce pain, fever, and inflammation, and as an antithrombotic.

acetylsalicylic acid

acetylsalicylic acid can also be given (BEFORE / AFTER) taking _________, an anti-tubercular drug to prevent flushing reactions.

isoniazid

name this structure

acetylsalicylic acid

In aspirin, it is believed that the primary mechanism of action is the _____________ which results in the inability to synthesize prostaglandins, prostacyclins, and thromboxane.

irreversible acetylation of cyclooxygenase

as a result of the mechanism of action of aspirin, the pyrogenic effect of prostaglandins on the centers of thermoregulation and sensitive nerve endings is (INCREASED / REDUCED), which leads to a (ENHANCING / LESSENING) of sensitivity to painful neurotransmission

reduced
lessening

The antiaggregatory effect of aspirin is explained by the irreversible inability to synthesize __________ in the thrombocytes.

thromboxane A2

Aspirin can cause:

____________ reactions
_____toxicity
__________ stools
________, _______
and most commonly: ____________

hypersensitivity
ototoxicity
bloody or tar-like stools
rashes, fever
stomach ulcers

Gastric irritation due to aspirin can be caused by (HIGH / LOW) doses of aspirin

high

Gastric irritation due to aspirin can be caused by (HIGH / LOW) doses of aspirin

Gastric irritation due to aspirin can be caused by (CONCOMITANT / SEQUENTIAL) use with other drugs like other NSAIDs, corticosteroids and anticoagulants like ticagrelor, prasugrel, and clopidogrel

concomitant (sabay)

Gastric irritation due to aspirin can be caused by triple antithrombotic therapy of the drugs: _______, ________, ________

aspirin
clopidogrel
warfarin

Gastric irritation due to aspirin can be caused by infection of this microorganism: ___________

Helicobacter pylori

Gastric irritation due to aspirin can be caused by history of _________ or ___________

peptic ulcer or gastric bleeding

Gastric irritation due to aspirin can be caused by (YOUNGER / OLDER) age

older

Gastric irritation due to aspirin can be caused by presence of ___________________

other severe comorbidities

Aspirin must not be given to children recovering from (BACTERIAL / VIRAL) infection,
as it can cause ______________ (swelling in the liver and brain)

Reye’s syndrome

Aspirin was synthesized by the (TURKISH / GERMAN) chemist: _______________ at the end of the ___th century

german chemist
felix hofmann
19th century

the initial preparation of aspirin consists of an ____________ reaction catalyzed by _________ where salicylic acid is treated with ____________ gives acetylsalicylic acid.

esterification reaction
acid
acetic anhydride

in the reaction of salicylic acid with acetic anhydride, a hydroxyl group is converted into an __________, with _________ as byproduct

ester
acetic acid

when aspirin is reacted with FERRIC CHLORIDE solution, it will form ___________________

no color change

aspirin elicits no color change in ferric chloride test due to lacking a __________ group

phenol group

when aspirin is reacted with SODIUM HYDROXIDE solution, it will undergo ________ reaction, forming ________________

neutralization
sodium acetylsalicylate and water

A ______ (normality) sulfuric acid solution can be used to neutralize the excess NaOH and to determine the amount of aspirin present through titration.

2N sulfuric acid

___________ must be stored at room temperature and away from excess heat and moisture, and any vinegar odor-like smell that may produce from the medication must be disposed immediately.

aspirin

Fill in the blanks with the correct step number in synthesizing aspirin from salicylic acid.

___ Add carefully 5 to 10 drops of 85% phosphoric acid to the flask and swirl to mix thoroughly.
___ Weigh 3g of salicylic acid and place it in a 250 ml Erlenmeyer flask.
___ Add another 20 ml of water and cool in an ice bath. Scratch the walls of the flask with a stirring rod to induce crystallization.
___ Measure 6 ml of acetic anhydride and add it to the flask. (Note: Do this inside the hood and wear goggles.)
___ Filter the solid aspirin through a piece of pre-weighed filter paper using a funnel.
___ Weigh the product and calculate the percentage yield.
___ Heat the mixture for about 10 minutes in a beaker with warm water (78-80°C).
___ Wash the crystals with 2-3ml chilled water.
___ Add cautiously 20 drops of distilled water.
___ Place the filter with the product on a watch glass and put it in the oven at 100°C for about 30 minutes until dry.

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