A highly toxic morphine-3-glucuronide derivative

M Salvatella, G Arsequell, G Valencia…

Index: Salvatella, Mariona; Arsequell, Gemma; Valencia, Gregorio; Rodriguez, Raquel E. Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 4 p. 905 - 908

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Citation Number: 3

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 (ip) 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.