Pathways for Activating Isotope Exchange of Dopamine with D2O

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Abstract

Various methods of introducing deuterium into dopamine using isotope exchange are considered. The best result is achieved by isotope exchange with deuterated water at 190°C for 30 min using (a) trifluoroacetic acid as a catalyst and (b) 5% Pd/Al2O3 catalyst presaturated with deuterium gas. In the first case, the yield of deuterated dopamine was 65–70%, and the average deuterium content was 2.4–2.5 at./molecule. In the second case, the yield decreased to 35–40%, but the deuterium content increased to 3.50–3.60 at./molecule. The obtained result highlights the effectiveness of an integrated approach to introducing hydrogen isotopes into organic molecules, when activated hydrogen isotope species are formed on the catalyst and the substance deposited on it, which contribute to increasing the efficiency of isotope exchange with deuterated water when heated.

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About the authors

V. P. Shevchenko

National Research Centre Kurchatov Institute

Email: nagaev.img@yandex.ru
Russian Federation, pl. Kurchatova 2, Moscow, 123182

I. Y. Nagaev

National Research Centre Kurchatov Institute

Author for correspondence.
Email: nagaev.img@yandex.ru
Russian Federation, pl. Kurchatova 2, Moscow, 123182

N. F. Myasoedov

National Research Centre Kurchatov Institute

Email: nagaev.img@yandex.ru
Russian Federation, pl. Kurchatova 2, Moscow, 123182

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2. Fig. 1. Analysis of the reaction mixture on a Milichrome A-02 chromatograph after conducting preparative experiments (the first peak is dopamine): a – activation of isotopic exchange of TFA; b – activation of isotopic exchange of 5% Pd/Al2O3.

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3. 2. Isotopomers in [D]dopamine after conducting preparative experiments: a – activation of isotopic exchange of TFA; b – activation of isotopic exchange of 5% Pd/Al2O3.

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