3655. Ergonovine

Nomenclature

CAS number: 60-79-7
[8β(S)]-9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8-carboxamide; N-[α-(hydroxymethyl)ethyl]-d-lysergamide; d-lysergic acid l-2-propanolamide; ergometrine; Ergobasine; Ergotocine; Ergostetrine; Ergotrate (Lilly); Ergoklinine; Syntometrine.
C19H23N3O2; mol wt 325.40.
C 70.13%, H 7.12%, N 12.91%, O 9.83%.

Description and 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).

Chemical structure

Properties

Tetrahedra from ethyl acetate, fine needles from benzene. Tends to form solvated crystals, mp 162°. [α]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.

Derivative

Hydrochloride.
C19H23N3O2.HCl; mol wt 361.87.
C 63.06%, H 6.68%, N 11.61%, O 8.84%, Cl 9.80%.

Properties

Needles from ethyl alcohol, dec 246°. [α]D25 +63° (c = 0.9). More sol in water than the hydrobromide.

Derivative

Maleate.

Nomenclature

CAS number: 129-51-1
Cornocentin; Ergotrate Maleate (Lilly); Ermetrine (Organon).
C19H23N3O2.C4H4O4; mol wt 441.48.
C 62.57%, H 6.16%, N 9.52%, O 21.74%.

Properties

Crystals, dec 167°. [α]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).

Derivative

Tartrate hydrate.

Nomenclature

Basergin; Neofemergen.
(C19H23N3O2)2.C4H6O6.H2O; mol wt 818.91.
C 61.60%, H 6.65%, N 10.26%, O 21.49%.

Properties

Crystals, slightly sol in water.

Derivative

Hydracrylate.

Nomenclature

Ergotrate-H (Lilly).
C41H52N6O7; mol wt 740.89.
C 66.47%, H 7.07%, N 11.34%, O 15.12%.

Therapeutic Category

Oxytocic.

Therapeutic Category (Veterinary)

Oxytocic.

Keywords

Oxytocic