Ergonovine

Title: Ergonovine
CAS Registry Number: 60-79-7
CAS Name: [8b(S)]-9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8-carboxamide
Additional Names: N-[a-(hydroxymethyl)ethyl]-D-lysergamide; D-lysergic acid L-2-propanolamide; ergometrine
Trademarks: Ergobasine; Ergotocine; Ergostetrine; Ergotrate (Lilly); Ergoklinine; Syntometrine
Molecular Formula: C19H23N3O2
Molecular Weight: 325.40
Percent Composition: C 70.13%, H 7.12%, N 12.91%, O 9.83%
Literature References: From some ergots: A. Stoll et al., US 2809920 (1957 to Saul & Co.). Prepn from D-lysergic acid and L(+)-2-amino-1-propanol: A. Stoll, A. Hofmann, Helv. Chim. Acta 26, 944 (1943); Pioch, US 2736728 (1956 to Lilly); Patelli, Bernardi, US 3141887 (1964 to Farmitalia). Structure: A. Stoll et al., Helv. Chim. Acta 34, 1544 (1951). Total synthesis: E. C. Kornfeld et al., J. Am. Chem. Soc. 78, 3087 (1956). Metabolism: Slaytor, Wright, J. Med. Pharm. Chem. 5, 483 (1962). Comprehensive description of the maleate: V. D. Reif, Anal. Profiles Drug Subs. 11, 273-312 (1982). Toxicity data: R. P. Beliles, Toxicol. Appl. Pharmacol. 23, 537 (1972). Clinical use in diagnosis of angina: L. A. DiCarlo, Jr. et al., Am. J. Cardiol. 54, 744 (1984); R. Nordlander, R. Orinius, Acta Med. Scand. 221, 47 (1987).
Properties: Tetrahedra from ethyl acetate, fine needles from benzene. Tends to form solvated crystals, mp 162°. [a]D20 +90° (in water). pK 6.8. Freely sol in lower alcohols, ethyl acetate, acetone; more sol in water than the other principal alkaloids of ergot; slightly sol in chloroform.
Melting point: mp 162°
pKa: pK 6.8
Optical Rotation: [a]D20 +90° (in water)
Derivative Type: Hydrochloride
Molecular Formula: C19H23N3O2.HCl
Molecular Weight: 361.87
Percent Composition: C 63.06%, H 6.68%, N 11.61%, O 8.84%, Cl 9.80%
Properties: Needles from ethyl alcohol, dec 246°. [a]D25 +63° (c = 0.9). More sol in water than the hydrobromide.
Optical Rotation: [a]D25 +63° (c = 0.9)
Derivative Type: Maleate
CAS Registry Number: 129-51-1
Trademarks: Cornocentin; Ergotrate Maleate (Lilly); Ermetrine (Organon)
Molecular Formula: C19H23N3O2.C4H4O4
Molecular Weight: 441.48
Percent Composition: C 62.57%, H 6.16%, N 9.52%, O 21.74%
Properties: Crystals, dec 167°. [a]D25 +48 to +57°. One gram dissolves in 36 ml water, 120 ml alcohol. Nearly insol in ether and chloroform. LD50 i.v. in mice: 8.26 mg/kg (Beliles).
Optical Rotation: [a]D25 +48 to +57°
Toxicity data: LD50 i.v. in mice: 8.26 mg/kg (Beliles)
Derivative Type: Tartrate hydrate
Trademarks: Basergin; Neofemergen
Molecular Formula: (C19H23N3O2)2.C4H6O6.H2O
Molecular Weight: 818.91
Percent Composition: C 61.60%, H 6.65%, N 10.26%, O 21.49%
Properties: Crystals, slightly sol in water.
Derivative Type: Hydracrylate
Trademarks: Ergotrate-H (Lilly)
Molecular Formula: C41H52N6O7
Molecular Weight: 740.89
Percent Composition: C 66.47%, H 7.07%, N 11.34%, O 15.12%
Therap-Cat: Oxytocic.
Therap-Cat-Vet: Oxytocic.
Keywords: Oxytocic.
Ergosine Ergostane Ergostanol Ergosterol Ergotamine

Ergometrine
Ergonovine-skeletal.svg
Systematic (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
Clinical data
AHFS/Drugs.com monograph
Pregnancy cat. X
Legal status List I precursor (US)
Routes Oral
Pharmacokinetic data
Metabolism hepatic
Excretion renal
Identifiers
CAS number 60-79-7 YesY
ATC code G02AB03
PubChem CID 443884
DrugBank DB01253
ChemSpider 391970 YesY
UNII WH41D8433D YesY
KEGG D07905 YesY
ChEBI CHEBI:4822 YesY
ChEMBL CHEMBL119443 YesY
Synonyms Ergonovine, lysergic acid beta- propanolamide
Chemical data
Formula C19H23N3O2 
Mol. mass 325.41 g/mol
 YesY (what is this?)  (verify)

Ergometrine (other names include ergonovine and d-lysergic acid beta-propanolamide), is an ergoline (and lysergamide) derivative, and one of the primary ergot and morning glory alkaloids . It is chemically similar to lysergic acid diethylamide (LSD), ergine, and lysergic acid.