1423. Bromolysergide

Nomenclature

CAS number: 478-84-2
(8β)-2-Bromo-9,10-didehydro-N,N-diethyl-6-methylergoline-8-carboxamide; d-2-bromolysergic acid diethylamide; 2-bromo-N,N-diethyl-d-lysergamide; bromo-LSD; BOL-148.
C20H24BrN3O; mol wt 402.33.
C 59.71%, H 6.01%, Br 19.86%, N 10.44%, O 3.98%.

Description and references

Prepd by bromination of lysergide, q.v.: Troxler, Hofmann, Helv. Chim. Acta 40, 2160 (1957). Serotonin antagonist without the hallucinogenic activity of LSD: J. P. Bennett, S. H. Snyder, Brain Res. 94, 523 (1975).

Chemical structure

Properties

Needles from ether, mp 120-127°. [α]D20 +15° (c = 0.5 in pyridine); [α]D20 +53° (c = 0.5 in chloroform). uv max: 240, 301 nm (log ε 4.28, 3.95).