A study of the metabolism of methamphetamine and 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in isolated rat hepatocytes

Forensic Sci Int. 2005 Mar 10;148(2-3):131-7. doi: 10.1016/j.forsciint.2004.04.084.

Abstract

The metabolism of methamphetamine (MA) and 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in freshly isolated rat hepatocytes was investigated, and compared with in vivo results. A suspended hepatocyte culture, established from male Wistar rats using a collagenase perfusion technique, was incubated in the presence of MA or 2C-B. After enzymatic hydrolysis of the conjugated forms, the metabolites were extracted by liquid-liquid partition and analyzed by gas chromatography/mass spectrometry (GC/MS). Amphetamine, p-hydroxymethamphetamine and p-hydroxyamphetamine were detected in the culture fluids of the rat hepatocytes inoculated with MA. The alcohol derivative, carboxylic acid derivative, 2-O-desmethyl-2C-B, 2-O-desmethyl-N-acetyl-2C-B and 5-O-desmethyl-N-acetyl-2C-B were detected in the case of 2C-B. The major metabolite of MA in rat hepatocytes was p-hydroxymethamphetamine. This is in good agreement with the urinary excretion profile for rats that were fed MA. 2-O-Desmethyl-2C-B and the carboxylic acid derivative were the major recovered metabolites of 2C-B in the rat hepatocyte culture, a slight deviation from the in vivo findings, in which 5-O-desmethyl-N-acetyl-2C-B was found to be the main component. Metabolites with a hydroxy group were largely present in their conjugated forms in the culture fluids, except for 2-O-desmethyl-2C-B. Taking these results into consideration, a primary hepatocyte culture system has the potential to provide a quick and handy method for estimating the in vivo metabolic fate of abused drugs.

MeSH terms

  • Amphetamine / metabolism
  • Animals
  • Carboxylic Acids / chemistry
  • Cells, Cultured
  • Central Nervous System Stimulants / metabolism*
  • DOM 2,5-Dimethoxy-4-Methylamphetamine / analogs & derivatives*
  • DOM 2,5-Dimethoxy-4-Methylamphetamine / metabolism*
  • Gas Chromatography-Mass Spectrometry
  • Hallucinogens / metabolism*
  • Hepatocytes / metabolism*
  • Male
  • Methamphetamine / analogs & derivatives*
  • Methamphetamine / metabolism*
  • Models, Animal
  • Molecular Structure
  • Rats
  • Rats, Wistar
  • Sympathomimetics / metabolism
  • p-Hydroxyamphetamine / metabolism

Substances

  • 2-O-desmethyl-4-bromo-2,5-dimethoxyphenethylamine
  • 2-O-desmethyl-N-acetyl-4-bromo-2,5-dimethoxyphenethylamine
  • Carboxylic Acids
  • Central Nervous System Stimulants
  • Hallucinogens
  • Sympathomimetics
  • DOM 2,5-Dimethoxy-4-Methylamphetamine
  • 2,5-dimethoxy-4-bromoamphetamine
  • Methamphetamine
  • pholedrine
  • Amphetamine
  • p-Hydroxyamphetamine