Abstract
(-)-Codeine 1 was converted into previously unknown 7β-methyl-7,8-dihydrocodeine/morphine derivatives such as 13 via classical diaxial opening of α-epoxide 3. Several analogs exhibited dual μ/δ-agonist activity.
Keywords:
6,7-α-Epoxide; Metopon; Mixed μ/δ agonist; Opioid.
Copyright © 2013 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Codeine / analogs & derivatives*
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Codeine / pharmacology*
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Epoxy Compounds / chemistry
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Epoxy Compounds / pharmacology
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Humans
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Mice
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Models, Molecular
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Morphinans / chemistry
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Morphinans / pharmacology
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Receptors, Opioid, delta / agonists*
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Receptors, Opioid, delta / metabolism
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Receptors, Opioid, mu / agonists*
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Receptors, Opioid, mu / metabolism
Substances
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Epoxy Compounds
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Morphinans
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Receptors, Opioid, delta
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Receptors, Opioid, mu
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metopon
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Codeine