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Detection and phase I metabolism of the 7-azaindole-derived synthetic cannabinoid 5F-AB-P7AICA including a preliminary pharmacokinetic evaluation.

A. Giorgetti,Lukas Mogler,B. Haschimi,S. Halter,F. Franz,F. Westphal,Svenja Fischmann,Jan Riedel,M. Pütz,V. Auwärter

Published 2019 in Drug Testing and Analysis

ABSTRACT

In June 2018, a 'research chemical' labelled 'AB-FUB7AICA' was purchased online and analytically identified as 5F-AB-P7AICA, the 7-azaindole analog of 5F-AB-PINACA. Here we present data on structural characterization, suitable urinary consumption markers and preliminary pharmacokinetic data. Structure characterization was performed by nuclear magnetic resonance spectroscopy, gas chromatography-mass spectrometry, infrared and raman spectroscopy. Phase I metabolites were generated by applying a pooled human liver microsome assay (pHLM) to confirm the analysis results of authentic urine samples collected after oral self-administration of 2.5 mg 5F-AB-P7AICA. Analyses of pHLM and urine samples were performed by liquid chromatography-time-of-flight mass spectrometry and liquid chromatography-tandem mass spectrometry (LC-MS/MS). An LC-MS/MS method for the quantification of 5F-AB-P7AICA in serum was validated. Ten phase I metabolites were detected in human urine samples and confirmed in vitro. The main metabolites were formed by hydroxylation, amide hydrolysis and hydrolytic defluorination, though - in contrast to most other synthetic cannabinoids - the parent compound showed the highest signals in most urine samples. The compound detection window was more than 45 h in serum. The concentration-time profile was best explained by a two phase pharmacokinetic model. 5F-AB-P7AICA was detected in urine samples until 65h post ingestion. Monitoring of metabolite M07, hydroxylated at the alkyl chain, next to parent 5F-AB-P7AICA, is recommended to confirm the uptake of 5F-AB-P7AICA in urinalysis. It seems plausible that the shift of the nitrogen atom from position 2 to 7 (e.g. 5F-AB-PINACA to 5F-AB-P7AICA) leads to a lower metabolic reactivity, which might be of general interest in medicinal chemistry.

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