(+/-)-trans-2-(Aminomethyl)cyclobutanecarboxylic acid hydrochloride: a rigid analogue of gamma-aminobutyric acid

J Med Chem. 1980 Oct;23(10):1142-4. doi: 10.1021/jm00184a017.

Abstract

The (+/-) title compound was prepared to evaluate prior observations that certain gamma-aminobutyric acid (gamma Abu) congeners in the transoid disposition demonstrate gamma Abu receptor binding activity. It was prepared by a multistep sequence from (+/-)-methyl trans-2-(hydroxymethyl)cyclobutanecarboxylate. In a sodium-independent binding assay, the specific binding of (+/-)-1 to synaptic membranes from rat brain tissue was 1/14 500 that of gamma Abu.

MeSH terms

  • Animals
  • Binding Sites
  • Binding, Competitive
  • Cyclobutanes / chemical synthesis*
  • Cyclobutanes / metabolism
  • In Vitro Techniques
  • Rats
  • Synaptic Membranes / metabolism
  • gamma-Aminobutyric Acid / metabolism*

Substances

  • Cyclobutanes
  • gamma-Aminobutyric Acid
  • 2-(aminomethyl)cyclobutanecarboxylic acid