Emergence of the less common cannabinoid Δ8 -Tetrahydrocannabinol in a doping sample

Research output: Contribution to journalResearch articleContributedpeer-review

Contributors

  • Sebastian Rzeppa - , Institute of Doping Analysis and Sports Biochemistry Dresden (Author)
  • Joachim Große - , Institute of Doping Analysis and Sports Biochemistry Dresden (Author)
  • Claudia Rautenberg - , Institute of Doping Analysis and Sports Biochemistry Dresden (Author)
  • Detlef Thieme - , Institute of Doping Analysis and Sports Biochemistry Dresden (Author)
  • Triin Lepp - , Estonian Center for Integrity in Sports (Author)
  • Henn Vallimäe - , Estonian Center for Integrity in Sports (Author)
  • Annekathrin M Keiler - , Environmental Monitoring and Endocrinology (Research Group), Institute of Doping Analysis and Sports Biochemistry Dresden (Last author)

Abstract

Δ8 -Tetrahydrocannabinol (Δ8 -THC) as isomer of the well-known Δ9 -THC has a similar mode of action, and the potency was estimated to be two thirds compared with Δ9 -THC. Content of Δ8 -THC in plant material is low, but formulations containing Δ8 -THC in high concentrations are gaining popularity. Δ8 -THC is to be regarded as prohibited substance according to the Prohibited List of the World Anti-Doping Agency (WADA). Contradictory results between initial testing procedure and confirmatory quantitation for 11-Nor-9-carboxy-Δ9 -tetrahydrocannabinol (Δ9 -THC-COOH) of a doping control sample gave rise for follow-up testing procedures. After alkaline hydrolysis and liquid-liquid extraction, the sample was analyzed by high-performance liquid chromatography tandem mass spectrometry (HPLC-MS/MS) using isocratic elution instead of gradient elution, which is used for standard procedure. Isocratic elution resulted in two peaks instead of one using gradient elution. Both peaks showed same fragmentation. Using certified reference materials, one peak could be assigned to Δ9 -THC-COOH and the other one with higher intensity to the less common 11-Nor-9-carboxy-Δ8 -Tetrahydrocannabinol (Δ8 -THC-COOH) in a concentration of approximately 1200 ng/ml. As complementary method, gas chromatography tandem mass spectrometry (GC-MS/MS) can also be used for identification. Here Δ8 - and Δ9 -THC-COOH can be distinguished by chromatography and by fragmentation. Additional investigations of doping control samples containing Δ9 -THC-COOH revealed the simultaneous presence of Δ8 -THC-COOH in low concentrations (0.22-8.91 ng/ml) presumably due to plant origin. Percentage of Δ8 -THC-COOH varies from 0.05 to 2.83%. In vitro experiments using human liver microsomes showed that Δ8 -THC is metabolized in the same way as Δ9 -THC.

Details

Original languageEnglish
Pages (from-to)1936-1943
Number of pages8
JournalDrug testing and analysis
Volume13
Issue number11-12
Publication statusPublished - Nov 2021
Peer-reviewedYes

External IDs

Scopus 85115108896
ORCID /0000-0002-2157-4711/work/142251649

Keywords

Library keywords