Methadone conformation and opioid activity

William L. Duax, G. David Smith, Jane F. Griffin, P. S. Portoghese

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

The inactive methadone analog threo-5-methylmethadone has a solid-state conformation in which the nitrogen is antiperiplanar to the tertiary carbon C(4). Since threo-5-methylmethadone exhibits no opioid agonism either in vivo or in vitro, methadone analogs probably do not have this conformation when bound to an opioid receptor. The potent agonist (-)-erythro-5-methylmethadone has a solid-state conformation in which the nitrogen atom is rotated back toward the phenyl rings on the quarternary carbon, suggesting that this unusual conformation is the active one.

Original languageEnglish (US)
Pages (from-to)417-418
Number of pages2
JournalScience
Volume220
Issue number4595
DOIs
StatePublished - Jan 1 1983

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    Duax, W. L., Smith, G. D., Griffin, J. F., & Portoghese, P. S. (1983). Methadone conformation and opioid activity. Science, 220(4595), 417-418. https://doi.org/10.1126/science.6301007