Analyses of anandamide and endocannabinoid-like compounds using collision-induced dissociation in fast atom bombardment ionization-mass spectrometry and gas chromatography/chemical ionization-mass spectrometry

Anal Sci. 2003 Dec;19(12):1593-8. doi: 10.2116/analsci.19.1593.

Abstract

The utility of the collision-induced dissociation (CID) of two different forms of precursor cations generated by the fast atom bombardment (FAB) ionization of N-arachidonylethanolamine (anandamide) and a series of endocannabinoid-like compounds, such as N-oleoylethanolamine, N-palmitoylethanolamine, N-stearoylethanolamine, N-linoleoylethanolamine, N-oleoylpropanolamine, and N-palmitoylpropanolamine, as a method of providing general information on their characterizations was examined. The CID spectra of lithium-adduct [M+Li]+ ions of the amines with unsaturated hydrocarbon chains were rich in structurally informative charge-site-remote (CSR) fragmentation patterns that provide information on the locations of double bonds in hydrocarbon chains. On the other hand, the CID reactions of [M+H]+ ions produced acylium ions that are derived from the cleavage of amide bonds, thus providing information on the size of the hydrocarbon chains, although CSR fragmentations were not observed. These compounds without derivatization were analyzed using gas chromatography/chemical ionization-mass spectrometry (GC/CI-MS) with a polyethylene glycol phased column with fused silica capillary pre-tubing. Identifiable molecular-related [M+H]+ ions were observed.

MeSH terms

  • Arachidonic Acids / analysis*
  • Cannabinoid Receptor Modulators / analysis*
  • Endocannabinoids*
  • Ethanolamines / analysis
  • Fatty Acids, Unsaturated / analysis
  • Gas Chromatography-Mass Spectrometry / instrumentation
  • Gas Chromatography-Mass Spectrometry / methods*
  • Lithium
  • Polyunsaturated Alkamides
  • Propanolamines / analysis
  • Spectrometry, Mass, Fast Atom Bombardment / methods*

Substances

  • Arachidonic Acids
  • Cannabinoid Receptor Modulators
  • Endocannabinoids
  • Ethanolamines
  • Fatty Acids, Unsaturated
  • Polyunsaturated Alkamides
  • Propanolamines
  • Lithium
  • anandamide