3,7-Diazabicyclane: a new narcotic analgesic.
The synthesis of a series of 9-phenyl-3,7-diazabicyclanes and 9-(m-hydroxyphenyl)-3,7-diazabicyclanes is described. Members of both series were tested for antinociception in rat tail withdrawal and mouse acetic acid writhing assays. Their affinities for opiate receptors in rat brain homogenate were also determined. The 9-phenyl compounds, 1a-c, were inactive. However, the 9-(m-hydroxyphenyl) analogues, 2a-c, were found to possess significant activity in the writhing assay, comparable to that of morphine. All activity was reversed by naloxone.
D000701:Analgesics, Opioid / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D051379:Mice; D051381:Rats; D011957:Receptors, Opioid / Q000187:drug effects; D013329:Structure-Activity Relationship
D000701:Analgesics, Opioid; D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds; D011957:Receptors, Opioid