Methysergide

Methysergide
Clinical data
Trade names	Desernil, 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; ;
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 of the ergoline and lysergamide groups which is used in the prophylaxis and treatment of migraine and cluster headaches.^[2] It has been withdrawn from the market in the United States and Canada due to adverse effects.^[3] It is taken by mouth.^[3]

Methysergide is no longer recommended as a first line treatment protocol by international headache societies, hospitals, and neurologists in private practice, for migraines or cluster headaches as side effects were first reported with long-term use in the late 1960s, and ergot-based treatments fell out of favor for the treatment of migraines with the introduction of triptans in the 1980s.

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 677–. ISBN 978-3-88763-075-1.
^ ^a ^b Cite error: The named reference pmid23815106 was invoked but never defined (see the help page).

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 677–. ISBN 978-3-88763-075-1.

[pmid23815106-3] Cite error: The named reference pmid23815106 was invoked but never defined (see the help page).

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