Title: An ab initio study on 3,4-methylenedioxymethamphetamine, MDMA (ecstasy) and its derivatives

Authors: Zahra Fallah Ebrahimi

Addresses: Department of Chemical Engineering, École Polytechnique de Montréal, Montréal, QC H3T 1J4, Canada

Abstract: Computational studies have been carried out at DFT-B3LYP/6-31+G* and PW91P86/6-31+G* levels of theory on the structural and spectroscopic properties of 3,4-methylenedioxymethamphetamine (MDMA) and its derivatives. Nuclear quadrupole coupling constants (NQCCs) of 14N and 17O and chemical shift of 13C and 1H have been calculated. There is a good correlation between the calculated chemical shifts of 13C and 1H and experimental data. Our results showed that 14N and 17O NQCCs are quite sensitive to substitute-induced structural charge. In these compounds, a correlation has been observed between the parameters characteristic biological activity (LD50, IC50) and nuclear quadruple resonance (NQR) parameters. We also report a computational study for the 14N and 17O nuclear magnetic resonance (NMR) tensors in ecstasy and its derivatives. To our knowledge, no sufficient ab initio study has been carried out on MDMA and its derivatives.

Keywords: ab initio study; 3,4-methylenedioxymethamphetamine; MDMA; NQCCs; nuclear quadrupole coupling constants; ecstasy; nuclear magnetic resonance; NMR tensors; NQR; LD50; IC50; structural properties; spectroscopic properties; computational studies; recreational drugs.

DOI: 10.1504/IJCBDD.2016.074986

International Journal of Computational Biology and Drug Design, 2016 Vol.9 No.1/2, pp.149 - 161

Available online: 26 Feb 2016 *

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