N-(2-Cyanoethyl) derivatives of meperidine, ketobemidone, and a potent 6,7-benzomorphan.
The N-(2-cyanoethyl)-9alpha-ethyl-5-methyl-6,7-benzomorphan (1c) is a more potent antinociceptive and has stronger receptor binding affinity than its N-methyl analogue 1b. The N-(2-cyanoethyl)-4-phenylpiperidine compounds 2b and 3b were almost inactive compared to their N-methyl congeners 2a and 3a, respectively. It appears that the pharmacological effect of the N-(2-cyanoethyl) moiety is dependent on the opioid on which it is substituted.
D000700:Analgesics / Q000138:chemical synthesis* / Q000378:metabolism; D000818:Animals; D001575:Benzomorphans / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D001667:Binding, Competitive; D001921:Brain / Q000378:metabolism; D004090:Dihydromorphine / Q000378:metabolism; D000882:Haplorhini; D006801:Humans; D066298:In Vitro Techniques; D008253:Macaca mulatta; D008614:Meperidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D051379:Mice; D009019:Morphinans / Q000138:chemical synthesis*; D009021:Morphine Dependence / Q000503:physiopathology; D009570:Nitriles / Q000138:chemical synthesis*; D010880:Piperidines / Q000138:chemical synthesis*; D051381:Rats; D013329:Structure-Activity Relationship
D000700:Analgesics; D001575:Benzomorphans; D009019:Morphinans; D009570:Nitriles; D010880:Piperidines; D008614:Meperidine; D004090:Dihydromorphine