Metergoline
Title: Metergoline
CAS Registry Number: 17692-51-2
CAS Name: [[(8b)-1,6-Dimethylergolin-8-yl]methyl]carbamic acid phenylmethyl ester
Additional Names: D-8b-[(carbobenzoxyamino)methyl]-1,6-dimethyl-10a-ergoline; D-N-carbobenzoxydihydro-1-methyllysergamine I; D-8b-[(carboxyamino)methyl]-1,6-dimethylergoline I benzyl ester; D-N-carboxydihydro-1-methyllysergamine I benzyl ester; D-[(4,6,6a,7,8,9,10,10a-octahydro-4,7-dimethyl-10aa-indolo[4,3-fg]quinolin-9b-yl)methyl]carbamic acid benzyl ester; methergoline
Trademarks: Liserdol (Farmitalia); Contralac (Virbac)
Molecular Formula: C25H29N3O2
Molecular Weight: 403.52
Percent Composition: C 74.41%, H 7.24%, N 10.41%, O 7.93%
Literature References: Serotonin 5HT-receptor antagonist. Prepn: Bernardi et al., Gazz. Chim. Ital. 94, 936 (1964); Camerino et al., US 3238211 (1966 to Farmitalia). Pharmacology: C. Beretta et al., Nature 207, 421 (1965). Metabolic studies: Arcamone et al., Boll. Chim. Farm. 110, 704 (1971). Mode of action study: L. Krulich et al., Endocrinology 108, 1115 (1981). Clinical antiprolactin activity: F. Scapin et al., Eur. J. Clin. Pharmacol. 22, 181 (1982); A. Caballero et al., J. Reprod. Med. 32, 115 (1987).
Properties: Crystals from benzene + ether, mp 146-149°. [a]D28 -7 ±2°. uv max: 291 nm (E1%1cm 165). Very sol in pyridine; sol in alc, acetone, chloroform. Practically insol in benzene, ether, water. LD50 in mice (mg/kg): 85 i.p., 430 orally; in rats (mg/kg): >800 orally (Beretta).
Melting point: mp 146-149°
Optical Rotation: [a]D28 -7 ±2°
Absorption maximum: uv max: 291 nm (E1%1cm 165)
Toxicity data: LD50 in mice (mg/kg): 85 i.p., 430 orally; in rats (mg/kg): >800 orally (Beretta)
Therap-Cat: Prolactin inhibitor.
Therap-Cat-Vet: Prolactin inhibitor.
Keywords: Prolactin Inhibitor.

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