Abstract
The N-demethylation of 3-deoxymorphine (1) was investigated using methyl chloroformate and hydrazine. 3-Deoxynormorphine (2) was obtained in 70% yield, and 3-deoxydihydronormorphine (3) was also obtained as a side product. The mu, delta, and kappa receptor binding affinity of a series of N-substituted 3-deoxynormorphines 6 and 7 and N-substituted 3-deoxydihydronormorphines 8-11 was also determined.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Animals
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CHO Cells
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Cell Membrane / chemistry
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Cricetinae
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Cricetulus
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Formates / chemistry
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Methylation
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Morphine / chemistry*
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Morphine / metabolism
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Morphine / pharmacology
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Morphine Derivatives*
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Narcotics / chemistry*
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Narcotics / pharmacology
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Receptors, Opioid / metabolism*
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Receptors, Opioid, delta / metabolism
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Receptors, Opioid, kappa / metabolism
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Receptors, Opioid, mu / metabolism
Substances
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3-deoxymorphine
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Formates
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Morphine Derivatives
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Narcotics
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Receptors, Opioid
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Receptors, Opioid, delta
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Receptors, Opioid, kappa
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Receptors, Opioid, mu
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Morphine
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methyl chloroformate