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Macrocyclic polyamines as a possible chemical model for histamine H2-receptors

DOI: 10.1248/cpb.32.3569

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 3569 - 5578 (1984)

Update date:2022-08-11

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Authors:

KimuraKimura

KoikeKoike

KodamaKodama

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Article abstract of DOI:10.1248/cpb.32.3569

An 18-membered macrocyclic hexaamine, [18]aneN6, interacts with histamine and its H2-agonist dimaprit at physiological pH to yield stable 1:1 complexes with simultaneous liberation of H+ which mimics the histamine H2-receptor-agonist interaction and the resulting gastric acid secretion. The polyamine H2-receptor model does not interact with the histamine H1-agonist 2-pyridylethylamine. Our model does interact with the H2-antagonists cimetidine, metiamide, famotidine and ranitidine to form more stable 1:1 complexes than with the H2-agonists, which offers a possible chemical model for the pharmacological ability of the H2-antagonists to competitively block H2-receptors and inhibit the gastric acid secretion induced by histamine. The known structural features distinguishing between histamine H1- and H2-agonist, and between histamine H2-agonist and -antagonist are reevaluated in terms of our model.

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Full text of DOI:10.1248/cpb.32.3569

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