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Endocannabinoid metabolomics: A novel liquid chromatography-mass spectrometry reagent for fatty acid analysis

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Abstract

We have synthesized 4,4-dimethoxyoxazoline derivatives of several fatty acids associated with the endocannabinoid metabolome using tris(hydroxymethyl)aminomethane in a 1-step reaction by microwave irradiation. The derivatization incorporates a nitrogen into the final product, which allows for improved detection by liquid chromatographymass spectrometry in positive atmospheric pressure chemical ionization (APCI) mode. Palmitic and oleic acid derivatives show a 200-fold increase in sensitivity compared with the free acids when analyzed in negative-mode APCI. In addition to improving sensitivity, the oxazoline derivatization creates a similar ionization response for the fatty acids tested, which simplifies their quantitation. Fatty acid oxazoline derivatives can be detected using the same conditions optimized for the endocannabinoids, which allows for a simultaneous quantitation of the entire endocannabinoid metabolome.

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Authors and Affiliations

  1. Center for Drug Discovery, Northeastern University, Boston, MA

    John Williams, Lakshmipathi Pandarinathan, Jodi Anne Wood & Alexandros Makriyannis

  2. Barnett Institute and Department of Chemistry, Northeastern University, Boston, MA

    John Williams & Paul Vouros

Authors
  1. John Williams
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  2. Lakshmipathi Pandarinathan
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  3. Jodi Anne Wood
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  4. Paul Vouros
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  5. Alexandros Makriyannis
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Correspondence to Alexandros Makriyannis.

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Published: October 20, 2006

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Williams, J., Pandarinathan, L., Wood, J.A. et al. Endocannabinoid metabolomics: A novel liquid chromatography-mass spectrometry reagent for fatty acid analysis. AAPS J 8, 74 (2006). https://doi.org/10.1208/aapsj080474

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  • DOI: https://doi.org/10.1208/aapsj080474

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