Methylergometrine

Methylergometrine
Clinical data
Trade names	Methergine
Other names	Methylergonovine; methylergobasin; Methylergobasine; Methylergobrevin; d-Lysergic acid 1-butanolamide; N-[(2S)-1-Hydroxybutan-2-yl]-6-methyl-9,10-didehydroergoline-8β-carboxamide
AHFS/Drugs.com	International Drug Names
MedlinePlus	a601077
Pregnancy; category	Contraindicated;
Routes of; administration	Oral
ATC code	G02AB01 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Metabolism	Liver
Elimination half-life	30–120 minutes
Excretion	Mostly bile
Identifiers
	IUPAC name (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;
CAS Number	113-42-8 ;
PubChem CID	8226;
IUPHAR/BPS	150;
ChemSpider	7933 ;
UNII	W53L6FE61V;
KEGG	D08207;
ChEMBL	ChEMBL1201356 ;
CompTox Dashboard (EPA)	DTXSID00904978 DTXSID1023283, DTXSID00904978 ;
ECHA InfoCard	100.003.661
Chemical and physical data
Formula	C20H25N3O2
Molar mass	339.439 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	172 °C (342 °F)
Solubility in water	Insoluble mg/mL (20 °C)
	SMILES CC[C@@H](CO)NC(=O)[C@@H]2/C=C1/c3cccc4N\C=C(\C[C@H]1N(C)C2)c34;
	InChI InChI=1S/C20H25N3O2/c1-3-14(11-24)22-20(25)13-7-16-15-5-4-6-17-19(15)12(9-21-17)8-18(16)23(2)10-13/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25)/t13-,14+,18-/m1/s1 ; Key:UNBRKDKAWYKMIV-QWQRMKEZSA-N ;
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Methylergometrine, also known as methylergonovine and sold under the brand name Methergine, is a medication of the ergoline and lysergamide groups which is used as an oxytocic in obstetrics and in the treatment of migraine. It reportedly produces psychedelic effects similar to those of lysergic acid diethylamide (LSD) at high doses.^{[citation needed]}

^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.