Cocaine, benzoylecgonine, amphetamine, and N-acetylamphetamine binding to melanin subtypes

Chad Borges, Jeanette C. Roberts, Diana G. Wilkins, Douglas E. Rollins

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

Experiments have been performed to document the in vitro binding of cocaine, benzoylecgonine (BE), amphetamine, and N-acetylamphetamine (N-AcAp) to synthetic melanin subtypes. The two predominant melanin types in hair are the black eumelanins and the reddish-brown pheomelanins. The melanins included in this study are two black eumelanin subtypes [5,6-dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA) derived melanins], a reddish-brown pheomelanin [from 5-cysteinyl-S-Dopa (5-CysDOPA)], and two mixed eu/pheomelanin copolymers. Results indicate that the basic drugs cocaine and amphetamine bind to eumelanins and mixed eu/pheomelanins to varying degrees, but not to pure pheomelanin. BE and N-AcAp, net neutral molecules, do not bind to any type of melanin. As a model of which eumelanin chemical functional groups bind drugs, amphetamine was shown, using tandem mass spectrometry, to form a noncovalent adduct with dimerized oxidized catechol. Similar functional groups on the eumelanin polymer may represent an important drug-binding site. Overall, these findings show that basic drugs have a greater affinity for melanin than their net neutral analogues, reveal that melanin types differ when it comes to drug binding, help elucidate what properties of melanin are important for drug binding, and help explain why hair color biases exist.

Original languageEnglish (US)
Pages (from-to)125-134
Number of pages10
JournalJournal of Analytical Toxicology
Volume27
Issue number3
StatePublished - Apr 2003
Externally publishedYes

Fingerprint

Melanin
melanin
Melanins
Amphetamine
Cocaine
drug
Pharmaceutical Preparations
hair
Functional groups
functional group
Hair Color
Dihydroxyphenylalanine
benzoylecgonine
N-acetylamphetamine
Binding sites
carboxylic acid
Tandem Mass Spectrometry
Carboxylic acids
Mass spectrometry
Polymers

ASJC Scopus subject areas

  • Analytical Chemistry
  • Toxicology
  • Health, Toxicology and Mutagenesis

Cite this

Cocaine, benzoylecgonine, amphetamine, and N-acetylamphetamine binding to melanin subtypes. / Borges, Chad; Roberts, Jeanette C.; Wilkins, Diana G.; Rollins, Douglas E.

In: Journal of Analytical Toxicology, Vol. 27, No. 3, 04.2003, p. 125-134.

Research output: Contribution to journalArticle

Borges, Chad ; Roberts, Jeanette C. ; Wilkins, Diana G. ; Rollins, Douglas E. / Cocaine, benzoylecgonine, amphetamine, and N-acetylamphetamine binding to melanin subtypes. In: Journal of Analytical Toxicology. 2003 ; Vol. 27, No. 3. pp. 125-134.
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