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6-Mercaptopurine

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6-Mercaptopurine Basic information
6-Mercaptopurine Chemical Properties
  • Melting point:241-244°C
  • Boiling point:498.6±37.0 °C(Predicted)
  • Density 1.463 (estimate)
  • refractive index 1.5605 (estimate)
  • storage temp. Inert atmosphere,2-8°C
  • form solid
  • pka7.77, 11.17(at 25℃)
  • Water Solubility 124mg/L(25 ºC)
  • CAS DataBase Reference50-44-2(CAS DataBase Reference)
  • IARC3 (Vol. 26, Sup 7) 1987
  • EPA Substance Registry SystemMercaptopurine (50-44-2)
Safety Information
6-Mercaptopurine Usage And Synthesis
  • Chemical PropertiesYellowish-Greenish Solid
  • OriginatorPurinethol,Sandoz,France,1950
  • Usesantineoplastic, immonusupressant;inhibits purine nucleotide synthesis and metabolism
  • UsesHas a cytotoxicity effect
  • DefinitionA sulfurcontaining purine base not found in animal nucleoproteins.
  • Manufacturing Process7.5 g of 4-amino-6-chloro-5-nitropyrimidine was suspended in 200 ml of 1 N potassium hydrosulfide and heated on the steam bath for 2 hours while passing hydrogen sulfide through the reaction mixture. The reaction mixture was allowed to cool slowly, acidified with 10 N sulfuric acid and chilled. The precipitate consisted of 4,5-diamino-6-mercaptopyrimidine and sulfur. It was boiled with 300 ml of water, filtered hot and then chilled. The product precipitated as pale yellow needles (4.2 g); an additional 0.95 g was obtained by concentration of the mother liquors to 100 ml.
    A mixture of 2 g of 4,5-diamino-6-mercaptopyrimidine and 10 ml of 98% formic acid was heated at 70°C for two hours and then evaporated to dryness on the steam bath to give as a residue, 7-amino-thiazolo (5,4-d) pyrimidine.
    To 820 mg of 7-amino-thiazolo[5,4-d]pyrimidine was added 2.5 cc of 2 N sodium hydroxide. The water was removed under reduced pressure. The sodium salt was then heated at 240°C for one hour, during which time it melted, gave off water and resolidified. The sodium salt of 6-mercaptopurine was dissolved in 15 ml of water and acidified to pH 5 with acetic acid. Yellow crystals of 6-mercaptopurine hydrate precipitated, according to US Patent 2,933,498.
  • brand namePurinethol (Teva).
  • Therapeutic FunctionCancer chemotherapy
  • HazardQuestionable carcinogen.
  • Safety ProfilePoison by ingestion, intraperitoneal, subcutaneous, parenteral, and intravenous routes. Human systemic effects by ingestion: dermatitis. Experimental teratogenic and reproductive effects. Questionable human carcinogen producing Hodgkin's disease and leukemia. Human mutation data reported. When heated to decomposition it emits very toxic fumes of SOx and NOx. See also MERCAPTANS.
  • Veterinary Drugs and TreatmentsVeterinary uses of mercaptopurine include adjunctive therapy of lymphosarcoma, acute leukemias, and severe rheumatoid arthritis. It may have potential benefit in treating other autoimmune conditions (e.g., unresponsive ulcerative colitis) as well.
6-Mercaptopurine Preparation Products And Raw materials
6-Mercaptopurine (50-44-2)Related Product Information
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