ChemFOnt: Showing chemical card for Methysergide (CFc000008785)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:42 UTC

Chemfont ID

CFc000008785

Molecule Identification

Common Name

Methysergide

Definition

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. [PubChem]

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 Weight

353.458

Monoisotopic Molecular Weight

353.210327123

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

CAS Registry Number

361-37-5

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 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014392)

Process

Not Available

Role

Industrial application

Vasoconstrictor agent (HMDB: HMDB0014392)
Serotonergic antagonist (HMDB: HMDB0014392)
Sympatholytic agent (HMDB: HMDB0014392)

Physical Properties

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon