PMID- 12731652
OWN - NLM
STAT- MEDLINE
DCOM- 20040202
LR  - 20190513
IS  - 0146-4760 (Print)
IS  - 0146-4760 (Linking)
VI  - 27
IP  - 3
DP  - 2003 Apr
TI  - Cocaine, benzoylecgonine, amphetamine, and N-acetylamphetamine binding to melanin 
      subtypes.
PG  - 125-34
AB  - 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.
FAU - Borges, Chad R
AU  - Borges CR
AD  - Department of Pharmacology and Toxicology, University of Utah, Salt Lake City, 
      Utah, USA. borges@pilot.msu.edu
FAU - Roberts, Jeanette C
AU  - Roberts JC
FAU - Wilkins, Diana G
AU  - Wilkins DG
FAU - Rollins, Douglas E
AU  - Rollins DE
LA  - eng
GR  - DA07820/DA/NIDA NIH HHS/United States
PT  - Comparative Study
PT  - Journal Article
PT  - Research Support, U.S. Gov't, P.H.S.
PL  - England
TA  - J Anal Toxicol
JT  - Journal of analytical toxicology
JID - 7705085
RN  - 0 (Amphetamines)
RN  - 0 (Central Nervous System Stimulants)
RN  - 0 (Indoles)
RN  - 0 (Melanins)
RN  - 0 (pheomelanin)
RN  - 12627-86-0 (eumelanin)
RN  - 14383-60-9 (N-acetylamphetamine)
RN  - 4790-08-3 (5,6-dihydroxy-2-indolylcarboxylic acid)
RN  - 5353I8I6YS (benzoylecgonine)
RN  - CK833KGX7E (Amphetamine)
RN  - I5Y540LHVR (Cocaine)
RN  - Z3OC8499KG (5,6-dihydroxyindole)
SB  - IM
MH  - Amphetamine/chemistry
MH  - Amphetamines/chemistry
MH  - Central Nervous System Stimulants/*chemistry
MH  - Chromatography, Liquid
MH  - Cocaine/*analogs & derivatives/chemistry
MH  - Hair/chemistry
MH  - Hair Color
MH  - Indoles/chemistry
MH  - Mass Spectrometry
MH  - Melanins/*chemistry
EDAT- 2003/05/07 05:00
MHDA- 2004/02/03 05:00
CRDT- 2003/05/07 05:00
PHST- 2003/05/07 05:00 [pubmed]
PHST- 2004/02/03 05:00 [medline]
PHST- 2003/05/07 05:00 [entrez]
AID - 10.1093/jat/27.3.125 [doi]
PST - ppublish
SO  - J Anal Toxicol. 2003 Apr;27(3):125-34. doi: 10.1093/jat/27.3.125.