Methysergide
Title: Methysergide
CAS Registry Number: 361-37-5
CAS Name: (8b)-9,10-Didehydro-N-[(1S)-1-(hydroxymethyl)propyl]-1,6-dimethylergoline-8-carboxamide
Additional Names: N-[1-(hydroxymethyl)propyl]-1-methyl-D-lysergamide; 1-methylmethylergonovine; 1-methyl-d-lysergic acid butanolamide; 1-methyl-d-lysergic acid (+)-1-hydroxy-2-butylamide
Manufacturers' Codes: UML-491
Molecular Formula: C21H27N3O2
Molecular Weight: 353.46
Percent Composition: C 71.36%, H 7.70%, N 11.89%, O 9.05%
Literature References: Serotonin receptor antagonist. Prepn: GB 854569 (1960); A. Hofmann, F. Troxler, US 3113133 (1963 to Sandoz). Comparative pharmacology: Z. Votava et al., Arzneim.-Forsch. 16, 220 (1966); P. N. Chambers, P. B. Marshall, J. Pharm. Pharmacol. 19, 65 (1967). Mechanism of action: D. A. Curran et al., Res. Clin. Stud. Headache 1, 74 (1967); J. E. Hardebo et al., Neurology 28, 64 (1978); S. W. J. Lamberts, R. M. Mac Leod, Endocrinology 103, 287 (1978).
Properties: Crystals, mp 194-196°. [a]D20 -45° (c = 0.5 in pyridine).
Melting point: mp 194-196°
Optical Rotation: [a]D20 -45° (c = 0.5 in pyridine)
 
Derivative Type: Tartrate
Molecular Formula: C46H60N6O10
Molecular Weight: 857.00
Percent Composition: C 64.47%, H 7.06%, N 9.81%, O 18.67%
Properties: Crystals, sparingly sol in water.
 
Derivative Type: Dimaleate
Properties: Dec ~165°. Sol in methanol, less sol in water (1:250). Practically insol in abs ethanol.
 
Derivative Type: Hydrogen maleate
CAS Registry Number: 129-49-7
Additional Names: Methysergide maleate
Trademarks: Deseril (Novartis); Désernil (Novartis); Sansert (Novartis)
Molecular Formula: C21H27N3O2.C4H4O4
Molecular Weight: 469.53
Percent Composition: C 63.95%, H 6.65%, N 8.95%, O 20.45%
 
Therap-Cat: Antimigraine.
Keywords: Antimigraine; Serotonin Receptor Agonist; Serotonin Receptor Antagonist.

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