Structure via PubChem · Public domain (PubChem)
methylergonovine
Sign in to saveAlso known as methylergobasin, D-lysergic acid 1-butanolamide, MET827, methylergometrin, methylergometrine, 9,10-didehydro-N-[1-(hydroxymethyl)-propyl]-D-lysergamide
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 as an antimigraine agent in the treatment of migraine headaches. It reportedly produces psychedelic effects similar to those of lysergic acid diethylamide (LSD) at high doses.
Chemical data
- Formula
- C20H25N3O2
- Molecular weight
- 339.4 g/mol
- 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
- SMILES
- CC[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
- InChIKey
- UNBRKDKAWYKMIV-QWQRMKEZSA-N
- XLogP
- 2.3
- Polar surface area
- 68.4 Ų
- H-bond donors
- 3
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1946
- Admin. routes
- oral, parenteral
via ChEMBL · EBI
Research
588 papers- Uterotonic Medications: Oxytocin, Methylergonovine, Carboprost, Misoprostol.Anesthesiology clinics · 2017
- Preventing postpartum hemorrhage with combined therapy rather than oxytocin alone.American journal of obstetrics & gynecology MFM · 2023
- Inadvertent Methylergonovine administration to a newborn.The American journal of emergency medicine · 2021
- Methylergonovine maleate as a cluster headache prophylactic: a study and review.Headache · 1997
- Methylergonovine maleate and the risk of myocardial ischemia and infarction.American journal of obstetrics and gynecology · 2013
via PubMed
Wikidata facts
- Mass
- 339.195
- Has use
- medication
Show 6 more facts
- significant drug interaction
- saquinavir
- chemical formula
- C₂₀H₂₅N₃O₂
- World Health Organisation international non-proprietary name
- methylergometrine
- isomeric SMILES
- CC[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
- canonical SMILES
- CCC(CO)NC(=O)C1CN(C2CC3=CNC4=CC=CC(=C34)C2=C1)C
- defined daily dose
- 0.2
via Wikidata · CC0
~6 min read
Encyclopedic overview
20 sectionsContents
- Medical uses
- Obstetric use
- Migraine
- Contraindications
- Side effects
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Natural occurrence
- Chemistry
- History
- Society and culture
- Recreational use
- Legal status
- Canada
- United States
- See also
- References
- External links
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 as an antimigraine agent in the treatment of migraine headaches. It reportedly produces psychedelic effects similar to those of lysergic acid diethylamide (LSD) at high doses.
==Medical uses== ===Obstetric use=== 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.
Excerpted from Wikipedia’s “methylergonovine” article, available under the CC BY-SA 4.0 licence.