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Molecular Pharmacology

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Research ArticleArticle

Tautomerism and the Receptor Action of Histamine: a Mechanistic Model

HAREL WEINSTEIN, DAVID CHOU, CARL L. JOHNSON, SUNGZONG KANG and JACK PETER GREEN
Molecular Pharmacology September 1976, 12 (5) 738-745;
HAREL WEINSTEIN
Department of Pharmacology, Mount Sinai School of Medicine of the City University of New York, New York 10029
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DAVID CHOU
Department of Pharmacology, Mount Sinai School of Medicine of the City University of New York, New York 10029
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CARL L. JOHNSON
Department of Pharmacology, Mount Sinai School of Medicine of the City University of New York, New York 10029
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SUNGZONG KANG
Department of Pharmacology, Mount Sinai School of Medicine of the City University of New York, New York 10029
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JACK PETER GREEN
Department of Pharmacology, Mount Sinai School of Medicine of the City University of New York, New York 10029
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Abstract

The effect of deprotonation of histamine monocation on the dominant tautomeric forms of the molecule was analyzed theoretically from molecular orbital calculations ab initio. The electron charge redistribution caused by the interaction of the monocation with a negatively charged group. In both cases the result is a shift in the dominant tautomeric form caused by a change in the reactivity of the ring nitrogens, as demonstrated by the molecular electrostatic potentials and total molecular energies. A model for the role of this induced tautomerism in the activation of the histamine H2 receptor is proposed on the basis of these findings.

ACKNOWLEDGMENTS The computations were supported in part by a grant of computer time from the Central Computer Facility of the City University of New York. The authors are grateful to Dr. W. F. Raub and the Chemical/Biological Information-Handling Program, Division of Research, National Institutes of Health, for providing access to the PROPHET system computer.

  • Copyright © 1976 by Academic Press, Inc.

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Molecular Pharmacology
Vol. 12, Issue 5
1 Sep 1976
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Research ArticleArticle

Tautomerism and the Receptor Action of Histamine: a Mechanistic Model

HAREL WEINSTEIN, DAVID CHOU, CARL L. JOHNSON, SUNGZONG KANG and JACK PETER GREEN
Molecular Pharmacology September 1, 1976, 12 (5) 738-745;

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Research ArticleArticle

Tautomerism and the Receptor Action of Histamine: a Mechanistic Model

HAREL WEINSTEIN, DAVID CHOU, CARL L. JOHNSON, SUNGZONG KANG and JACK PETER GREEN
Molecular Pharmacology September 1, 1976, 12 (5) 738-745;
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