(exo,exo)-2-Aryltropane-3-carboxylic esters, hypoglycemic agents with accompanying analgesic activity

(exo, exo)-2-Aryltropane-3-carboxylic esters of types 6, 7, and 10 lower circulating blood glucose levels by 60--80%. This activity is accompanied by an analgesic activity roughly equal to that of codeine. Both of these activities reside in the 1R enantiomer and extensive structure-activity studies...

Full description

Saved in:
Bibliographic Details
Published inJournal of medicinal chemistry Vol. 21; no. 12; pp. 1243 - 1253
Main Authors Clarke, Robert L, Heckeler, Monica L, Gambino, Anthony J, Daum, Sol J, Harding, Homer R, Pierson, Anne K, Teiger, David G, Pearl, Jack, Shargel, Leon D, Goehl, Thomas J
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 01.12.1978
Subjects
Administration, Oral
Analgesics, Opioid - chemical synthesis
Animals
Catalepsy - chemically induced
Dealkylation
Dogs
Humans
Hypoglycemic Agents - administration & dosage
Hypoglycemic Agents - chemical synthesis
Injections, Subcutaneous
Male
Mice
Molecular Conformation
Rats
Respiratory Insufficiency - chemically induced
Stereoisomerism
Structure-Activity Relationship
Tropanes - administration & dosage
Tropanes - chemical synthesis
Tropanes - pharmacology
Online AccessGet full text

Cover

More Information
Summary:(exo, exo)-2-Aryltropane-3-carboxylic esters of types 6, 7, and 10 lower circulating blood glucose levels by 60--80%. This activity is accompanied by an analgesic activity roughly equal to that of codeine. Both of these activities reside in the 1R enantiomer and extensive structure-activity studies failed to separate them. The specific opioid antagonist nalorphine blocks the analgesic activity but does not diminish the hypoglycemic action. Conformational integrity afforded by the ethylene bridge is neccessary for the observed activities.
Bibliography:ark:/67375/TPS-T3FVFXVH-D
istex:27C924DF185C2E2599FA9B36AFC5A9BCFBDA6555
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00210a014