Synthesis and characterization of glucuronides of cannabinol, cannabidiol, Δ9-tetrahydrocannabinol and Δ8-tetrahydrocannabinol

Authors

  • Michael A. Lyle,

    1. The Johns Hopkins University School of Medicine, Department of Pharmacology and Experimental Therapeutics, Baltimore, Maryland 21205, U.S.A.
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  • Sharon Pallante,

    1. The Johns Hopkins University School of Medicine, Department of Pharmacology and Experimental Therapeutics, Baltimore, Maryland 21205, U.S.A.
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  • Ken Head,

    1. The Johns Hopkins University School of Medicine, Department of Pharmacology and Experimental Therapeutics, Baltimore, Maryland 21205, U.S.A.
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  • Catherine Fenselau

    1. The Johns Hopkins University School of Medicine, Department of Pharmacology and Experimental Therapeutics, Baltimore, Maryland 21205, U.S.A.
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  • Abbreviations: THC = tetrahydrocannabinol; UDPG = uridine diphosphoglucuronyl.

Abstract

Partially purified glucuronyltransferase immobilized on beaded sepharose has been used to synthesize the glucuronide conjugates of cannabidol, cannabidol, Δ9-tetrahydrocannabinol and Δ8-tetrahydrocannabinol. Trimethylsilylated methyl esters and per(trimethylsilyl) derivatives of these conjugates have been characterized by their gas chromatographic retention times and their electron impact and ammonia chemical ionization mass spectra.

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