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Levamisole hydrochloride

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Levamisole hydrochloride Basic information
Levamisole hydrochloride Chemical Properties
  • Melting point:266-267 °C(lit.)
  • alpha -128 º (c=5, H2O)
  • refractive index -126 ° (C=1, H2O)
  • Flash point:9℃
  • storage temp. 2-8°C
  • solubility Freely soluble in water, soluble in ethanol (96 per cent), slightly soluble in methylene chloride.
  • form Crystalline Powder
  • color White to almost white
  • Water Solubility 210 g/L (20 ºC)
  • Merck 14,5459
  • BRN 4358988
  • CAS DataBase Reference16595-80-5(CAS DataBase Reference)
  • EPA Substance Registry SystemLevamisole hydrochloride (16595-80-5)
Safety Information
Levamisole hydrochloride Usage And Synthesis
  • Chemical PropertiesWhite to almost white crystalline powder
  • OriginatorSolaskil,Specia,France,1971
  • UsesBiological response modifier with anthelmintic activity. Anthelmintic (nematodes); immunomodulator.
  • Usesantifungal
  • Manufacturing ProcessTo a stirred and refluxed suspension of 17 parts of 1,2-dibromoethane, 7.8 parts of sodium hydrogen carbonate and 50 parts of 2-propanol is added a mixture of 3.4 parts of dl-2-thio-1-phenyl-imidazolidine, 9 parts of a 20% potassium hydroxide solution in 40 parts of 2-propanol over a period of about 1 hour. After the addition is complete, the whole is stirred and refluxed for an additional 3 hours. The reaction mixture is evaporated. To the residue are added 18 parts of a 15% potassium hydroxide solution. The whole is extracted with toluene. The extract is dried and evaporated. The oily residue is dissolved in acetone and gaseous hydrogen chloride is introduced into the solution. The precipitated solid salt is filtered off and recrystallized from 2-propanol, yielding dl-2,3,5,6-tetrahydro-6-phenyl-imidazo[2,1-b]thiazole hydrochloride; melting point 264°C to 266°C.
    dl-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride, 188 g (0.785 mol), is suspended in a mixture of 500 ml of water and 500 ml of methylene chloride. The suspension is stirred mechanically while 20% sodium hydroxide solution is added until the solution is basic. Ice is added from time to time to keep the temperature below the boiling point of the methylene chloride. The methylene chloride layer is separated, washed with water, dried over potassium carbonate and evaporated. The oily residue crystallizes with the evolution of the heat when poured into a beaker containing 100 ml of ether. The free base is washed with ether. The yield of dl-6-phenyl-2,3,5,6- tetrahydroimidazo[2,-b]thiazole is 151.4 g (0.746 mol), 94%. The product has a melting point of 90°C.
    A solution of 204.3 g (1 mol) of dl-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1- b]thiazole and 232.3 g (1 mol) of d-10-camphorsulfonic acid in 1,750 ml of chloroform is allowed to crystallize overnight at -28°C. The solvate is recovered by filtration and washed with ice cold chloroform (400 ml). The solvate is dried (decomposed) under nitrogen 7 hours and then in air overnight. The yield of d(+)6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole d-10-camphorsulfonate is 202.5 g (0.464 mol) 92.8%, melting point 139°C to 140°C [α]D25+ 82.6 (C = 16, H2O).
    A solution of 150 g (0.344 mol) of d(+)6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole, d-10-camphorsulfonate in water is treated with 15.5 g (0.378 mol) of 98% sodium hydroxide and the liberated base extracted with chloroform. The chloroform solution is washed with water followed by sodium chloride solution and dried over magnesium sulfate. Evaporation of the solvent left 72.1 g of residue which crystallized shortly. The free base hereby obtained has a melting point of 60°C to 61.5°C and an optical rotation [α]D25+ 85.1 (C = 10, CHCl3).
    The free base d(+)6-phenyl-2,3,5.6-tetrahydroimidazo[2.1-b]thiazole is dissolved in 112 ml of acetone and 178 ml of isopropanolic hydrogen chloride is added all at once. The hydrochloride crystallizes at once. After cooling to below 0°C, the salt is recovered by filtration and washed with acetone. The product weighs 75.2 g (0.312 mol), 91%, from the camphorsulfonate, melting point 227°C to 227.5°C [α]D25+ 123.1 (C = 15, H2O).
  • brand nameErgamisol (Janssen);Vermisol.
  • Therapeutic FunctionAntiinflammatory
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