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Substance Name: Methysergide maleate [USP]
RN: 129-49-7
UNII: 2U7H1466GH
InChIKey: LWYXFDXUMVEZKS-ZVFOLQIPSA-N

Note

  • An ergot derivative that is a congener of LYSERGIC ACID DIETHYLAMIDE. It antagonizes the effects of serotonin in blood vessels and gastrointestinal smooth muscle, but has few of the properties of other ergot alkaloids. Methysergide is used prophylactically in migraine and other vascular headaches and to antagonize serotonin in the carcinoid syndrome.

Molecular Formulas

  • C21-H27-N3-O2.2C4-H4-O4
  • C21-H27-N3-O2.C4-H4-O4

Molecular Weight

  • 469.535
 

Classification Codes

  • Mutation Data
  • Reproductive Effect
  • Vasoconstrictor (Specific in Migraine)
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Names and Synonyms

Name of Substance

  • Methysergide maleate [USP]

MeSH Heading

  • Methysergide

Synonyms

  • (+)-N-((1-Hydroxymethyl)propyl)-1-methyl-D-lysergamide bimaleate
  • 1-(Hydroxymethyl)propylamide of 1-methyl-(+)-lysergic acid hydrogen maleate
  • 1-Methyl-D-lysergic acid butanolamide dimaleate
  • 9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8beta-carboxamide maleate (1:1) (salt)
  • Deseril
  • Deseril-retard
  • Desernil bismaleate
  • EINECS 204-950-9
  • Ergoline-8-carboxamide, 9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-, (8beta)-, (Z)-2-butenedioate (1:1) (salt)
  • Lysergamide, N-((1-hydroxymethyl)propyl)-1-methyl-, maleate
  • Methysergide bimaleate
  • Methysergide dimaleate
  • Methysergide hydrogen maleate
  • Methysergide maleate
  • NSC 186061
  • Sansert
  • UNII-2U7H1466GH

Systematic Names

  • Ergoline-8-beta-carboxamide, 9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-, maleate (1:1) (salt)
  • Ergoline-8-carboxamide, 9,10-didehydro-N-((1S)-1-(hydroxymethyl)propyl)-1,6-dimethyl-, (8beta)-, (2Z)-2-butenedioate (1:1) (salt)
  • Ergoline-8-carboxamide, 9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-, (8beta)-, (Z)-2-butenedioate (1:1) (salt)
  • Ergoline-8beta-carboxamide, 9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-, maleate (1:2) (salt)
  • Methysergide hydrogen maleate

Registry Numbers

CAS Registry Number

  • 129-49-7

FDA UNII

  • 2U7H1466GH

Other Registry Numbers

  • 1257-58-5
  • 29605-96-7
  • 32537-90-9
  • 52502-68-8
  • 87387-76-6

System Generated Number

  • 0000129497

Molecular Formulas

Molecular Formulas

  • C21-H27-N3-O2.2C4-H4-O4
  • C21-H27-N3-O2.C4-H4-O4

Molecular Formula Fragments

  • C21-H27-N3-O2
  • C4-H4-O4
  • COMPONENT

Structure Descriptors

InChI

InChI=1S/C21H27N3O2.C4H4O4/c1-4-15(12-25)22-21(26)14-8-17-16-6-5-7-18-20(16)13(10-23(18)2)9-19(17)24(3)11-14;5-3(6)1-2-4(7)8/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26);1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,15+,19-;/m1./s1

InChIKey

LWYXFDXUMVEZKS-ZVFOLQIPSA-N

Smiles

CC[C@@H](CO)NC(=O)[C@H]1CN(C)[C@@H]2Cc3cn(C)c4cccc(C2=C1)c34.OC(=O)\C=C/C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 185mg/kg (185mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 101, 1972.
mouse LD50 oral 581mg/kg (581mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 101, 1972.
rabbit LD50 intravenous 28mg/kg (28mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 101, 1972.
rat LD50 intravenous 125mg/kg (125mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 101, 1972.
rat LD50 oral 200mg/kg (200mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 101, 1972.