Abstract
The aliphatic side chain plays a pivotal role in determining the cannabinergic potency of tricyclic classical cannabinoids. We have synthesized a series of analogues in which the C3 position is substituted either directly or through a one-carbon atom linker with an adamantylamine or with an oxa- or an oxazaadamantane. The oxaadamantane pharmacophore in analogue 16 showed the best binding profile for both receptors.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Adamantane / analogs & derivatives*
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Adamantane / chemical synthesis*
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Adamantane / pharmacology
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Animals
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Brain / metabolism
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Cannabinoids / chemical synthesis*
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Cannabinoids / pharmacology
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Cell Line
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Humans
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In Vitro Techniques
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Mice
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Models, Molecular
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Radioligand Assay
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Rats
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Receptor, Cannabinoid, CB1 / metabolism*
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Receptor, Cannabinoid, CB2 / metabolism*
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Structure-Activity Relationship
Substances
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Cannabinoids
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Receptor, Cannabinoid, CB1
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Receptor, Cannabinoid, CB2
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Adamantane