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11-nor-Delta9-tetrahydrocannabinol-9-carboxylic acid ethyl ester (THC-COOEt): unsuccessful search for a marker of combined cannabis and alcohol consumption.

Abstract

11-Nor-Delta(9)-tetrahydrocannabinol-9-carboxylic acid ethyl ester (THC-COOEt) can be presumed to be a mixed metabolite formed during combined consumption of cannabinoids and alcohol. In order to examine this hypothesis, THC-COOEt and its deuterated analogue D(3)-THC-COOEt were synthesized as reference substance and internal standard from the corresponding carboxylic acids and diazoethane and methods were developed for the sensitive detection of THC-COOEt in plasma and hair based on gas chromatography-electron impact mass spectrometry after silylation with N-methyl-N-tert-butyldimethylsilyl-trifluoroacetamide and gas chromatography-negative chemical ionization mass spectrometry (GC-NCI-MS) as well as tandem mass spectrometry (GC-NCI-MS-MS) after derivatization with pentafluoropropionyl anhydride. The methods were applied for THC-COOEt determination to plasma samples from 22 drunk driving cases which contained both ethanol (0.30-2.16 mg/g) and THC-COOH (15-252 ng/mL) as well as to 12 hair samples from drug fatalities which were both positive for THC (0.09-2.04 ng/mg) and fatty acid ethyl esters as markers of chronic alcohol abuse (0.70-6.3 ng/mg). In none of these samples THC-COOEt could be found with limits of detection of 0.3 ng/mL in plasma and 2 pg/mg in hair in 11 samples using GC-NCI-MS and 0.2 pg/mg in one sample using GC-NCI-MS. Therefore, the use of this compound as a marker for combined cannabis and alcohol consumption could not be achieved.

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  • Publisher Full Text
  • Authors+Show Affiliations

    ,

    Institute of Legal Medicine, University Hospital Charité, Hittorfstr. 18, 14195 Berlin, Germany.

    , , ,

    Source

    Forensic science international 196:1-3 2010 Mar 20 pg 78-84

    MeSH

    Alcohol Drinking
    Alcoholism
    Biomarkers
    Central Nervous System Depressants
    Dronabinol
    Ethanol
    Fatty Acids
    Forensic Toxicology
    Gas Chromatography-Mass Spectrometry
    Hair
    Hallucinogens
    Humans
    Marijuana Smoking
    Substance Abuse Detection

    Pub Type(s)

    Journal Article

    Language

    eng

    PubMed ID

    20074877

    Citation

    TY - JOUR T1 - 11-nor-Delta9-tetrahydrocannabinol-9-carboxylic acid ethyl ester (THC-COOEt): unsuccessful search for a marker of combined cannabis and alcohol consumption. AU - Nadulski,Thomas, AU - Bleeck,Simona, AU - Schräder,Johannes, AU - Bork,Wolf-Rainer, AU - Pragst,Fritz, Y1 - 2010/01/13/ PY - 2009/07/13/received PY - 2009/07/20/accepted PY - 2010/1/16/entrez PY - 2010/1/16/pubmed PY - 2010/6/11/medline SP - 78 EP - 84 JF - Forensic science international JO - Forensic Sci. Int. VL - 196 IS - 1-3 N2 - 11-Nor-Delta(9)-tetrahydrocannabinol-9-carboxylic acid ethyl ester (THC-COOEt) can be presumed to be a mixed metabolite formed during combined consumption of cannabinoids and alcohol. In order to examine this hypothesis, THC-COOEt and its deuterated analogue D(3)-THC-COOEt were synthesized as reference substance and internal standard from the corresponding carboxylic acids and diazoethane and methods were developed for the sensitive detection of THC-COOEt in plasma and hair based on gas chromatography-electron impact mass spectrometry after silylation with N-methyl-N-tert-butyldimethylsilyl-trifluoroacetamide and gas chromatography-negative chemical ionization mass spectrometry (GC-NCI-MS) as well as tandem mass spectrometry (GC-NCI-MS-MS) after derivatization with pentafluoropropionyl anhydride. The methods were applied for THC-COOEt determination to plasma samples from 22 drunk driving cases which contained both ethanol (0.30-2.16 mg/g) and THC-COOH (15-252 ng/mL) as well as to 12 hair samples from drug fatalities which were both positive for THC (0.09-2.04 ng/mg) and fatty acid ethyl esters as markers of chronic alcohol abuse (0.70-6.3 ng/mg). In none of these samples THC-COOEt could be found with limits of detection of 0.3 ng/mL in plasma and 2 pg/mg in hair in 11 samples using GC-NCI-MS and 0.2 pg/mg in one sample using GC-NCI-MS. Therefore, the use of this compound as a marker for combined cannabis and alcohol consumption could not be achieved. SN - 1872-6283 UR - https://www.unboundmedicine.com/medline/citation/20074877/abstract/11_nor_Delta9_tetrahydrocannabinol_9_carboxylic_acid_ethyl_ester__THC_COOEt_:_unsuccessful_search_for_a_marker_of_combined_cannabis_and_alcohol_consumption_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0379-0738(09)00527-1 ER -