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METERGOLINE Basic information
METERGOLINE Chemical Properties
  • Melting point:148-150 °C(lit.)
  • alpha D28 -7 ±2°
  • Boiling point:612.5±55.0 °C(Predicted)
  • Density 1.25±0.1 g/cm3(Predicted)
  • storage temp. −20°C
  • solubility 0.1 M HCl: 1.4 mg/mL
  • pka12.45±0.46(Predicted)
  • Merck 13,5962
  • CAS DataBase Reference17692-51-2(CAS DataBase Reference)
Safety Information
  • Hazard Codes Xn
  • Risk Statements 20/21/22
  • Safety Statements 36
  • WGK Germany 3
  • RTECS FA1070000
  • ToxicityLD50 in mice (mg/kg): 85 i.p., 430 orally; in rats (mg/kg): >800 orally (Beretta)
METERGOLINE Usage And Synthesis
  • Chemical PropertiesWhite Solid
  • OriginatorLiserdol,Farmitalia,Italy,1970
  • UsesMetergoline is an antagonist at 5-HT1, 5-HT2, and 5-HT7 serotonin receptors. Metergoline is an analgesic; antipyretic.
  • Manufacturing Process16 g of 1-methyl-dihydro-lysergamine (the 10-position hydrogen has the αconfiguration) are dissolved in 80 cc of anhydrous pyridine by mildly heating. To the solution, cooled to -10°C and stirred, 18 cc of 85% carbobenzoxychloride (in toluene) diluted in 36 cc of chloroform are added dropwise, rather rapidly. The mixture is kept at -10°C during the addition, and for 10 minutes afterwards. The cooling means is removed and the temperature is allowed to rise to room level in 10 minutes. The reaction mixture is diluted with 240 cc of chloroform and rapidly washed with 80 cc of 5% aqueous sodium hydroxide solution, with saturated aqueous sodium bicarbonate solution, and finally with water.
    The chloroform solution is briefly dried over anhydrous sodium sulfate and evaporated to dryness in vacuo at 40°C. The oily residue is taken up in 160 cc of benzene and passed through a column containing 48 g of alumina. The column is then eluted with further 160 cc of benzene. The collected eluates are evaporated in vacuo at 40°C. The thick oily residue is mixed with a small amount of anhydrous diethyl ether. After some time a crystalline mass is obtained, which is collected and washed with a small amount of benzene and diethyl ether. 12 g of white crystals are obtained, melting at 146° to 148°C.
  • Therapeutic FunctionAnalgesic
  • Biological ActivityAntagonist at 5-HT 1 /5-HT 2 with activity at 5-HT 1D . Has moderate affinity for 5-HT 6 and high affinity for 5-HT 7 .
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