MOLECULAR BINDING OF 2-PHENYLETHYLAMINE BY β-CYCLODEXTRIN

Abstract

The paper considers the results of an experimental study of the synthesis of 2-phenylethylamine, a biogenic amine, which is the initial link in natural neurotransmitters and is used in pharmacological practice as an antidepressant and a remedy for the treatment of neurological disorders. The target amine was synthesized by reduction of phenylacetonitrile with lithium borohydride and decarboxylation of the sodium salt of phenylalanine. The reduction reaction proceeds in aqueous ethanol at room temperature, which increases the yield of the product. At the same time, the resulting product quickly passes in air into an insoluble carbonate. Decarboxylation occurs when the sodium salt of phenylalanine is fused with an alkali, which leads to the partial formation of a condensation product, 3,6-dibenzylpiperazine-2,5-dione, at a high temperature. It is shown that both methods lead to the synthesis of the product with yields of about 45%. The inclusion complex of phenylethylamine with β-cyclodextrin, acting as an encapsulator - a container for molecular binding, was obtained by the suspension method. Binding occurs in an aqueous suspension, followed by washing the amine with acetone. The structure of the obtained compounds was proved by the method of nuclear magnetic resonance spectroscopy on 1H nuclei, as well as by thin-layer chromatography. Comparison of the integral intensities of the signals of the protons of the cyclodextrin framework and protons of the amino group of phenylethylamine showed that the process is accompanied by a transition to the bound form of 65% amine at a ratio of cyclodextrin : amine 3:2. It can be expected that such binding can be used in pharmacological practice to increase the stability of the amine, its targeted transport in the body and prevent premature processes of its destruction under the action of the monoamine oxygenase enzyme.