A highly toxic morphine-3-glucuronide derivative

Bioorg Med Chem Lett. 2004 Feb 23;14(4):905-8. doi: 10.1016/j.bmcl.2003.12.016.

Abstract

By the coupling of octylamine to the uronic acid function of morphine-3-glucuronide (M3G) a new glycoconjugate (morphine-3-octylglucuronamide, M3GOAM) was prepared. When assayed in both rats and mice up to ng/kg (i.p.) doses none of the animals survived. The aliphatic octyl chain may be the lethal factor since a closely related derivative (M3GNH2), was not toxic and showed similar opioid antagonist properties than naloxone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Behavior, Animal / drug effects
  • Dose-Response Relationship, Drug
  • Mice
  • Molecular Structure
  • Morphine / administration & dosage
  • Morphine / antagonists & inhibitors
  • Morphine / pharmacology
  • Morphine Derivatives / chemical synthesis
  • Morphine Derivatives / pharmacology
  • Morphine Derivatives / toxicity*
  • Naloxone / pharmacology
  • Narcotic Antagonists
  • Rats
  • Receptors, Opioid / drug effects

Substances

  • Morphine Derivatives
  • Narcotic Antagonists
  • Receptors, Opioid
  • morphine-3-octylglucuronamide
  • Naloxone
  • Morphine
  • morphine-3-glucuronide