Date of Award

Spring 1985

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry & Biochemistry

Program/Concentration

Chemistry

Committee Director

Roy L. Williams

Committee Member

Robert L. Ake

Committee Member

Charles E. Bell

Committee Member

John D. Van Norman

Call Number for Print

Special Collections LD4331.C45J632

Abstract

Based on an interpretation of the literature of phencyclidine (PCP) together with an examination of the relevant models or prototype structures, this research has attempted to design and synthesize a rigid analog of the phencyclidine structure. The parent ring systems suggested for this study were the 1-arnino and 2-arninornethyltetralins, 10 and, 12.

Several organic compounds, based on this design, have been prepared by classical examples of reductive alkylation reactions of the corresponding 2-hydroxyciethylene-1-tetralones, 11, and by the condensation and subsequent reductive alkylation of the 1-arninotetralin, 9. These arninomethyltetralones, 28, 29 and 30, together with an example of a substituted 1-arninotetralin, 32, have been prepared and properly characterized using classical analytical and spectral techniques. These compounds are illustrated below.

The biological evaluation of these compounds remains incomplete due to the general insolubility of the respective hydrochlorides of arninomethyltetralone. Based on the preliminary data obtained from intraperitoneal injections of three of these compounds, 28, 29., and, 32, as well as intracerebroventricular injections, all in mice, it would appear that these compounds do not possess any PCP agonist or antagonist activity.

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DOI

10.25777/h625-5c38

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