ContaminantDB: Methysergide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (11)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:23 UTC

Update Date

2026-03-26 19:46:33 UTC

Accession Number

CHEM002152

Identification

Common Name

Methysergide

Class

Small Molecule

Description

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.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Drug
Metabolite
Organic Compound
Serotonin Antagonist
Sympatholytic
Synthetic Compound
Vasoconstrictor Agent

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8beta-carboxamide	ChEBI
(+)-N-(1-(Hydroxymethyl)propyl)-1-methyl-D-lysergamide	ChEBI
1-Methyl-D-lysergic acid butanolamide	ChEBI
1-Methyl-dextro-lysergic acid (+)-1-hydroxy-2-butylamide	ChEBI
1-Methyllysergic acid butanolamide	ChEBI
1-Methylmethylergonovine	ChEBI
9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8-carboxamide	ChEBI
Methysergidum	ChEBI
Metisergida	ChEBI
N-(1-(Hydroxymethyl)propyl)-1-methyl-dextro-(+)-lysergamide	ChEBI
(+)-9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8b-carboxamide	Generator
(+)-9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8β-carboxamide	Generator
1-Methyl-D-lysergate butanolamide	Generator
1-Methyl-dextro-lysergate (+)-1-hydroxy-2-butylamide	Generator
1-Methyllysergate butanolamide	Generator
Methyllysergic acid butanolamide	HMDB
Methysergid	HMDB
Metisergide	HMDB
N-(alpha-(Hydroxymethyl)propyl)-1-methyl-dextro-lysergamide	HMDB
1-Methyllysergic acid butanolamide tartrate, (R-(r,r))-(8beta)-isomer	HMDB

Chemical Formula

C₂₁H₂₇N₃O₂

Average Molecular Mass

353.458 g/mol

Monoisotopic Mass

353.210 g/mol

CAS Registry Number

361-37-5

IUPAC Name

(4R,7R)-N-(1-hydroxybutan-2-yl)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide

Traditional Name

methysergide

SMILES

[H][C@@]12CC3=CN(C)C4=C3C(=CC=C4)C1=C[C@H](CN2C)C(=O)NC(CC)CO

InChI Identifier

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

InChI Key

KPJZHOPZRAFDTN-NQUBZZJWSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Lysergic acids and derivatives

Direct Parent

Lysergamides

Alternative Parents

Substituents

Lysergic acid amide
Indoloquinoline
Benzoquinoline
Pyrroloquinoline
Quinoline-3-carboxamide
N-alkylindole
Quinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
Benzenoid
N-methylpyrrole
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Carboxamide group
Amino acid or derivatives
Tertiary amine
Secondary carboxylic acid amide
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:584020 )
ergot alkaloid (CHEBI:584020 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	195°C
Boiling Point	Not Available
Solubility	2.24e-01 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	2.22	ALOGPS
logP	1.82	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	15.01	ChemAxon
pKa (Strongest Basic)	7.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.5 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.47 m³·mol⁻¹	ChemAxon
Polarizability	40.41 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-4495000000-d0cc0e065ac2a249f139	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-03di-3390100000-c2e2183c67e221dc8c1d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-1009000000-633c43ec26d6039658e4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-5095000000-47b5108f6a3ebd949236	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0c0c-3390000000-7d1562a443e084f1ea99	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-9ba72bc3d8d89f6a4388	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ff9-2059000000-819b11151769bcbb6445	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05g3-6090000000-5d7ac6f788f61ce26929	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0019000000-5a70e47475b13679f8e3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-0059000000-d42a975e818a2288348e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0090000000-22d20459936ae0d0b518	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-c66b7fea4f08e0ca5b51	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1019000000-b7eebee23bde51802f58	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kfx-6193000000-c592c6e25521a17d4740	Spectrum

Toxicity Profile

Route of Exposure

Ingestion (4), rapid.

Mechanism of Toxicity

Ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. This can result in a number of different effects, including vasoconstriction, convulsions, and hallucinations. Methysergide as a serotonin antagonists acts on central nervous system, which directly stimulates the smooth muscle leading to vasoconstriction. Some alpha-adrenergic blocking activity has also been reported. Suggestions have been made by investigators as to the mechanism whereby Methysergide produces its clinical effects, but this has not been finally established, although it may be related to the antiserotonin effect. (1, 3, 4, 5)

Metabolism

Methysergide is metabolized in the liver. (1)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Methysergide is a synthetic derivative of the ergoline family, which occur naturally in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi like other ergoline alkaloids. Methysergide antagonizes the effects of serotonin in blood vessels and gastrointestinal smooth muscle, but has few of the properties of other ergot alkaloids. It is used prophylactically in migraine and other vascular headaches and to antagonize serotonin in the carcinoid syndrome and is sold under the brand names Sansert and Deseril in 2mg dosages. (8, 11)

Minimum Risk Level

Not Available

Health Effects

Ingestion of ergoline alkaloids is known to cause the disease ergotism. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. (2)

Symptoms

Few cases of acute methysergide intoxication have been reported. The possible symptom complex is therefore not fully known. The following symptoms are based on these few case reports. Euphoria, hyperactivity, tachycardia, dilated pupils, and dizziness have been reported in a child with a dose of 20-24 mg of methysergide. In adults, peripheral vasospasm, with diminished or absent pulses, coldness, mottling and cyanosis, has been observed at a dose of 200 mg. Ischemic tissue damage has not been reported in acute overdosage with methysergide.

Treatment

Treatment for overdose consists of removal of the offending drug by induction of emesis, or gastric lavage in the case of very recent intake, repeat dose administration of activated charcoal and catharsis. I.V. fluids may be given as a general supportive measure. Treatment of peripheral vasospasm should consist of warmth, but not heat, and protection of the ischemic limbs. (7)

Concentrations

Not Available

External Links

DrugBank ID

DB00247

HMDB ID

HMDB0014392

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID