6070. Methylergonovine

Nomenclature

CAS number: 113-42-8
(8β)-9,10-Didehydro-N-[(1S)-1-(hydroxymethyl)propyl]-6-methylergoline-8-carboxamide; N-[α-(hydroxymethyl)propyl]-d-lysergamide; d-lysergic acid (+)-butanolamide-(2); d-lysergic acid-d-1-hydroxybutylamide-2; methylergometrine; methylergobasine.
C20H25N3O2; mol wt 339.43.
C 70.77%, H 7.42%, N 12.38%, O 9.43%.

Description and 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).

Chemical structure

Properties

Shiny crystals from benzene, mp 172° (some decompn). [α]D20 45° (c = 0.4 in pyridine). Sparingly sol in water. Freely sol in alcohol, acetone.

Derivative

Maleate.

Nomenclature

CAS number: 57432-61-8
Basofortina (Novartis); Methergin (Novartis); Methergine (Novartis); Metenarin (Teikoku Zoki); Methylergobrevin (Wernigerode); Ryegonovin (Aventis); Spametrin-M (Yamanouchi Seiyaku).
C20H25N3O2.C4H4O4; mol wt 455.50.
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.

Therapeutic Category

Oxytocic.

Keywords

Oxytocic