Salvatella Mariona, Arsequell Gemma, Valencia Gregorio, Rodríguez Raquel E
Unit of Glycoconjugate Chemistry, Instituto de Investigaciones Químicas y Ambientales, Jordi Girona 18-26, 08034-Barcelona, Spain.
Bioorg Med Chem Lett. 2004 Feb 23;14(4):905-8. doi: 10.1016/j.bmcl.2003.12.016.
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.