Detection of metabolites of two synthetic cannabimimetics, MDMB-FUBINACA and ADB-FUBINACA, in authentic human urine specimens by accurate mass LC–MS: a comparison of intersecting metabolic patterns
| Autor: | Andrej Grigoryev, Pierce V. Kavanagh, Natalia Krupina |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Chromatography
010401 analytical chemistry Biochemistry (medical) Glucuronidation Toxicology 01 natural sciences 0104 chemical sciences Pathology and Forensic Medicine Hydroxylation 03 medical and health sciences chemistry.chemical_compound Metabolic pathway Hydrolysis 0302 clinical medicine chemistry Liquid chromatography–mass spectrometry Dihydroxylation Amide Synthetic cannabinoids medicine 030216 legal & forensic medicine medicine.drug |
| Zdroj: | Forensic Toxicology. 35:284-300 |
| ISSN: | 1860-8973 1860-8965 |
| DOI: | 10.1007/s11419-017-0356-y |
| Popis: | The structures of two indazole-derived synthetic cannabimimetics, a methyl ester, MDMB-FUBINACA, and an amide, ADB-FUBINACA, differ only in the terminal groups on the side chains. Based upon liquid chromatography–quadrupole time-of-flight-mass spectrometry analysis of urine and blood samples collected from patients who were admitted to hospital with suspected drug intoxications and from postmortem forensic investigations, 38 metabolites were tentatively identified. Hydrolysis of the terminal groups (methyl ester and amide for MDMB-FUBINACA and ADB-FUBINACA, respectively) was found to be a common metabolic pathway for both compounds, leading to the formation of other common metabolites. Hydrolysed metabolites undergo subsequent monohydroxylation, dihydrodiol formation, fluorobenzyl loss and dehydrogenation. Most of the metabolites of MDMB-FUBINACA were products of ester hydrolysis. Metabolites formed by hydrolysis, additional monohydroxylation, dihydrodiol formation and fluorobenzyl loss were also detected in forms of glucuronides. Two unhydrolysed metabolites were identified as products of hydroxylation and fluorobenzyl loss with subsequent glucuronidation. In the case of ADB-FUBINACA, products of mono- and dihydroxylation, dihydrodiol formation, dihydrodiol formation combined with monohydroxylation, monohydroxylation combined with dehydrogenation and fluorobenzyl loss with monohydroxylation were identified. Monohydroxylated and dihydrodiol metabolites were also detected in the form of glucuronides. The most abundant metabolites were products of ester hydrolysis in free and glucuronidated forms (for MDMB-FUBINACA) and of dihydrodiol formation (for ADB-FUBINACA). These compounds are recommended for toxicological screening. To our knowledge, there are no reports dealing with the detection of metabolites of MBDB-FUBINACA and ADB-FUBINACA in authentic human urine specimens. |
| Databáze: | OpenAIRE |
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