Structural Formula Vector Image
Title: Ergot
Additional Names: Secale cornutum; spurred rye
Literature References: Dried sclerotia of the fungus Claviceps purpurea (Fries) Tul., Hypocreaceae, parasitic on rye plants. Habit. Europe; cultivated in Spain, Germany, and France. Four main classes of ergot alkaloids can be distinguished: clavine alkaloids, lysergic acids, lysergic acid amides and ergot peptide alkaloids. There are ten ergot peptide alkaloids which are ergotamine, ergosine, ergocristine, ergocryptine, ergocornine, ergotaminine, ergosinine, ergocristinine, ergocryptinine, and ergocorninine, the last five alkaloids being isomers of the first five. These allkaloids are typified by a structure consisting of lysergic acid, dimethylpyruvic acid, proline, and phenylalanine joined in amide linkages. In 1943 A. Stoll and A. Hofmann, Helv. Chim. Acta 26, 1570 (1943) made it clear that the ergotoxine reported by G. Barger and F. H. Carr, J. Chem. Soc. 91, 377 (1907) and by F. Kraft, Arch. Pharm. 244, 336 (1906) was but a mixture of ergocristine, ergocryptine, and ergocornine, and that the ergotinine, first reported by C. Tanret, Compt. Rend. 81, 891 (1875), was also a mixture consisting of ergocristinine, ergocryptinine, and ergocorninine. Other constituents of ergot are ergonovine, ergometrinine, ergoclavine, elymoclavine, trimethylamine, putrescine, cadaverine, agmatine, histamine, tyramine, histidine, tyrosine, valine, leucine, betaine, choline, acetylcholine, ergothioneine, 15-30% fatty oil, ergosterol, mannitol, lactic acid, and succinic acid. Production of ergocryptinine and elymoclavine by cultures of fungi parasitic on Elymus mollis Trin: Abe et al., US 2835675. Production of ergot alkaloids by saprophytic cultures: Adams, US 3117917 (1964 to Miles Labs.). Ergot alkaloid fermentation: W. J. Kelleher, Adv. Appl. Microbiol. vol. 11, 211 (1969). Biosynthesis of ergot alkaloids: H. G. Floss, Tetrahedron 32, 873 (1976). Reviews: Gröger in Microbial Toxins vol. VIII, S. Kadis et al., Eds. (Academic Press, New York, 1972) pp 321-373; Stadler, Stütz, "The Ergot Alkaloids" in The Alkaloids vol. 15, R. H. F. Manske, Ed. (Academic Press, New York, 1975) pp 1-40. Books: F. J. Bove, The Story of Ergot (Karger, Basel, 1970) 297 pp; Handb. Exp. Pharmacol. 49 entitled "Ergot Alkaloids and Related Compounds", B. Berde, H. O. Schild, Eds. (Springer-Verlag, New York, 1978) 1003 pp.
CAUTION: Potential symptoms of overexposure are CNS stimulation, nausea, vomiting, weakness, tremors, excitement, confusion, convulsions, tachycardia, mydriasis, peripheral vasoconstriction progressing to gangrene. See Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section II, pp 218-219.
Therap-Cat: Vasoconstrictor (specific in migraine).
Therap-Cat-Vet: Has been used as an oxytocic.
Keywords: Antimigraine.

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