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• Chemical Properties

  Phenacetin occurs at room temperature as white, odorless monoclinic prisms. It is soluble in water (more so in hot than cold water), alcohol, glycerol, and acetone and is slightly soluble in benzene. It is unstable to oxidizing agents, iodine, and nitrating agents (IARC 1977).;

• Uses

  Phenacetin was used as an analgesic and fever-reducing drug in both human and veterinary medicine for many years. It was introduced into therapy in 1887 and was extensively used in analgesic mixtures until it was implicated in kidney disease (nephropathy) due to abuse of analgesics (Flower et al. 1985) and was withdrawn from the U.S. market in 1983 (Ronco and Flahault 1994, FDA 1998, 1999). Phenacetin also was previously used as a stabilizer for hydrogen peroxide in hair-bleaching preparations (IARC 1980, HSDB 2009).;

• 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.” ;

• Carcinogenicity

  Phenacetin is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
  Cancer Studies in Experimental Animals
  Dietary administration of phenacetin caused benign and malignant tumors of the urinary tract in mice and rats of both sexes and of the nasal cavity (adenocarcinoma, squamous-cell carcinoma, and transitional-cell carcinoma) in rats of both sexes (Isaka et al. 1979, IARC 1980).
  Cancer Studies in Humans
  There is limited evidence for the carcinogenicity of phenacetin in humans. There are numerous case reports of kidney cancer (transitionalcell carcinoma of the renal pelvis) among patients who had consumed large amounts of analgesic mixtures containing phenacetin; however, it is not possible to specify which component(s) of the mixture is carcinogenic (IARC 1977, 1980).
  https://ntp.niehs.nih.gov/ntp/roc/content/profiles/phenacetinandanalgesicmixtures.pdf ;

• Synthesis of Phenacetin

  The preparation of phenacetin is a straightforward, two-step “one-pot” organic synthesis.
  In a 10-mL Erlenmeyer flask place 0.20 g (1.46 mmol) of p-phenetidine (MW 137) and 3.50 mL of water.
  Add 4 drops only (about 1.0 mmol) of concentrated (12 M) hydrochloric acid, which should dissolve the amine completely. Do not be concerned if some undissolved material remains. Add a spatula-tip of activated carbon (decolorizing charcoal) to the solution, swirl the solution on a hot plate for a few minutes, and remove the charcoal by pipette filtration into a clean 10-mL flask.
  Note: If a very slight color persists in the pphenetidine hydrochloride solution, do not repeat the decolorizing procedure but continue with the remainder of the experiment. If the solution is fairly dark, however, a second decolorizing charcoal treatment may be necessary.
  Prepare a weakly basic solution by dissolving 0.24 g (2.92 mmol) of sodium acetate (MW 82) in 0.80 mL of water in a 10-mL flask. Set this solution aside for later use.
  Warm the p-phenetidine hydrochloride solution on a hot plate. Add 0.20 mL (0.22 g, 2.20 mmol) of acetic anhydride (MW 102) while swirling the solution. Add the sodium acetate solution all at once, and swirl the solution vigorously to insure mixing. Allow the solution to stand at room temperature for 5 minutes. If no crystals form, add 1 or 2 drops of acetic anhydride.
  Cool the reaction mixture by immersing the flask in an ice-water bath, and swirl the mixture vigorously until the crude phenacetin crystallizes. Collect the crystals by suction filtration. Wash the crystals with a portion of cold water.
  Purify the crystals by recrystallization from water. Collect the crystals by suction filtration and air dry the crystals.
  
  https://www.stolaf.edu/people/hansonr/chem253/expt4_2008_phenacetin.pdf ;

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