Methysergide

Methysergide
Clinical data
Trade names	Deseril, Sansert
Other names	UML-491; 1-Methylmethylergonovine; N-[(2S)-1-Hydroxybutan-2-yl]-1,6-dimethyl-9,10-didehydroergoline-8α-carboxamide; N-(1-(Hydroxymethyl)propyl)-1-methyl-D-lysergamide
AHFS/Drugs.com	International Drug Names
MedlinePlus	a603022
Pregnancy; category	AU: C; ;
Routes of; administration	Oral
Drug class	Monoamine receptor modulator; Antimigraine agent
ATC code	N02CA04 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Identifiers
	IUPAC name (6aR,9R)-N-[(2S)-1-Hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide;
CAS Number	361-37-5 ;
PubChem CID	9681;
IUPHAR/BPS	134;
DrugBank	DB00247 ;
ChemSpider	9300 ;
UNII	XZA9HY6Z98;
KEGG	D02357 ;
ChEMBL	ChEMBL1065 ;
CompTox Dashboard (EPA)	DTXSID2023307 ;
ECHA InfoCard	100.006.041
Chemical and physical data
Formula	C21H27N3O2
Molar mass	353.466 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N[C@@H](CC)CO)[C@@H]3/C=C2/c4cccc1c4c(cn1C)C[C@H]2N(C3)C;
	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/s1 ; Key:KPJZHOPZRAFDTN-ZRGWGRIASA-N ;
	(verify)

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 It has been withdrawn from the market in the United States and Canada due to safety concerns.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 10 times 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.

Methysergide was first described in the literature by 1958. It is no longer recommended as a first-line therapy for migraines or cluster headaches. This is due to toxicity, such as cardiac valvulopathy, which was first reported with long-term use in the late 1960s. Ergot-based medications like methysergide fell out of favor for treatment of migraine with the introduction of the triptans in the 1980s.