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|Product Categories:||Other APIs;Organics;Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals|
|Phenacetin Chemical Properties|
|Melting point||133-136 °C(lit.)|
|Boiling point||132 °C / 4mmHg|
|density||1.1248 (rough estimate)|
|pka||pKa 2.2(H2O) (Uncertain);3.5(aqueous acetone) (Uncertain)|
|Water Solubility||0.076 g/100 mL|
|Stability:||Stable. Incompatible with strong oxidizing agents, strong acids.|
|CAS DataBase Reference||62-44-2(CAS DataBase Reference)|
|NIST Chemistry Reference||Acetamide, N-(4-ethoxyphenyl)-(62-44-2)|
|EPA Substance Registry System||Acetamide, N-(4-ethoxyphenyl)-(62-44-2)|
|RIDADR||UN 3077 9 / PGIII|
|Hazardous Substances Data||62-44-2(Hazardous Substances Data)|
|Toxicity||LD50 orally in rats: 1.65 g/kg (Boyd)|
|Phenacetin Usage And Synthesis|
|Indications and Usage||Phenacetin is mainly used as an antipyretic analgesic, with slow and lasting effects, treating headaches, neuralgia, joint pain, and fever, and weakly resisting rheumatism and inflammation. Because of toxic side effects and the rapid development of similar drugs, however, it is no longer used alone, only as a raw material in combination with other drugs. Commonly combined with aspirin and caffeine to form a less toxic compound aspirin used to treat the common cold. Can make chlorpheniramine cold tablets by adding a small amount of chlorpheniramine to the above compound, used to treat colds with headache, neuralgia, rheumatism, etc. Can be used as a material for organic synthesis or a pharmaceutical intermediate.|
|Mechanisms of Action||On its own, phenacetin has no antipyretic or analgesic effects. In vivo, acetaminophen and paracetamol are metabolized and decomposed to create the antipyretic and analgesic effects. Its decomposites with ammonia and phenyl either not only have no antipyretic and analgesic effects, but also are major factors in its side effects.|
|Side Effects||Long term use may cause renal papillary necrosis and interstitial nephritis, and even induce renal pelvic cancer and bladder cancer. Phenacetin also makes the hemoglobin to form methemoglobin, decreasing blood oxygen carrying capacity, causing cyanosis. In addition, Phenacetin can cause hemolysis and hemolytic anemia, and is toxic to the retina. Long term use may cause also lead to dependence. Countries including America, Britain, German, and Japan have banned Phenacetin, or required packaging to note that it is “not indicated for long-term usage or large doses.”|
|Chemical Properties||white crystalline powder|
|Uses||Analgesic, antipyretic. Component of APC tablets, analgesic mixture also containing aspirin and caffeine. Phenacetin is reasonably anticipated to be a human carcinogen; analgesic mixtures containing Phenacetin are listed as known human carcinogens.|
|Definition||ChEBI: A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a 4-ethoxyphenyl group.|
|Brand name||[Names previously used: Acetophenetidin; Acetphenetidin.].|
|General Description||Odorless fine white crystalline solid with a lightly bitter taste. Used as an analgesic medicine.|
|Air & Water Reactions||Insoluble in water.|
|Reactivity Profile||Phenacetin react with oxidizing agents, iodine and nitrating agents.|
|Fire Hazard||Flash point data for Phenacetin are not available but Phenacetin is probably combustible.|
|Safety Profile||Confirmed carcinogen producing tumors of the lildney and bladder. A human poison by an unspecified route. Poison by intravenous and possibly other routes. Moderately toxic by several routes. Human systemic effects by ingestion: cyanosis, liver damage, and methemo- globinemiacarboxyhemo-globinemia. Experimental teratogenic data. Other experimental reproductive effects. Mutation data reported. Chronic effects consist of weight loss, insomnia, shortness of breath, weakness, and often aplastic anemia. When heated to decomposition it emits toxic fumes of NOx,.|
|Purification Methods||Crystallise it from H2O or EtOH, and its solubility in H2O is 0.08% (at ~10o) and 1.2% (at ~100o), and in EtOH it is 6.7% (at ~10o) and 36% (at ~100o). Alternatively it can be purified by solution in cold dilute alkali and re-precipitating by addition of acid to neutralisation point. Dry it in air. [Beilstein 13 H 461, 13 IV 1092.]|
|Phenacetin Preparation Products And Raw materials|
|Raw materials||Acetic acid glacial-->Acetic anhydride-->4-Acetamidophenol-->Iodoethane-->Phenetidine-->phenylacetic anhydride|
Phenacetin (or acetophenetidin) is a pain-relieving and fever-reducing drug, which was widely used between its introduction in 1887 and the 1983.
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 metabolized in the body to paracetamol (acetaminophen), which is also a clinically relevant analgesic.
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