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Nicergoline

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Nicergoline Basic information
Nicergoline Chemical Properties
  • Melting point:136-138°
  • Boiling point:594.4±50.0 °C(Predicted)
  • Density 1.3558 (rough estimate)
  • refractive index 1.6200 (estimate)
  • storage temp. 2-8°C
  • solubility Practically insoluble in water, freely soluble in methylene chloride, soluble in ethanol (96 per cent).
  • form neat
  • pka6.33±0.40(Predicted)
  • Water Solubility Soluble in alcohol, chloroform, and acetone. Insoluble in water.
  • Merck 14,9496
Safety Information
  • Hazard Codes Xn
  • Risk Statements 22
  • Safety Statements 36
  • RIDADR 1544
  • WGK Germany 3
  • RTECS KE6341000
  • HazardClass 6.1(b)
  • PackingGroup III
  • HS Code 29396100
  • ToxicityLD50 in male mice, rats (mg/kg): 860, 2800 orally; 46, 43 i.v. (Neumann, Lauschner)
MSDS
Nicergoline Usage And Synthesis
  • Chemical PropertiesFine to granular, white or yellowish powder.
  • OriginatorSermion,Farmitalia,Italy,1974
  • Usesantipsychotic
  • Manufacturing ProcessPreparation of 1-Methyl Lumilysergic Acid 8-Methyl Ester-10-Methyl Ether: Into a suspension of 10 grams of 1-methyl-lumilysergic acid in 600 cc of absolute methanol a stream of anhydrous hydrogen chloride is bubbled for 1.5 hours with strong cooling. The stream of hydrogen chloride is stopped and the mixture is allowed to stand for 30 minutes at 0°C, and is evaporated in vacuo to dryness. The residue is taken up with ice-cooled water made alkaline with concentrated ammonia and extracted with chloroform. The combined chloroform extracts are washed first with a 5% aqueous solution of sodium bicarbonate, then with water, and are thereafter dried over anhydrous sodium sulfate and finally evaporated in vacuo to dryness.
    Preparation of 1-Methyl Lumilysergol-10-Methyl Ether: To a boiling suspension of 2 grams of lithium aluminum hydride in 50 cc of anhydrous tetrahydrofuran, a solution of 1 gram of 1-methyl lumilysergic acid-8-methyl ester-10-methyl ether in 20 cc of anhydrous tetrahydrofuran is added dropwise and the resulting solution is refluxed for a further 2 hours. After cooling the resulting solution, aqueous tetrahydrofuran is added to destroy the excess reducing agent and the solution is filtered. Tetrahydrofuran is distilled off and the residue is recrystallized from acetone petroleum ether.
    Preparation of Nicergoline: To a solution of 1-methyl lumilysergol-10-methyl ether in pyridine, 5-bromonicotinyl chloride is used as an acylating agent at room temperature. The mixture is stirred for 1 hour. Water and methanol are added and the resulting mixture is stirred for 1 hour, extracted with chloroform, and washed in sequence with 1% aqueous caustic soda, 5% aqueous sodium bicarbonate solution, and water. The resulting solution is dried over anhydrous sodium sulfate and the solvent is distilled off. By recrystallization of the residue from acetone petroleum ether, nicergoline is obtained, melting at 136° to 138°C.
  • brand nameSermion (Farmitalia, Societa Farmaceutici Italia, Italy).
  • Therapeutic FunctionVasodilator
  • Biological Activityα -adrenergic, vasodilator. Cognitive enhancer.
  • Safety ProfilePoison by intravenous route. Moderately toxic by ingestion and subcutaneous routes. An experimental teratogen. Other experimental reproductive effects. A vasodilator. When heated to decomposition it emits very toxic fumes of Brand NOx.
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