Quantification of [1-(5-fluoropentyl)-1H-indol-3-yl](naphthalene-1-yl)methanone (AM-2201) and 13 metabolites in human and rat plasma by liquid chromatography-tandem mass spectrometry

J Chromatogr A. 2016 Jun 17:1451:97-106. doi: 10.1016/j.chroma.2016.05.020. Epub 2016 May 6.

Abstract

AM-2201 is a popular synthetic cannabinoid first synthesized in 2000. AM-2201 pharmacokinetic and pharmacodynamic data are scarce, requiring further investigation. We developed a sensitive method for quantifying AM-2201 and 13 metabolites in plasma to provide a tool to further metabolic, pharmacokinetic and pharmacodynamic studies. Analysis was performed by liquid chromatography-tandem mass spectrometry. Chromatographic separation was performed by gradient elution on a biphenyl column with 0.1% formic acid in water/0.1% formic acid in acetonitrile:methanol 50:50 (v/v) mobile phase. Sample preparation (75μL) consisted of an enzymatic hydrolysis and a supported liquid extraction. The method was validated with human plasma with a 0.025 or 0.050-50μg/L working range, and cross-validated for rat plasma. Analytical recovery was 88.8-110.1% of target concentration, and intra- (n=30) and inter-day (n=30) imprecision<11.9% coefficient of variation. Method recoveries and matrix effects ranged from 58.4-84.4% and -62.1 to -15.6%, respectively. AM-2201 and metabolites were stable (±20%) at room temperature for 24h, at 4°C for 72h, and after three freeze-thaw cycles, and for 72h in the autosampler after extraction. The method was developed for pharmacodynamic and pharmacokinetic studies with controlled administration in rats but is applicable for pre-clinical and clinical research and forensic investigations. Rat plasma specimen analysis following subcutaneous AM-2201 administration demonstrated the suitability of the method. AM-2201, JWH-018 N-(5-hydroxypentyl), and JWH-018 N-pentanoic acid concentrations were 4.8±1.0, 0.15±0.03, and 0.34±0.07μg/L, respectively, 8h after AM-2201 administration at 0.3mg/kg (n=5).

Keywords: AM-2201; Liquid chromatography-tandem mass spectrometry; Metabolites; Plasma; Synthetic cannabinoid.

Publication types

  • Validation Study

MeSH terms

  • Animals
  • Cannabinoids / blood
  • Cannabinoids / metabolism
  • Cannabinoids / pharmacokinetics
  • Chromatography, Liquid / methods*
  • Humans
  • Indoles / administration & dosage
  • Indoles / blood*
  • Indoles / metabolism*
  • Indoles / pharmacokinetics
  • Naphthalenes / administration & dosage
  • Naphthalenes / blood*
  • Naphthalenes / metabolism*
  • Naphthalenes / pharmacokinetics
  • Pentanoic Acids / blood
  • Rats
  • Tandem Mass Spectrometry / methods*

Substances

  • 1-(5-fluoropentyl)-3-(1-naphthoyl)indole
  • Cannabinoids
  • Indoles
  • Naphthalenes
  • Pentanoic Acids
  • 1-pentyl-3-(1-naphthoyl)indole
  • n-pentanoic acid