Methylergometrine

Methylergometrine
Systematic (IUPAC) name
	9,10-didehydro- N-[1-(hydroxymethyl)- propyl]- D-lysergamide
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a601077
Pregnancy cat.	C (US)
Legal status	℞ Prescription only
Pharmacokinetic data
Metabolism	liver
Half-life	30-120 min
Identifiers
CAS number	113-42-8
ATC code	G02AB01
PubChem	CID 8226
UNII	W53L6FE61V
ChEMBL	CHEMBL1201356
Synonyms	Methylergobasine; Methylergobrevin; Methylergonovine
Chemical data
Formula	C20H25N3O2
Mol. mass	339.432 g/mol
SMILES	eMolecules & PubChem
Physical data
Melt. point	172 °C (342 °F)
Solubility in water	insoluble mg/mL (20 °C)
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Methylergometrine (other names include methylergonovine, methylergobasin, methergine, 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 oxytocic properties, it has a medical use in obstetrics. According to Jonathan Ott, methylergonovine has LSD-like actions above 2 milligrams^{citation needed}. Clinical dosages are ten times lower.

Methylergometrine maleate is marketed under the trade name Methergine.

Obstetric use

Methylergometrine is a blood vessel constrictor and smooth muscle agonist most commonly used to prevent or control excessive bleeding following childbirth and spontaneous or elective abortion. It also causes uterine contractions 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.

Migraine

Methylergometrine is sometimes used for both prevention¹ and acute treatment² of migraine. It is an active metabolite of methysergide.

Side effects

Cholinergic effects such as nausea, vomiting, and diarrhea
Cramping
Dizziness
Pulmonary hypertension
Coronary artery vasoconstriction
Severe systemic hypertension (especially in patients with preeclampsia)
Convulsions

Contraindications

Hypertension
Pregnancy

References

^ Koehler, PJ; Tfelt-Hansen PC (Nov 2008). "History of methysergide in migraine.". Cephalalgia 28 (11). doi:10.1111/j.1468-2982.2008.01648.x. PMID 18644039. http://www.ncbi.nlm.nih.gov/pubmed/18644039. Retrieved 11 December 2011.
^ Niño-Maldonado, Alfredo; Gary Caballero-García, Wilfrido Mercado-Bochero, Fernando Rico-Villademoros, Elena P Calandre (8). "Efficacy and tolerability of intravenous methylergonovine in migraine female patients attending the emergency department: a pilot open-label study". Head Face Med 5 (21). doi:10.1186/1746-160X-5-21. PMC 2780385. PMID 19895705. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2780385.

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[0] Koehler, PJ; Tfelt-Hansen PC (Nov 2008). "History of methysergide in migraine.". Cephalalgia 28 (11). doi:10.1111/j.1468-2982.2008.01648.x. PMID 18644039. http://www.ncbi.nlm.nih.gov/pubmed/18644039. Retrieved 11 December 2011.

[1] Niño-Maldonado, Alfredo; Gary Caballero-García, Wilfrido Mercado-Bochero, Fernando Rico-Villademoros, Elena P Calandre (8). "Efficacy and tolerability of intravenous methylergonovine in migraine female patients attending the emergency department: a pilot open-label study". Head Face Med 5 (21). doi:10.1186/1746-160X-5-21. PMC 2780385. PMID 19895705. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2780385.

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