5632. Lysergamide

Nomenclature

CAS number: 478-94-4
9,10-Didehydro-6-methylergoline-8β-carboxamide; lysergic acid amide; ergine.
C16H17N3O; mol wt 267.33.
C 71.89%, H 6.41%, N 15.72%, O 5.98%.

Description and references

Isoln from Rivea corymbosa (L.) and from Ipomoea tricolor Cav., Convolvulaceae: Hofmann, Tscherter, Experientia 16, 414 (1964). Prepn from lysergic acid hydrazide: Ainsworth, US 2756235 (1956 to Lilly); from lysergic acid and phosgene-dimethylformamide complex: Patelli, Bernardi, US 3141887 (1964 to Farmitalia). Microbiological production: Rutschmann, Kobel, US 3219545 (1965 to Sandoz).

Chemical structure

Properties

Prisms from methanol, dec 242°. [α]205461 +15° (c = 0.5 in pyridine).

Derivative

Methanesulfonate.
C16H17N3O.CH3SO3H; mol wt 363.43.
C 56.18%, H 5.82%, N 11.56%, O 17.61%, S 8.82%.

Properties

Prisms from methanol + acetone, dec 232°.

Note

This is a controlled substance (depressant): 21 CFR, 1308.13.