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;
DrugBank	DB00353;
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 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.^[1] Previously thought to be an exclusively synthetic compound, it has been reported to occur naturally in Argyreia nervosa (Hawaiian baby woodrose).^[2]^[3] The drug is on the World Health Organization's List of Essential Medicines.^[4]

^ Ott J, Neely P (April 1980). "Entheogenic (hallucinogenic) effects of methylergonovine". Journal of Psychedelic Drugs. 12 (2): 165–166. doi:10.1080/02791072.1980.10471568. PMID 7420432.
^ Chen W, De Wit-Bos L (2020). Risk assessment of Argyreia nervosa (PDF) (Report). doi:10.21945/rivm-2019-0210.
^ Paulke A, Kremer C, Wunder C, Wurglics M, Schubert-Zsilavecz M, Toennes SW (April 2015). "Studies on the alkaloid composition of the Hawaiian Baby Woodrose Argyreia nervosa, a common legal high". Forensic Sci Int. 249: 281–293. doi:10.1016/j.forsciint.2015.02.011. PMID 25747328.
^ 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.