Abstract
Four stereoisomers 1a-d of cis-fluoro-ohmefentanyl have been synthesized. Their absolute configurations were determined by X-ray analysis of (3S,4R,2'S)-(-)-cis-I d. The analgesic activity (mice, sc, hot plate) revealed extreme stereodifferences. The ED50 value of (3R,4S,2'S)-(+)-cis-I (1a) was 0.000774 mg/kg (17958 times more potent than that of morphine), while the corresponding antipode 1c was almost inactive.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Analgesics, Opioid / chemical synthesis*
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Analgesics, Opioid / pharmacology*
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Animals
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Chemical Phenomena
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Chemistry, Physical
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Crystallography, X-Ray
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Fentanyl / analogs & derivatives
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Fentanyl / chemical synthesis*
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Fentanyl / pharmacology
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Indicators and Reagents
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Magnetic Resonance Spectroscopy
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Mice
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Molecular Conformation
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Morphine / pharmacology
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Analgesics, Opioid
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Indicators and Reagents
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cis-fluoro-ohmefentanyl
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Morphine
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Fentanyl