Abstract
A series of C1, C2, C3 and N6 analogs of nantenine (2) was synthesized and evaluated in 5-HT(2A) and α(1A) receptor functional assays. Alkyl substitution of the C1 and N6 methyl groups of nantenine provided selective 5-HT(2A) and α(1A) antagonists, respectively. The C2 alkyloxy analogs studied were generally selective for α(1A) versus 5-HT(2A). The C3 bromo analog 15 is one of the most potent aporphinoid 5-HT(2A) antagonists known presently.
Copyright © 2011 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Adrenergic alpha-1 Receptor Antagonists / chemical synthesis
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Adrenergic alpha-1 Receptor Antagonists / chemistry*
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Adrenergic alpha-1 Receptor Antagonists / pharmacology
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Aporphines / chemical synthesis
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Aporphines / chemistry*
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Aporphines / pharmacology
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Receptor, Serotonin, 5-HT2A / chemistry*
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Receptor, Serotonin, 5-HT2A / metabolism
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Receptors, Adrenergic, alpha-1 / chemistry*
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Receptors, Adrenergic, alpha-1 / metabolism
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Serotonin 5-HT2 Receptor Antagonists / chemical synthesis
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Serotonin 5-HT2 Receptor Antagonists / chemistry*
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Serotonin 5-HT2 Receptor Antagonists / pharmacology
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Structure-Activity Relationship
Substances
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3-bromonantenine
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Adrenergic alpha-1 Receptor Antagonists
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Aporphines
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Receptor, Serotonin, 5-HT2A
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Receptors, Adrenergic, alpha-1
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Serotonin 5-HT2 Receptor Antagonists
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nantenine