PMID: 7932569Sep 30, 1994Paper

Antipodal alpha-N-(methyl through decyl)-N-normetazocines (5,9 alpha-dimethyl-2'-hydroxy-6,7-benzomorphans): in vitro and in vivo properties

Journal of Medicinal Chemistry
E L MayArthur E Jacobson

Abstract

The enantiomeric (-)- and (+)-N-(methyl through decyl) normetazocines (5,9 alpha-dimethyl-2'-hydroxy-6,7-benzomorphans) were synthesized and their in vitro and in vivo activities determined. Increasingly bulky enantiomeric N-alkyl homologs were prepared until their interaction with the sigma 1 receptor decreased and their insolubility became a hindrance to their evaluation in vivo and/or in vitro. The (-)-methyl, -pentyl, -hexyl, and -heptyl homologs were essentially as potent as, or more potent than, morphine in the tail-flick, phenylquinone, and hot-plate assays for antinociceptive activity; the (-)-propyl homolog had narcotic antagonist activity between that of nalorphine and naloxone in the tail-flick vs morphine assay, and it also displayed antagonist properties in the single-dose suppression assay in the rhesus monkey. The antinociceptively potent (-)-heptyl homolog did not substitute for morphine in monkeys but did show morphine-like properties in a primary physical-dependence study in continuously infused rats. All five potent compounds showed high affinity for the mu opioid receptor from both rat and monkey preparations and the kappa opioid receptor (< 0.05 microM), and all except the (-)-methyl homolog interacted reas...Continue Reading

Citations

Oct 1, 1996·Drug and Alcohol Dependence·M D ActeoW L Woolverton
Jun 10, 2015·Journal of Receptor and Signal Transduction Research·Colin G Rousseaux, Stephanie F Greene
Jun 10, 2015·Organic & Biomolecular Chemistry·Matthias P QuickBernhard Wünsch
Mar 17, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Rita TurnaturiLorella Pasquinucci
Jul 25, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lorella PasquinucciRita Turnaturi
Apr 3, 2019·Journal of Medicinal Chemistry·Elisabeth KronenbergBernhard Wünsch

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