Phenacetin

Basic Info

 

Product name: Phenacetin powder

Alias: para-Acetophenetidide

CAS No.: 62-44-2

Specification: Pharmaceitical grade, USP42 EP9.0 Standard

Density: 1.0±0.1 g/cm3

Boiling Point: 323.6±44.0 °C at 760 mmHg

Melting Point(oC): 133-136 °C(lit.)

Molecular Formular: C10H13NO2

Molecular Weight: 179.216

Flash Point: 149.5±28.4 °C

Exact Mass: 179.094635

Phenacetin, and products containing phenacetin, have been shown in an animal model to have the side effect and after-effect of carcinogenesis. In humans, many case reports have implicated products containing phenacetin in urothelial neoplasms, especially urothelial carcinoma of the renal pelvis. In one prospective series, phenacetin was associated with an increased risk of death due to urologic or renal diseases, death due to cancers, and death due to cardiovascular diseases. In addition, people withglucose-6-phosphate dehydrogenase deficiency may experience acutehemolysis, or dissolution of blood cells, while taking this drug. Acute hemolysis is possible in the case of patients who develop an IgMresponse to phenacetin leading to immune complexes that bind to erythrocytes in blood. The erythrocytes are then lysed when the complexes activate thecomplement system.

The antipyretic and analgesic effect of phenacetin is similar to "acetylsalicylic acid". It is mainly used as an antipyretic and analgesic. The effect is slow and long lasting. It has good curative effect on the treatment of headache, neuralgia, arthralgia and fever. But its anti-rheumatic and anti-inflammatory effects are weak. Excessive doses can cause methemoglobinemia and cause hypoxia in the body. Long-term medication can damage the kidneys and even cause nipple necrosis. It should be used with caution. Due to its toxic side effects and the rapid development of other similar drugs, the drug has ceased to be used alone, but used as a compound preparation for raw materials and other drugs.

Phenacetin is a white crystalline powder with the chemical composition C10H13NO2. It was first developed by Harmon Northrop Morse in 1878. In addition to its pain-reducing properties, it also has been used as a fever-reducer, a treatment for rheumatoid arthritis and a treatment for intercostal neuralgia, a rare disorder that causes pain in the nerves around the ribs. It was one of the first painkillers that was not derived from opium while at the same time being absent of anti-inflammatory qualities.

Phenacetin is a non-opioid analgesic that was commonly used as an over-the-counter pain reliever in the past. Phenacetin is often marketed as a painkiller and cough suppressant in combination with other ingredients such as paracetamol (acetaminophen) or aspirin. Phenacetin has been extensively studied for its activities, including its effects on the central nervous system and the cardiovascular system. It is known to be a centrally acting analgesic that blocks the transmission of pain signals to the brain. Phenacetin is also believed to have antipyretic (fever-reducing) properties and may have some local anesthetic effects.

Phenacetin is obtained by acetylation of p-aminophenethyl ether. Heat the mixture of benzene, acetic anhydride and p-aminophenethyl ether on an oil bath to azeotrope for 4 hours. After the reaction is completed, the reactant is cooled to precipitate Phenacetin, which is filtered, washed with cold benzene, and dried. The yield of Phenacetin is the theoretical amount. 86% of it. It can also use acetic acid instead of benzene as a solvent. Heat 40% dilute acetic acid to boiling. Put in p-aminophenethyl ether. Distill off the water, then add glacial acetic acid when the temperature rises to 150℃. Reflux for 1 hour and continue to steam. Wait for the temperature to rise above 150℃, sample and determine free aminobenzene Diethyl ether. Add acetic anhydride according to the amount of residual amino phenyl ethyl ether, reflux reaction for 0.5h. Check the end point. Depressurize after passing, recover acetic acid until the amino content is below 0.046 and the acid content is below 0.2%. Then the reaction is hydraulically put into the hot refined mother liquor, Stir and lower the temperature to 40°C and filter to obtain crude Phenacetin. Add boiling water or refined mother liquor to the crude Phenacetin, then heat and stir to dissolve. Adjust the filtrate with acid to pH 4.5-4.7, add activated carbon and sodium thiosulfate to stir to decolorize. Cool the filtrate to crystallize and spin filter through dry air flow to get Phenacetin.

Phenacetin can also be obtained by the action of acetaminophen and sodium ethoxide. At first, add p-acetamidophenol to sodium ethoxide. Then slowly add ethyl iodide, heat to reflux for 1 hour, cooling and filtering. The resulting crude product is dissolved in ethanol. After filtering, the filtrate is diluted with hot water, then cooled, filtered, and dried to obtain Phenacetin. The output of Phenacetin is 80% of the theoretical amount.

Phenacetin is an acetanilide antipyretic and analgesic. Phenacetin has mild and lasting antipyretic and analgesic effect. The antipyretic effect of Phenacetin is similar to that of Aspirin, but the analgesic effect is weaker. Phenacetin has few anti-inflammatory, anti-rheumatic and anti-platelet aggregation effects. Due to the greater toxicity of Phenacetin, as well as the replacement of paracetamol with similar effects and less toxicity, Phenacetin is no longer used alone. Phenacetin is only used in compound preparations with aspirin, aminopyrine, and barbiturates.

The antipyretic effect of Phenacetin is stronger than the analgesic effect. The potency of Phenacetin is equivalent to that of Aspirin. Phenacetin and its metabolite paracetamol have antipyretic effects. This is because when Phenacetin cannot be converted into paracetamol with enzyme inhibitors, Phenacetin can still show a significant antipyretic effect. Therefore, the antipyretic effect of Phenacetin that appears after the Phenacetin is given is not only produced by its active product paracetamol. The mild analgesic effect of Phenacetin can generally be maintained for 3-4 hours. The synergistic effect of Phenacetin combining with salicylic acid enhances the analgesic effect. Clinically, Phenacetin is mainly used for antipyretic and analgesic in small animals. Phenacetin is also one of the components of APC tablets.

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