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Substance Name: Methysergide [USAN:INN:BAN]
RN: 361-37-5
UNII: XZA9HY6Z98
InChIKey: KPJZHOPZRAFDTN-ZRGWGRIASA-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 Formula

  • C21-H27-N3-O2

Molecular Weight

  • 353.463
 

Classification Codes

  • Cardiovascular Agents
  • Human Data
  • Neurotransmitter Agents
  • Serotonin Agents
  • Serotonin Antagonists
  • Vasoconstrictor (Specific in Migraine)
  • Vasoconstrictor Agents
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Names and Synonyms

Name of Substance

  • Methysergide
  • Methysergide [USAN:INN:BAN]

MeSH Heading

  • Methysergide

Synonyms

  • (+)-9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8beta-carboxamide
  • (+)-N-(1-(Hydroxymethyl)propyl)-1-methyl-D-lysergamide
  • 1-Methyl-D-lysergic acid butanolamide
  • 1-Methyl-dextro-lysergic acid (+)-1-hydroxy-2-butylamide
  • 1-Methyllysergic acid butanolamide
  • 1-Methylmethylergonovine
  • 9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8-carboxamide
  • BRN 0765985
  • Deseril
  • Desernil
  • Desernyl
  • Deseryl
  • Desril
  • EINECS 206-644-0
  • Ergoline-8-carboxamide, 9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-, (8beta)-
  • Ergoline-8beta-carboxamide, 9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-
  • HSDB 3237
  • Lysergamide, N-(1-(hydroxymethyl)propyl)-1-methyl-, D-
  • Methyllysergic acid butanolamide
  • Methysergid
  • Methysergide
  • Methysergidum
  • Methysergidum [INN-Latin]
  • Metisergide
  • Metisergide [DCIT]
  • Metisergido
  • Metisergido [INN-Spanish]
  • N-(1-(Hydroxymethyl)propyl)-1-methyl-dextro-(+)-lysergamide
  • N-(alpha-(Hydroxymethyl)propyl)-1-methyl-dextro-lysergamide
  • Sansert
  • UML 491
  • UML-491
  • UNII-XZA9HY6Z98

Systematic Names

  • Ergoline-8-beta-carboxamide, 9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-
  • Ergoline-8-carboxamide, 9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-, (8beta)-
  • Methysergide

Registry Numbers

CAS Registry Number

  • 361-37-5

FDA UNII

  • XZA9HY6Z98

Other Registry Numbers

  • 156558-44-0
  • 2016-33-3
  • 29987-97-1
  • 47478-64-8
  • 746-51-0

System Generated Number

  • 0000361375

Structure Descriptors

InChI

1S/C21H27N3O2/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/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26)/t14-,15+,19-/m1/s1

InChIKey

KPJZHOPZRAFDTN-ZRGWGRIASA-N

Smiles

c12c3C=4[C@H]([N@@](C[C@@H](C4)C(N[C@@H](CC)CO)=O)C)Cc1cn(c2ccc3)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 28ug/kg (0.028mg/kg) BEHAVIORAL: HEADACHE

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: ANOREXIA (HUMAN
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 220, 1966.
mouse LD50 intravenous 185mg/kg (185mg/kg)   Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963.
mouse LD50 oral 440mg/kg (440mg/kg)   Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963.
women TDLo oral 17mg/kg/77W-I (17mg/kg) GASTROINTESTINAL: OTHER CHANGES

VASCULAR: OTHER CHANGES
Mayo Clinic Proceedings. Vol. 72, Pg. 1148, 1997.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 195 deg C   EXP
log P (octanol-water) 1.550 (none)   EST
Atmospheric OH Rate Constant 4.16E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.