Methysergide

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Structural formula
Structural formula of methysergide
General
Non-proprietary name Methysergide
other names

1-methyl- D -lysergic acid (1-hydroxybut-2-yl) amide ( IUPAC )

Molecular formula C 21 H 27 N 3 O 2
Brief description

colorless to yellowish solid (maleate salt)

External identifiers / databases
CAS number
  • 361-37-5
  • 129-49-7 (maleate)
EC number 206-644-0
ECHA InfoCard 100.006.041
PubChem 9681
ChemSpider 9300
DrugBank DB00247
Wikidata Q424442
Drug information
ATC code

N02 CA04

properties
Molar mass 353.46 g · mol -1
Physical state

firmly

Melting point

194-196 ° C

solubility
  • 2 mg ml −1 in water (maleate)
  • > 10 mg ml −1 in DMSO (maleate)
  • > 20 mg ml −1 in methanol (maleate)
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 301
P: 301 + 310
Toxicological data

440 mg kg −1 ( LD 50 ,  mouse ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Methysergide is a drug that has been used in the preventive treatment of migraines . It acts as an antagonist or partial agonist on various serotonin receptors (5-HT receptors). Its migraine prophylactic effect has been associated in particular with an inhibition of 5-HT 2B . Methysergide was withdrawn from the market due to severe side effects, particularly retroperitoneal fibroses , pleural fibroses , pleural effusions and heart valve fibroses.

Individual evidence

  1. ↑ a b c d e f data sheet Methysergide maleate salt from Sigma-Aldrich , accessed on May 12, 2017 ( PDF ).
  2. ↑ a b entry on methysergide. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.
  3. ↑ Schmuck K, Ullmer C, Kalkman HO, Probst A, Lubbert H: Activation of meningeal 5-HT2B receptors: an early step in the generation of migraine headache? . In: Eur. J. Neurosci. . 8, No. 5, May 1996, pp. 959-967. PMID 8743744 .
  4. ↑ Berthold Jany, Tobias Welte: Pleural effusion in adults - causes, diagnosis and therapy. In: Deutsches Ärzteblatt. Volume 116, No. 21, (May) 2019, pp. 377-385, here: p. 380.
  5. ↑ Koehler PJ, Tfelt-Hansen PC: History of methysergide in migraine . In: Cephalalgia . 28, No. 11, November 2008, pp. 1126-1135. doi : 10.1111 / j.1468-2982.2008.01648.x . PMID 18644039 .