Abstract
A series of aryl tropanyl esters and amides related to 1H-indole-3-carboxylic acid endo 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester (ICS 205930, CAS 89565-68-4) were synthesized and evaluated for antinociceptive activity using the hot-plate test. Of these, the benzofurane-3-carboxylic ester of tropine (1) was found powerfully to increase the pain threshold, with a cholinergic mechanism of action. Despite the structural similarity with ICS 205930, the analgesia induced by 1 seems not to be due to 5-HT3 receptor interaction, and there is evidence of involvement of the central 5-HT4 receptor.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Analgesics / chemical synthesis*
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Analgesics / pharmacology
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Animals
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Cerebral Cortex / drug effects
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Cerebral Cortex / metabolism
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In Vitro Techniques
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Indoles / chemical synthesis*
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Indoles / pharmacology
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Male
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Membranes / metabolism
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Mice
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Naloxone / pharmacology
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Pain Measurement / drug effects
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Rats
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Rats, Wistar
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Receptors, Muscarinic / drug effects
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Receptors, Serotonin / drug effects
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Serotonin Antagonists / pharmacology
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Serotonin Receptor Agonists / chemical synthesis*
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Serotonin Receptor Agonists / pharmacology
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Structure-Activity Relationship
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Tropanes / chemical synthesis*
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Tropanes / pharmacology
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Tropisetron
Substances
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Analgesics
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Indoles
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Receptors, Muscarinic
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Receptors, Serotonin
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Serotonin Antagonists
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Serotonin Receptor Agonists
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Tropanes
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Naloxone
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Tropisetron