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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.
Forensic Sci Int 2010; 196(1-3):78-84FS

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.

Authors+Show Affiliations

Institute of Legal Medicine, University Hospital Charité, Hittorfstr. 18, 14195 Berlin, Germany.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

20074877

Citation

Nadulski, Thomas, et al. "11-nor-Delta9-tetrahydrocannabinol-9-carboxylic Acid Ethyl Ester (THC-COOEt): Unsuccessful Search for a Marker of Combined Cannabis and Alcohol Consumption." Forensic Science International, vol. 196, no. 1-3, 2010, pp. 78-84.
Nadulski T, Bleeck S, Schräder J, et al. 11-nor-Delta9-tetrahydrocannabinol-9-carboxylic acid ethyl ester (THC-COOEt): unsuccessful search for a marker of combined cannabis and alcohol consumption. Forensic Sci Int. 2010;196(1-3):78-84.
Nadulski, T., Bleeck, S., Schräder, J., Bork, W. R., & Pragst, F. (2010). 11-nor-Delta9-tetrahydrocannabinol-9-carboxylic acid ethyl ester (THC-COOEt): unsuccessful search for a marker of combined cannabis and alcohol consumption. Forensic Science International, 196(1-3), pp. 78-84. doi:10.1016/j.forsciint.2009.12.026.
Nadulski T, et al. 11-nor-Delta9-tetrahydrocannabinol-9-carboxylic Acid Ethyl Ester (THC-COOEt): Unsuccessful Search for a Marker of Combined Cannabis and Alcohol Consumption. Forensic Sci Int. 2010 Mar 20;196(1-3):78-84. PubMed PMID: 20074877.
* Article titles in AMA citation format should be in sentence-case
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 DB - PRIME DP - Unbound Medicine ER -