Research Chemicals for Lab Use

PHENACETIN Synthesis, SAR, MCQ, Structure, Chemical Properties and Therapeutic Uses

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Phenacetin

IUPAC nomenclature

N-(4-Ethoxyphenyl)acetamide

Classification

• NSAID
• Acetamide
• Non-narcotic analgesic

Physiochemical Properties

Mechanism of Action

• Phenacetin produces actions on sensory tracts of the spinal cord and produces analgesic effects.
• Drug also produces depressant actions on the heart by acting as a negative inotropic agent.
• It also produces effects on the heat-controlling centers in the brain to act as an antipyretic rug.
• In the body, it converts into acetaminophen which also a relevant analgesic and antipyretic agent.

Structure Activity Relationship

SAR of phenacetin and acetaminophen can be summarized as follows:

• Aminophenols are less toxic than corresponding aniline.
• Etherification of the phenolic function with methyl or propyl groups results in the derivatives having greater side effects than with ethyl groups.
• Substitution on the nitrogen with such groups that decreases the basicity also reduces the activity of the drug.
• Amides derived from aromatic acids are less active or inactive. [1]

Method of synthesis

i. Reaction of p-amiophenol with acetic anhydride to produce acetaminophen.

ii. Acetaminophen is treated with anhydrous potassium carbonate, ethyl iodide and 2-butanone at reflux to produce phenacetin.

Therapeutic Uses

Phenacetin is used for:

• Anti-inflammatory drug
• Antipyretic
• Analgesic
• Treatment of subacute rheumatoid arthritis
• Treatment of intercost