title: A highly toxic morphine-3-glucuronide derivative.
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.
authors.affiliation: Unit of Glycoconjugate Chemistry, Instituto de Investigaciones Químicas y Ambientales, Jordi Girona 18-26, 08034-Barcelona, Spain.
authors.forename: Mariona
authors.initials: M
authors.lastname: Salvatella
authors.forename: Gemma
authors.initials: G
authors.lastname: Arsequell
authors.forename: Gregorio
authors.initials: G
authors.lastname: Valencia
authors.forename: Raquel E
authors.initials: RE
authors.lastname: Rodríguez
mesh_terms: D000818:Animals; D001522:Behavior, Animal / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D051379:Mice; D015394:Molecular Structure; D009020:Morphine / Q000008:administration & dosage / Q000037:antagonists & inhibitors / Q000494:pharmacology; D009022:Morphine Derivatives / Q000138:chemical synthesis / Q000494:pharmacology / Q000633:toxicity*; D009270:Naloxone / Q000494:pharmacology; D009292:Narcotic Antagonists; D051381:Rats; D011957:Receptors, Opioid / Q000187:drug effects
chemical_list: D009022:Morphine Derivatives; D009292:Narcotic Antagonists; D011957:Receptors, Opioid; C490850:morphine-3-octylglucuronamide; D009270:Naloxone; D009020:Morphine; C018108:morphine-3-glucuronide