title: 14 beta-(2-bromoacetamido)morphine and 14 beta-(2-bromoacetamido)morphinone.
abstract: 14 beta-(2-Bromoacetamido)morphine (6) and 14 beta-(2-bromoacetamido)morphinone (9) were prepared preferably from the adduct of thebaine and 1-chloro-1-nitrosocyclohexane, which on reduction in methanol solution gave 14-aminocodeinone (2) and the corresponding ketal (3). When tested in a receptor-binding assay, the IC50 values of 6 and 9 were 15 and 10 nM, respectively. If the incubation time during the assay was increased from 15 to 30 min, irreversible binding of both ligands was observed.
mesh_terms: D000818:Animals; D002846:Chromatography, Affinity / Q000379:methods; D009022:Morphine Derivatives / Q000138:chemical synthesis* / Q000378:metabolism; D051381:Rats; D011957:Receptors, Opioid / Q000378:metabolism*
chemical_list: D009022:Morphine Derivatives; D011957:Receptors, Opioid; C030452:14 beta-bromoacetamidomorphine; C039840:14-(2-bromoacetamido)morphinone