Methylergonovine
Title: Methylergonovine
CAS Registry Number: 113-42-8
CAS Name: (8b)-9,10-Didehydro-N-[(1S)-1-(hydroxymethyl)propyl]-6-methylergoline-8-carboxamide
Additional Names: N-[a-(hydroxymethyl)propyl]-D-lysergamide; D-lysergic acid (+)-butanolamide-(2); d-lysergic acid-d-1-hydroxybutylamide-2; methylergometrine; methylergobasine
Molecular Formula: C20H25N3O2
Molecular Weight: 339.43
Percent Composition: C 70.77%, H 7.42%, N 12.38%, O 9.43%
Literature References: Semisynthetic ergot alkaloid; metabolite of methysergide, q.v. Prepn: A. Stoll, A. Hofmann, US 2265207 (1941 to Sandoz); eidem, Helv. Chim. Acta 26, 944 (1943). HPLC determn in plasma: H. T. Smith, N. C. Molinaro, J. Chromatogr. 424, 416 (1988). Clinical trial in prevention of cluster headache: L. Mueller et al., Headache 37, 437 (1997). Review of pharmacology and clinical use in obstetrics and gynecology: A. N. de Groot et al., Drugs 56, 523-535 (1998).
Properties: Shiny crystals from benzene, mp 172° (some decompn). [a]D20 -45° (c = 0.4 in pyridine). Sparingly sol in water. Freely sol in alcohol, acetone.
Melting point: mp 172° (some decompn)
Optical Rotation: [a]D20 -45° (c = 0.4 in pyridine)
 
Derivative Type: Maleate
CAS Registry Number: 57432-61-8
Trademarks: Basofortina (Novartis); Methergin (Novartis); Methergine (Novartis); Metenarin (Teikoku Zoki); Methylergobrevin (Wernigerode); Ryegonovin (Aventis); Spametrin-M (Yamanouchi Seiyaku)
Molecular Formula: C20H25N3O2.C4H4O4
Molecular Weight: 455.50
Percent Composition: C 63.28%, H 6.42%, N 9.23%, O 21.07%
Properties: White to pinkish-tan microcryst powder; odorless; bitter taste. Slightly sol in water, alcohol; very slightly sol in chloroform, ether.
 
Therap-Cat: Oxytocic.
Keywords: Oxytocic.

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