3662. Ergotaminine

Nomenclature

CAS number: 639-81-6
12′-Hydroxy-2′-methyl-5′α-(phenylmethyl)-8α-ergotaman-3′,6′,18-trione.
C33H35N5O5; mol wt 581.66.
C 68.14%, H 6.07%, N 12.04%, O 13.75%.

Description and references

An alkaloid isomeric with ergotamine, q.v. Isoln from ergot: Stoll, Helv. Chim. Acta 28, 1283 (1945); Stoll et al., US 2809920 (1957 to Saul & Co.); Tabor, Vining, Can. J. Microbiol. 3, 55 (1957).

Properties

Crystallizes solvent-free, unlike ergotamine which tends to retain the solvent of crystn. Thin rhombic plates from methanol, dec 241-243°. [α]D20 +369° (c = 0.5 in chloroform). Much less sol than ergotamine; sol in about 1000 parts boiling alcohol, 1500 parts boiling methanol; fairly sol in chloroform, pyridine, glacial acetic acid. Does not seem to form salts.