A highly toxic morphine-3-glucuronide derivative.
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.
Salvatella
Mariona
M
Unit of Glycoconjugate Chemistry, Instituto de Investigaciones Químicas y Ambientales, Jordi Girona 18-26, 08034-Barcelona, Spain.
Arsequell
Gemma
G
Valencia
Gregorio
G
Rodríguez
Raquel E
RE
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
D009022:Morphine Derivatives; D009292:Narcotic Antagonists; D011957:Receptors, Opioid; C490850:morphine-3-octylglucuronamide; D009270:Naloxone; D009020:Morphine; C018108:morphine-3-glucuronide