Structural and electronic requirements for potent agonists at a nicotinic receptor

Document Type

Article

Publication Date

1-14-1986

Abstract

A new agonist, isoarecolone methiodide (1,1-dimethyl-4-acetyl-1,2,3,6-tetrahydropyridinium iodide) was tested at the frog neuromuscular junction. It was 50 times more potent than carbamylcholine, making it one of the most potent nicotinic agonists known. In addition, its cyclic structure and conjugated carbonyl bond endow it with near rigidity. An analogous compound, 1,1-dimethyl-4-acetylpiperazinium iodide, was synthesized because of its similar geometry and rigidity. It was 2.6 times as potent as carbamylcholine but only 0.053 times as potent as isoarecolone methiodide. Computer assisted molecular modeling and molecular orbital calculations revealed steric and electrostatic field differences between these two compounds. © 1986.

Identifier

0022620350 (Scopus)

Publication Title

European Journal of Pharmacology

External Full Text Location

https://doi.org/10.1016/0014-2999(86)90652-7

ISSN

00142999

PubMed ID

3485051

First Page

127

Last Page

131

Issue

1

Volume

120

Grant

85-990670-5

Fund Ref

State of New Jersey Commission on Science and Technology

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