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    Human hepatocyte metabolism of novel synthetic cannabinoids MN-18 and its 5-fluoro analog 5F-MN-18

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    Author
    Diao, X.
    Carlier, J.
    Zhu, M.
    Date
    2017
    Journal
    Clinical Chemistry
    Publisher
    American Association for Clinical Chemistry Inc.
    Type
    Article
    
    Metadata
    Show full item record
    See at
    https://doi.org/10.1373/clinchem.2017.277152
    Abstract
    BACKGROUND: In 2014, 2 novel synthetic cannabinoids, MN-18 and its 5-fluoro analog, 5F-MN-18, were first identified in an ongoing survey of novel psychoactive substances in Japan. In vitro pharmacological assays revealed that MN-18 and 5F-MN-18 displayed high binding affinities to human CB1 and CB2 receptors, with Ki being 1.65- 3.86 nmol/L. MN-18 and 5F-MN-18 were scheduled in Japan and some other countries in 2014. Despite increasing prevalence, no human metabolism data are currently available, making it challenging for forensic laboratories to confirm intake of MN-18 or 5F-MN-18. METHODS: We incubated 10 ?mol/L of MN-18 and 5F-MN-18 in human hepatocytes for 3 h and analyzed the samples on a TripleTOF 5600+ high-resolution mass spectrometer to identify appropriate marker metabolites. Data were acquired via full scan and informationdependent acquisition-triggered product ion scans with mass defect filter. RESULTS: In total, 13 MN-18 metabolites were detected, with the top 3 abundant metabolites being 1-pentyl-1Hindazole- 3-carboxylic acid, pentyl-carbonylated MN-18, and naphthalene-hydroxylated MN-18. For 5F-MN-18, 20 metabolites were observed, with the top 3 abundant metabolites being 5'-OH-MN-18, MN-18 pentanoic acid, and 1-(5-fluoropentyl)-1H-indazole-3-carboxylic acid. CONCLUSIONS: We have characterized MN-18 and 5FMN- 18 metabolism with human hepatocytes and highresolution mass spectrometry, and we recommend characteristic major metabolites for clinical and forensic laboratories to identify MN-18 and 5F-MN-18 intake and link observed adverse events to these novel synthetic cannabinoids.
    Keyword
    1-Naphthylamine--analogs & derivatives
    Cannabinoids--metabolism
    Fluorine--chemistry
    Hepatocytes--metabolism
    Indazoles--metabolism
    Identifier to cite or link to this item
    https://www.scopus.com/inward/record.uri?eid=2-s2.0-85032978389&doi=10.1373%2fclinchem.2017.277152&partnerID=40&md5=eb7b35660f8aeb8e06de5123d06380c3; http://hdl.handle.net/10713/11120
    ae974a485f413a2113503eed53cd6c53
    10.1373/clinchem.2017.277152
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    UMB Open Access Articles 2017

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