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Research ArticleArticle

AUTONOMIC BLOCKING COMPOUNDS. III. THE GANGLION BLOCKING AND PARASYMPATHOLYTIC ACTIONS OF A SERIES OF QUATERNARY AMMONIUM DERIVATIVES CONTAINING THE PHENOTHIAZINE NUCLEUS

Martin M. Winbury, Donald L. Cook and W. E. Hambourger
Journal of Pharmacology and Experimental Therapeutics August 1954, 111 (4) 395-403;
Martin M. Winbury
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Donald L. Cook
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W. E. Hambourger
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Abstract

The ganglion blocking and parasympatholytic actions of a series of quaternary ammonium derivatives of phenothiazine (PTZ) was studied. Almost all of the compounds produced ganglionic blockade; the most potent compound, 10-[2-(2,5-dimethyl-1-pyrollidinyl)ethyl] phenothiazine methobromide was three and one-half times as active as tetraethylammonium on a molar basis.

Compounds with greatest parasympatholytic activity have a two carbon alkylene chain linking the quaternary nitrogen to the PTZ nucleus. Introduction of a methyl side chain on the alkylene carbon adjacent (alpha) to the quaternary nitrogen improved both types of blocking action. However, introduction of a methylene, ethylene, carbonyl, carbonyloxy or amido group between the alkamine and the 10 position of the PTZ nucleus markedly decreased the parasympatholytic potency.

The nature of the N-alkyl groups had a significant influence on the parasympatholytic activity. Ethyl was superior to methyl but hydroxyethyl was inferior. The compound having the greatest activity was 10-[2-(1-diethylaminopropyl)] phenothiazine methochloride.

Footnotes

    • Received March 6, 1954.

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Journal of Pharmacology and Experimental Therapeutics
Vol. 111, Issue 4
1 Aug 1954
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AUTONOMIC BLOCKING COMPOUNDS. III. THE GANGLION BLOCKING AND PARASYMPATHOLYTIC ACTIONS OF A SERIES OF QUATERNARY AMMONIUM DERIVATIVES CONTAINING THE PHENOTHIAZINE NUCLEUS
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Research ArticleArticle

AUTONOMIC BLOCKING COMPOUNDS. III. THE GANGLION BLOCKING AND PARASYMPATHOLYTIC ACTIONS OF A SERIES OF QUATERNARY AMMONIUM DERIVATIVES CONTAINING THE PHENOTHIAZINE NUCLEUS

Martin M. Winbury, Donald L. Cook and W. E. Hambourger
Journal of Pharmacology and Experimental Therapeutics August 1, 1954, 111 (4) 395-403;

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Research ArticleArticle

AUTONOMIC BLOCKING COMPOUNDS. III. THE GANGLION BLOCKING AND PARASYMPATHOLYTIC ACTIONS OF A SERIES OF QUATERNARY AMMONIUM DERIVATIVES CONTAINING THE PHENOTHIAZINE NUCLEUS

Martin M. Winbury, Donald L. Cook and W. E. Hambourger
Journal of Pharmacology and Experimental Therapeutics August 1, 1954, 111 (4) 395-403;
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