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. 2018 Apr 26;9:414. doi: 10.3389/fphar.2018.00414

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Copyright © 2018 Kirla, Groh, Poetzsch, Banote, Stadnicka-Michalak, Eggen, Schirmer and Kraemer.

This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

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Schematic representation of possible binding sites of melanin with mCPP and cocaine. Box 1 and box 2 are selected sites of melanin proposed to be important for the interactions with chemicals. (a1) an example of an ionic interaction between a carboxylic acid and a protonated nitrogen (solid line) between melanin and cocaine/mCPP; (a2) additional ionic interaction site in cocaine with a carboxylic acid group; (b1) interactions between aromatic rings of melanin and cocaine/mCPP (solid line); (b2) an example of a double bond site in cocaine for the interaction with aromatic rings of melanin; (c) an example of a charge-transfer reaction site (oxygen) possible only in cocaine; (d) an example of hydrogen bridging site with five hydrogen acceptor sites in cocaine and only two in mCPP (indicated by asterisk). For example, Eumelanin structure has been adapted and modified from Karlsson and Lindquist (2016).