Ergometrinine
Title: Ergometrinine
CAS Registry Number: 479-00-5
CAS Name: [8a(S)]-9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergolinecarboxamide
Additional Names: D-lysergic acid D-propanolamide; ergonovinine
Molecular Formula: C19H23N3O2
Molecular Weight: 325.40
Percent Composition: C 70.13%, H 7.12%, N 12.91%, O 9.83%
Literature References: An alkaloid isomeric with ergonovine, q.v. Ergometrinine and ergonovine can be interconverted by simple chemical procedures: Smith, Timmis, J. Chem. Soc. 1936, 1166. Chromatographic determn in cereal grains: G. H. Ware et al., J. Assoc. Off. Anal. Chem. 69, 697 (1986).
Properties: Stout prisms from acetone, dec 196°. [a]D20 +416° (c = 0.45 in chloroform). pK 7.3. Freely sol in pyridine, moderately in chloroform; slightly sol in alcohol, acetone. Nearly insol in water.
pKa: pK 7.3
Optical Rotation: [a]D20 +416° (c = 0.45 in chloroform)
 
Derivative Type: Hydrobromide monohydrate
Molecular Formula: C19H24BrN3O2.H2O
Molecular Weight: 424.33
Percent Composition: C 53.78%, H 6.18%, Br 18.83%, N 9.90%, O 11.31%
Properties: Needles from aq acetone + ether, dec 190°.
 
Derivative Type: Hydrochloride monohydrate
Molecular Formula: C19H24ClN3O2.H2O
Molecular Weight: 379.88
Percent Composition: C 60.07%, H 6.90%, Cl 9.33%, N 11.06%, O 12.64%
Properties: Needles, dec 175-180°.
 
Derivative Type: Mononitrate
Molecular Formula: C19H24N4O5
Molecular Weight: 388.42
Percent Composition: C 58.75%, H 6.23%, N 14.42%, O 20.60%
Properties: Stout prisms from aq MeOH + ether, dec 235°. [a]D20 +282° (c = 1).
Optical Rotation: [a]D20 +282° (c = 1)
 
Derivative Type: Perchlorate
Molecular Formula: C19H24ClN3O6
Molecular Weight: 425.86
Percent Composition: C 53.59%, H 5.68%, Cl 8.33%, N 9.87%, O 22.54%
Properties: Needles, dec 225° (brown at 210°).

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