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Strategies to distinguish new synthetic cannabinoid FUBIMINA (BIM-2201) intake from its isomer THJ-2201: metabolism of FUBIMINA in human hepatocytes
NIDA, USA.
NIDA, USA.
Linköping University, Department of Medical and Health Sciences, Division of Drug Research. Linköping University, Faculty of Medicine and Health Sciences. National Board Forens Med, Department Forens Genet and Forens Toxicol, S-58758 Linkoping, Sweden.
Bristol Myers Squibb, NJ 08543 USA.
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2016 (English)In: Forensic Toxicology, ISSN 1860-8965, E-ISSN 1860-8973, Vol. 34, no 2, 256-267 p.Article in journal (Refereed) PublishedText
Abstract [en]

Since 2013, a new drugs-of-abuse trend attempts to bypass drug legislation by marketing isomers of scheduled synthetic cannabinoids (SCs), e.g., FUBIMINA (BIM-2201) and THJ-2201. It is much more challenging to confirm a specific isomers intake and distinguish it from its structural analog because the isomers and their major metabolites usually have identical molecular weights and display the same product ions. Here, we investigated isomers FUBIMINA and THJ-2201 and propose strategies to distinguish their consumption. THJ-2201 was scheduled in the US, Japan, and Europe; however, FUBIMINA is easily available on the Internet. We previously investigated THJ-2201 metabolism in human hepatocytes, but human FUBIMINA metabolism is unknown. We aim to characterize FUBIMINA metabolism in human hepatocytes, recommend optimal metabolites to confirm its consumption, and propose strategies to distinguish between intakes of FUBIMINA and THJ-2201. FUBIMINA (10 mu M) was incubated in human hepatocytes for 3 h, and metabolites were characterized with high-resolution mass spectrometry (HR-MS). We identified 35 metabolites generated by oxidative defluorination, further carboxylation, hydroxylation, dihydrodiol formation, glucuronidation, and their combinations. We recommend 5-OH-BIM-018 (M34), BIM-018 pentanoic acid (M33), and BIM-018 pentanoic acid dihydrodiol (M7) as FUBIMINA specific metabolites. THJ-2201 produced specific metabolite markers 5-OH-THJ-018 (F26), THJ-018 pentanoic acid (F25), and hydroxylated THJ-2201 (F13). Optimized chromatographic conditions to achieve different retention times and careful selection of specific product ion spectra enabled differentiation of isomeric metabolites, in this case FUBIMINA from THJ-2201. Our HR-MS approach should be applicable for differentiating future isomeric SCs, which is especially important when different isomers have different legal status.

Place, publisher, year, edition, pages
SPRINGER , 2016. Vol. 34, no 2, 256-267 p.
Keyword [en]
FUBIMINA; BIM-2201; THJ-2201; Synthetic cannabinoid; Hepatocyte metabolism; Isomer
National Category
Pharmaceutical Sciences
Identifiers
URN: urn:nbn:se:liu:diva-130419DOI: 10.1007/s11419-016-0312-2ISI: 000379164800006OAI: oai:DiVA.org:liu-130419DiVA: diva2:952647
Note

Funding Agencies|Intramural Research Program of the National Institute on Drug Abuse, National Institutes of Health

Available from: 2016-08-15 Created: 2016-08-05 Last updated: 2016-08-22

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Wohlfarth, Ariane
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