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

Received: 26 Jun 2015
Accepted: 21 Jul 2015
Published online: 28 Feb 2016 *

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