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Detection in seized...
Detection in seized samples, analytical characterization, and in vitro metabolism of the newly emerged 5-bromo-indazole-3-carboxamide synthetic cannabinoid receptor agonists
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- Norman, Caitlyn (author)
- Univ Dundee, Scotland
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- Webling, Kristin (author)
- Linköpings universitet,Avdelningen för klinisk kemi och farmakologi,Medicinska fakulteten
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- Kyslychenko, Oleksandra (author)
- Linköpings universitet,Avdelningen för klinisk kemi och farmakologi,Medicinska fakulteten
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- Reid, Robert (author)
- Univ Dundee, Scotland
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- Krotulski, Alex J. (author)
- Fredric Rieders Family Fdn, PA USA
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- Farrell, Ryan (author)
- Indianapolis Marion Cty Forens Serv Agcy, IN USA
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- Deventer, Marie H. (author)
- Univ Ghent, Belgium
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- Liu, Huiling (author)
- Chiron AS, Norway
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- Connolly, Matthew J. (author)
- Chiron AS, Norway
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- Guillou, Claude (author)
- European Commiss, Italy
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- Vinckier, Inge M. J. (author)
- Lab Customs & Excises, Belgium
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- Logan, Barry K. (author)
- Fredric Rieders Family Fdn, PA USA; NMS Labs, PA USA
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- NicDaeid, Niamh (author)
- Univ Dundee, Scotland
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- McKenzie, Craig (author)
- Univ Dundee, Scotland; Chiron AS, Norway
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- Stove, Christophe P. (author)
- Univ Ghent, Belgium
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- Green, Henrik (author)
- Linköpings universitet,Avdelningen för klinisk kemi och farmakologi,Medicinska fakulteten,Natl Board Forens Med, Dept Forens Genet & Forens Toxicol, Linkoping, Sweden
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(creator_code:org_t)
- 2023
- 2023
- English.
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In: Drug Testing and Analysis. - : WILEY. - 1942-7603 .- 1942-7611.
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
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- Synthetic cannabinoid receptor agonists (SCRAs) are a diverse class of new psychoactive substances (NPS) and new structural scaffolds have emerged on the recreational drug market since the enactment of Chinese SCRA analog controls in 2021. This study reports the first SCRAs to be detected with a bromide at the 5 position (5 ' Br) on the phenyl ring of the indazole core and without a tail moiety. ADB-5 ' Br-INACA (ADMB-5 ' Br-INACA) and MDMB-5 ' Br-INACA were detected in seized samples from Scottish prisons, Belgian customs, and US forensic casework. The brominated analog with a tail moiety, ADB-5 ' Br-BUTINACA (ADMB-5 ' Br-BUTINACA), was also detected in Scottish prisons and US forensic casework. The metabolites of these compounds and the predicted compound MDMB-5 ' Br-BUTINACA were identified through incubation with primary human hepatocytes to aid in their toxicological identification. The bromide on the indazole remains intact on metabolites, allowing these compounds to be easily distinguished in toxicological samples from their non-brominated analogs. Glucuronidation was more common for tail-less analogs than their butyl tail-containing counterparts. Forensic toxicologists are advised to update their analytical methods with the characteristic ions for these compounds, as well as their anticipated urinary markers: amide hydrolysis and monoOH at tert-butyl metabolites (after beta-glucuronidase treatment) for ADB-5 ' Br-INACA; monoOH at tert-butyl and amide hydrolysis metabolites for ADB-5 ' Br-BUTINACA; and ester hydrolysis metabolites with additional metabolites for MDMB-5 ' Br-INACA and MDMB-5 ' Br-BUTINACA. Toxicologists should remain vigilant to the emergence of new SCRAs with halogenation of the indazole core and tail-less analogs, which have already started to emerge. This study reports the detection of the new synthetic cannabinoids ADB-5 ' Br-INACA and MDMB-5 ' Br-INACA in Scotland, Belgium, and the US, and ADB-5 ' Br-BUTINACA in Scotland and the US. These compounds, along with the predicted compound MDMB-5 ' Br-BUTINACA, were incubated with primary human hepatocytes to examine metabolic pathways and aid in toxicological identification.image
Subject headings
- MEDICIN OCH HÄLSOVETENSKAP -- Medicinska och farmaceutiska grundvetenskaper -- Läkemedelskemi (hsv//swe)
- MEDICAL AND HEALTH SCIENCES -- Basic Medicine -- Medicinal Chemistry (hsv//eng)
Keyword
- brominated synthetic cannabinoid receptor agonists; forensic toxicology; metabolism; new psychoactive substances; prison seizures
Publication and Content Type
- ref (subject category)
- art (subject category)
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- By the author/editor
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Norman, Caitlyn
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Webling, Kristin
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Kyslychenko, Ole ...
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Reid, Robert
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Krotulski, Alex ...
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Farrell, Ryan
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Deventer, Marie ...
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Liu, Huiling
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Connolly, Matthe ...
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Guillou, Claude
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Vinckier, Inge M ...
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Logan, Barry K.
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NicDaeid, Niamh
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McKenzie, Craig
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Stove, Christoph ...
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Green, Henrik
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- About the subject
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- MEDICAL AND HEALTH SCIENCES
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MEDICAL AND HEAL ...
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and Basic Medicine
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and Medicinal Chemis ...
- Articles in the publication
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Drug Testing and ...
- By the university
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Linköping University