Abstract
The syntheses of trans- and cis-1-benzyl-3-dimethylamino-6-phenylpiperidine (1 and 2) are described. Compounds 1 and 2 were found to be inhibitors to histamine, acetylcholine, and barium chloride induced contractions of the isolated guinea pig ileum. Compounds 1 and 2 do not exhibit appreciable stereoselectivity in their ability to inhibit smooth muscle contractions. The cis compound 2 is a more effective inhibitor of histamine N-methyltransferase than the trans isomer 1.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Acetylcholine / pharmacology
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Animals
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Barium / pharmacology
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Dimethylamines / chemical synthesis
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Dimethylamines / pharmacology
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Guinea Pigs
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Histamine / pharmacology
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Histamine H1 Antagonists / chemical synthesis*
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Histamine N-Methyltransferase / antagonists & inhibitors
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Ileum / drug effects
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In Vitro Techniques
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Molecular Conformation
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Muscle Contraction / drug effects
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Muscle, Smooth / drug effects
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Piperidines / chemical synthesis*
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Piperidines / pharmacology
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Receptors, Drug*
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Dimethylamines
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Histamine H1 Antagonists
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Piperidines
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Receptors, Drug
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Barium
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Histamine
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Histamine N-Methyltransferase
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Acetylcholine