N-substituted octahydro-4a-(3-hydroxyphenyl)-10a- methylbenzo[g]isoquinolines are opioid receptor pure antagonists

F. Ivy Carroll; S. Mascarella; Jason P. Burgess; James B. Thomas; James B. Thomas; S. Wayne Mascarella; Jason P. Burgess; Heng Xu; KB McCullough; RB Rothman; JL Flippen-Anderson; CF George; BE Cantrell; DM Zimmerman; Ivy Carroll

N-substituted octahydro-4a-(3-hydroxyphenyl)-10a- methylbenzo[g]isoquinolines are opioid receptor pure antagonists

Thomas, J., Mascarella, S., Burgess, J., Xu, H., McCullough, KB., Rothman, RB., Flippen-Anderson, JL., George, CF., Cantrell, BE., Zimmerman, DM., & 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. https://doi.org/10.1016/S0960-894X(98)00576-9

Copy citation

Abstract

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.