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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
- All
- Classifications
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- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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/s1InChIKey
KPJZHOPZRAFDTN-ZRGWGRIASA-NSmiles
CC[C@@H](CO)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.