Methylergonovine

Methylergometrine

Clinical data
Trade names	Methergine
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
Biological half-life	30–120 min
Excretion	Mostly bile
Identifiers
IUPAC name 9,10-Didehydro-N-[1-(hydroxymethyl)-propyl]-D-lysergamide
Synonyms	Methylergobasine Methylergobrevin Methylergonovine
CAS Number	113-42-8 Y
PubChem CID	8226
IUPHAR/BPS	150
ChemSpider	7933 N
UNII	W53L6FE61V
ChEMBL	CHEMBL1201356 N
ECHA InfoCard	100.003.661
Chemical and physical data
Formula	C20H25N3O2
Molar mass	339.432 g/mol
3D model (Jmol)	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 N Key:UNBRKDKAWYKMIV-QWQRMKEZSA-N N
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Methylergometrine (also called methylergonovine, methylergobasin, and D-lysergic acid 1-butanolamide) is a synthetic analogue of ergonovine, a psychedelic alkaloid found in ergot, and many species of morning glory. It is a member of the ergoline family and chemically similar to LSD, ergine, ergometrine, and lysergic acid. Due to its properties, it has a medical use in obstetrics. According to Jonathan Ott, methylergonovine has LSD-like actions above 2 milligrams, due to its agonistic action at the 5HT_2A-mGlu2 receptor protomers. Clinical efficacy occurs around 200 µg, ten times lower than the hallucinogenic threshold.

Methylergometrine maleate is marketed under the trade name Methergine.

Methylergometrine is a smooth muscle constrictor that mostly acts on the uterus. It is most commonly used to prevent or control excessive bleeding following childbirth and spontaneous or elective abortion, and also to aid in expulsion of retained products of conception after a missed abortion (miscarriage in which all or part of the fetus remains in the uterus) and to help deliver the placenta after childbirth. It is available as tablets or injection (IM or IV) or in liquid form to be taken orally.