6-substituted 1,3,4,5-tetrahydrobenz[cd]indol-4-amines: potent serotonin agonists.
A series of 6-substituted tricyclic ergoline partial structures has been synthesized and found to possess very strong serotonin agonist activity. A methoxy group at the 6-position greatly enhances activity, but at the expense of compound stability. Substituting the 6-position with protophyllic groups that are also electron-withdrawing in character enhances both activity and stability.
Flaugh
M E
ME
Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285.
Mullen
D L
DL
Fuller
R W
RW
Mason
N R
NR
D000818:Animals; D001921:Brain / Q000187:drug effects / Q000378:metabolism; D055598:Chemical Phenomena; D002621:Chemistry; D003345:Corticosterone / Q000097:blood; D006897:Hydroxyindoleacetic Acid / Q000378:metabolism; D007211:Indoles / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology*; D008297:Male; D051381:Rats; D011919:Rats, Inbred Strains; D011985:Receptors, Serotonin / Q000187:drug effects* / Q000378:metabolism; D012701:Serotonin / Q000378:metabolism; D013329:Structure-Activity Relationship
D007211:Indoles; D011985:Receptors, Serotonin; D012701:Serotonin; D006897:Hydroxyindoleacetic Acid; D003345:Corticosterone