Phenacetin
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| ECHA InfoCard | 100.000.485 |
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| Formula | C10H13NO2 |
| Molar mass | 179.216 g/mol |
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| Density | 1.24 g/cm3 |
| Melting point | 134 °C (273 °F) (decomposes) |
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Phenacetin (or acetophenetidin) is a pain-relieving and fever-reducing drug, which was widely used between its introduction in 1887 and the 1983 ban imposed by the FDA on its use in the United States. Its use has declined because of its adverse effects, which include increased risk of certain cancers and kidney damage. It is metabolized as paracetamol (acetaminophen), which replaced it in some over-the-counter medications following the ban on phenacetin.
Phenacetin was introduced in 1887 in Elberfeld by German company Bayer, and was used principally as an analgesic; it was one of the first synthetic fever reducers to go on the market. It is also known historically to be one of the first non-opioid analgesics without anti-inflammatory properties.
Its analgesic effects are due to its actions on the sensory tracts of the spinal cord. In addition, phenacetin has a depressant action on the heart, where it acts as a negative inotrope. It is an antipyretic, acting on the brain to decrease the temperature set point. It is also used to treat rheumatoid arthritis (subacute type) and intercostal neuralgia.
It is metabolised in the body as paracetamol (acetaminophen), which is also a clinically relevant analgesic.
The first synthesis was reported in 1878 by Harmon Northrop Morse.
Phenacetin may be synthesized as an example of the Williamson ether synthesis: ethyl iodide, paracetamol, and anhydrous potassium carbonate are refluxed in 2-butanone to give the crude product, which is recrystallized from water.
Phenacetin was widely used until the third quarter of the twentieth century, often in the form of an "A.P.C." or aspirin-phenacetin-caffeine compound analgesic, as a remedy for fever and pain. An early formulation (1919) was Vincent's APC in Australia. However the U.S. Food and Drug Administration ordered the withdrawal of drugs containing phenacetin in November 1983, owing to its carcinogenic and kidney-damaging properties (Federal Register of October 5, 1983 (48 FR 45466)). It was also banned in India. As a result, some branded, previously phenacetin-based preparations continued to be sold, but with the phenacetin replaced by safer alternatives. A popular brand of phenacetin was Roche's Saridon, which was reformulated in 1983 to contain propyphenazone, paracetamol and caffeine. Coricidin was also reformulated without phenacetin. Paracetamol is a metabolite of phenacetin with similar analgesic and antipyretic effects, but the new formulation has not been found to have phenacetin's carcinogenicity.
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