Structure via PubChem · Public domain (PubChem)
methysergide
Sign in to saveAlso known as 1-methylmethylergonovine, Deseril®, Sansert®, UML-491
Methysergide, sold under the brand names Deseril and Sansert, is a monoaminergic medication which is used in the prevention and treatment of migraine and cluster headaches. It has been withdrawn from the market in the United States and Canada due to safety concerns. The drug has also been found to produce psychedelic effects at high doses. It is taken orally.
Chemical data
- Formula
- C21H27N3O2
- Molecular weight
- 353.5 g/mol
- IUPAC name
- (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide
- SMILES
- CC[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2CC3=CN(C4=CC=CC(=C34)C2=C1)C)C
- InChIKey
- KPJZHOPZRAFDTN-ZRGWGRIASA-N
- XLogP
- 2.3
- Polar surface area
- 57.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1962
- Admin. routes
- oral
- Indications
- migraine disorder
via ChEMBL · EBI
Research
4,681 papers- Methysergide.Cephalalgia : an international journal of headache · 1998
- History of methysergide in migraine.Cephalalgia : an international journal of headache · 2008
- METHYSERGIDE.British medical journal · 1964
- Methysergide.The Practitioner · 1967
- [Methysergide].Pharmaceutisch weekblad · 1967
via PubMed
Wikidata facts
- Mass
- 353.21
- Has use
- medication
Show 6 more facts
- defined daily dose
- 4
- chemical formula
- C₂₁H₂₇N₃O₂
- subject has role
- serotonin antagonist
- isomeric SMILES
- CC[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2CC3=CN(C4=CC=CC(=C34)C2=C1)C)C
- canonical SMILES
- CCC(CO)NC(=O)C1CN(C2CC3=CN(C4=CC=CC(=C34)C2=C1)C)C
- Commons category
- Methysergide
via Wikidata · CC0
~13 min read
Encyclopedic overview
21 sectionsContents
- Medical uses
- Migraine and cluster headaches
- Other uses
- Side effects
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- Analogues
- Natural occurrence
- History
- Society and culture
- Recreational use
- Controversy
- Legal status
- Canada
- United States
- See also
- References
- External links
Methysergide, sold under the brand names Deseril and Sansert, is a monoaminergic medication which is used in the prevention and treatment of migraine and cluster headaches. It has been withdrawn from the market in the United States and Canada due to safety concerns. The drug has also been found to produce psychedelic effects at high doses. It is taken orally.
The drug is a prodrug of methylergometrine (methylergonovine), which circulates at levels about 10times higher than those of methysergide. Whereas methysergide is a mixed agonist of some serotonin receptors (e.g., the serotonin 5-HT1 receptors) and antagonist of other serotonin receptors (e.g., the serotonin 5-HT2 receptors), methylergonovine is a non-selective agonist of most of the serotonin receptors, including of both the serotonin 5-HT1 and 5-HT2 receptor subgroups. Methysergide and methylergometrine are ergolines and lysergamides and are related to the ergot alkaloids.
Excerpted from Wikipedia’s “methysergide” article, available under the CC BY-SA 4.0 licence.