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| Title: | A highly toxic morphine-3-glucuronide derivative |
Authors: | Salvatella, Mariona; Arsequell, Gemma CSIC ORCID; Valencia Parera, Gregorio; Rodríguez, Raquel E. | Keywords: | Morphine glucuronides M3G Opioid antagonists Alkyl glycosides |
Issue Date: | 4-Jan-2004 | Publisher: | Elsevier | Citation: | Bioorganic and Medicinal Chemistry Letters 14(4): 905-908 (2004) | 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. 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. |
Description: | 4 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 | URI: | http://hdl.handle.net/10261/19038 | DOI: | 10.1016/j.bmcl.2003.12.016 | ISSN: | 0960-894X | E-ISSN: | 1464-3405 |
| Appears in Collections: | (IQAC) Artículos |
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