N-substituted octahydro-4a-(3-hydroxyphenyl)-10a- methylbenzo[g]isoquinolines are opioid receptor pure antagonists
Thomas, J., Mascarella, S., Burgess, J., Xu, H., McCullough, K. B., Rothman, R. B., ... Carroll, F. (1998). N-substituted octahydro-4a-(3-hydroxyphenyl)-10a- methylbenzo[g]isoquinolines are opioid receptor pure antagonists. Bioorganic and Medicinal Chemistry Letters, 8(22), 3149-3152. DOI: 10.1016/S0960-894X(98)00576-9
N-Methyl- and N-phenylethyl-(±)-1,2,3,4,4a,5,10,10a-octahydro-4a-(3-hydroxyphenyl)-10a-methyl-benzo[g]isoquinolines (4 and 5, respectively) were found to be pure opioid antagonists. These compounds were shown to share many of the characteristics identified with the N-methyl- and N-phenylethyl trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine (1 and 2, respectively) including N-substituent mediated potency and a lack of N-substituent mediated antagonism. These data suggest that compounds 4 and 5 and the N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines (1 and 2) may interact with opioid receptors similarly.