Ergonovine

Ergonovine
Clinical data
Trade names	Ergotrate, Ergotrate Maleate
Other names	Ergometrine; Ergobasin; Ergotocine; Ergostetrine; Lysergic acid propanolamide; Lysergic acid hydroxymethylethylamide; ᴅ-Lysergic acid-1,2-propanolamide; ᴅ-Lysergic acid 1-(hydroxymethyl)ethylamide; ᴅ(+)-Lysergic acid-β-hydroxyisopropylamide
AHFS/Drugs.com	Monograph
Routes of; administration	oral, intramuscular, intravenous
Drug class	Serotonin receptor agonists; Uterotonic
ATC code	G02AB03 (WHO) ;
Legal status
Legal status	BR: Class D1 (Drug precursors); CA: Schedule VI; US: ℞-only;
Pharmacokinetic data
Metabolism	Liver (partly CYP3A4)
Elimination half-life	2-phase (10 min; 2 hrs)
Excretion	Bile duct
Identifiers
	IUPAC name (6aR,9R)-N-((S)-1-Hydroxypropan- 2-yl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide;
CAS Number	60-79-7 ;
PubChem CID	443884;
IUPHAR/BPS	148;
DrugBank	DB01253 ;
ChemSpider	391970 ;
UNII	WH41D8433D;
KEGG	D07905 ;
ChEBI	CHEBI:4822 ;
ChEMBL	ChEMBL119443 ;
CompTox Dashboard (EPA)	DTXSID8046323 ;
ECHA InfoCard	100.000.441
Chemical and physical data
Formula	C19H23N3O2
Molar mass	325.412 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [H][C@@]12Cc3c[nH]c4cccc(C1=C[C@@H](C(=O)N[C@@H](C)CO)CN2C)c34;
	InChI InChI=1S/C19H23N3O2/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/t11-,13+,17+/m0/s1 ; Key:WVVSZNPYNCNODU-XTQGRXLLSA-N ;
	(verify)

Ergonovine, also known as ergometrine and lysergic acid propanolamide, is a medication used to cause contractions of the uterus to treat heavy vaginal bleeding after childbirth. It can be used either by mouth, by injection into a muscle, or injection into a vein.

Ergonovine was discovered in 1932. It is on the World Health Organization's List of Essential Medicines. Ergonovine is controlled in some countries because it can be used to make the psychedelic drug lysergic acid diethylamide (LSD). It is also known to produce psychedelic effects itself at high doses.