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A highly toxic morphine-3-glucuronide derivative

AuthorsSalvatella, Mariona; Arsequell, Gemma ; Valencia Parera, Gregorio; Rodríguez, Raquel E.
KeywordsMorphine glucuronides
Opioid antagonists
Alkyl glycosides
Issue Date4-Jan-2004
CitationBioorganic and Medicinal Chemistry Letters 14(4): 905-908 (2004)
AbstractBy 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.
A morphine-3-glucuronide conjugate to octylamine is a lethal compound even at ng/kg doses. However, its closely related amide analogue lacking the octyl chain acts as opioid antagonist in a similar pattern than naloxone.
Description4 pages, 1 figure, 4 tables.-- 15012991 [PubMed].-- Printed version published Feb 23, 2004.
Publisher version (URL)http://dx.doi.org/10.1016/j.bmcl.2003.12.016
Appears in Collections:(IQAC) Artículos
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