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Intermolecular interactions between DNA and methamphetamine, amphetamine, ecstasy and their major metabolites.

Arthur F V F Reis, Igor L P Gonçalves, Abel F G Neto, Alberdan S Santos, Kamil Kuča, Eugenie Nepovimová, Antonio M J C Neto

Journal of biomolecular structure & dynamics September 2018 DOI: 10.1080/07391102.2017.1386592 (opens in new tab)

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AI-extracted from the abstract
Characteristics Theoretical or computational study (molecular docking and molecular dynamics simulations) Peer reviewed
Population Human DNA fragments (computational receptor models), interacting with amphetamine-type stimulants and their metabolites
Interventions Amphetamine Methamphetamine 3
Measures Free Gibbs change of binding (ΔGbind)
Topics MDMA
Keywords Dna Methamphetamine Molecular simulations
Key points The authors report that MDMA and its metabolite DHMA bind preferentially to the minor groove of human DNA, with DHMA showing more spontaneous binding (ΔGbind = -13.15 kcal/mol) than MDMA (ΔGbind = -8.61 kcal/mol). They suggest these molecules have a greater probability of causing damage to human DNA fragments, based on simulation calculations rather than experimental evidence.

Abstract

In this work, we carried out a theoretical investigation regarding amphetamine-type stimulants, which can cause central nervous system degeneration, interacting with human DNA. These include amphetamine, methamphetamine, 3,4-Methylenedioxymethamphetamine (also known as ecstasy), as well as their main metabolites. The studies were performed through molecular docking and molecular dynamics simulations, where molecular interactions of the receptor-ligand systems, along with their physical-chemical energies, were reported. Our results show that 3,4-Methylenedioxymethamphetamine and 3,4-Dihydroxymethamphetamine (ecstasy) present considerable reactivity with the receptor (DNA), suggesting that these molecules may cause damage due to human-DNA. These results were indicated by free Gibbs change of bind (ΔGbind) values referring to intermolecular interactions between the drugs and the minor grooves of DNA, which were predominant for all simulations. In addition, it was observed that 3,4-Dihydroxymethamphetamine (ΔGbind = -13.15 kcal/mol) presented greater spontaneity in establishing interactions with DNA in comparison to 3,4-Methylenedioxymethamphetamine (ΔGbind = -8.61 kcal/mol). Thus, according with the calculations performed our results suggest that the 3,4-Methylenedioxymethamphetamine and 3,4-Dihydroxymethamphetamine have greater probability to provide damage to human DNA fragments.

Comparable studies

Other theoretical and historical papers on MDMA, most cited first.

Study Year Design Participants
Differences Between the Mechanism of Action of MDMA, MBDB, and the Classic Hallucinogens. Identification of a New Therapeutic Class: Entactogens 1986 Theoretical or philosophical paper
The Background and Chemistry of MDMA 1986 Historical analysis
The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents* Original documents in Merck's historical archive in Darmstadt, Germany, years 1900–1960 2006 Historical analysis
Distinct neural mechanisms for the prosocial and rewarding properties of MDMA 2019 Theoretical or philosophical paper
How could MDMA (ecstasy) help anxiety disorders? A neurobiological rationale 2009 Theoretical or philosophical paper

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