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Insights into Interactions of N-Ethylpentylone Drug with Water and Biomacromolecules

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Abstract

One of the new synthetic cathinones that has a high tendency to replace ecstasy and other established synthetic drugs is N-ethylpentylone, (NEP), due to its high potency, stimulative, hedonic and hallucinatory effects. In order to examine the interactions of N-ethylpentylone, the apparent molar quantities, thermal expansion coefficient and the apparent molar volume at infinite dilution were calculated from the experimental measurements of the density of NEP aqueous solutions in different temperature and molality ranges, from T = (293.15 to 313.15) K and from m = (0.0590 to 0.0977) mol·kg−1, respectively. The taste of N-ethylpentylone was estimated by calculated values of apparent specific molar volume at infinite dilution and it was concluded that its taste in aqueous solutions is bitter. Also, using the spectrofluorimetric technique, an intermolecular deactivation of in situ formed ethidium bromide (EB) complex with DNA (EB-DNA) was investigated in the presence of N-ethylpentylone. Obtained results indicated good affinity and efficiency of NEP to substitute EB from the EB-DNA complex via intercalation mode. Using molecular docking, it was concluded that the binding energy obtained for NEP indicates its higher affinity to interact with DNA, compared to methamphetamine and amphetamine, but lower compared to ecstasy. The affinity of NEP to bind to bovine serum albumin (BSA) was also investigated and discussed. It is shown that N-ethylpentylone could be efficiently transported and distributed through the blood and cells.

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Funding

This work is performed under financial support of the Ministry of Education, Science and Technological Development of the Republic of Serbia (Grant No. 451-03-68‬/2020-14‬/200125). The authors hereby declare no existing financial interests concerning these research studies.

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Authors and Affiliations

  1. Faculty of Science, University of Novi Sad, Trg D. Obradovića 3, Novi Sad, 21000, Serbia

    Sanja Belić, Marija Petrin Miličević, Milan Vraneš, Aleksandar Tot, Jovana Nikolov, Nikolett Cakó Bagány & Slobodan Gadžurić

  2. Department of Science, Institute for Information Technologies, University of Kragujevac, Jovana Cvijića bb, Kragujevac, 34000, Serbia

    Nenad Janković

  3. Department for Physical-Chemical and Toxicological Expertises, Ministry of Interior of Republic of Serbia, National Forensic Center, Belgrade, 11000, Serbia

    Nataša Radosavljević Stevanović

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  1. Sanja Belić
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Contributions

SB, MPM and NCB conducted measurements, sample preparation, calculation of volumetric properties and wrote the first draft of the manuscript; NJ measured interactions with biomacromolecules; AT performed molecular docking; NRS supplied chemicals and seizure illicit drug samples; JN, MV and SG interpreted results and reviewed manuscript.

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Correspondence to Slobodan Gadžurić.

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Belić, S., Miličević, M.P., Vraneš, M. et al. Insights into Interactions of N-Ethylpentylone Drug with Water and Biomacromolecules. J Solution Chem (2024). https://doi.org/10.1007/s10953-024-01369-5

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