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Detection and quantification of low concentrations of 11-nor-delta-9-tetrahydrocannabinol-9-carboxylic acid from minimal amounts of urine

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Summary

A simple liquid-liquid extraction and GC/MSmethod for detection and quantification of 11-nor-delta-9-tetrahydrocannabinol-9-carboxylic acid (THC-COOH) from merely 1 ml urine is described. The derivatisation to the methyl ester was carried out using methyl iodide and mefenamic acid was used as internal standard. Experiments with urine spiked with 15 ng THC-COOH/ml resulted in a recovery of 91%. Excellent linearity was obtained over the range 5–100 ng/ml.

Zusammenfassung

Eine leicht zu handhabende Flüssig-Flüssig-Extraktions-und GC/MS-Methodik zur Identifizierung und Quantifizierung der 11-Nor-Delta-9-Tetrahydrocannabinol-9-Carbonsäure (THC-COOH) aus lediglich 1 ml Urin wird beschrieben. Die Derivatisierung zum Methyl-Ester erfolgt durch den Einsatz von Jodmethan. Mefenaminsäure wird als interner Standard eingesetzt. Versuche mit gespiktem Urin führten zu einer Wiederfindungsrate von 91% bei 15 ng THC-COOH/ml Urin. Eine ausgezeichnete Linearität wurde über den Bereich von 5–100 ng/ml beobachtet.

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References

  1. ElSohly MA, ElSohly H, Jones AB, Dimson PA, Wells KE (1983) Analysis of the major metabolite of delta-9-tetrahydrocannabinol in urine. II. A HPLC procedure. J Anal Toxicol 7: 262–264

    PubMed  Google Scholar 

  2. ElSohly MA, Arafat ES, Jones AB (1984) Analysis of the major metabolite of delta-9-tetrahydrocannabinol in urine. III. A GC/ECD procedure. J Anal Toxicol 8: 7–9

    PubMed  Google Scholar 

  3. ElSohly MA, Stanford DF, Little TL Jr (1988)2H6-11-nor-delta-8-THC-9-COOH: a new internal standard for the analysis of THC metabolite in biological fluids. J Anal Toxicol 12: 54–55

    PubMed  Google Scholar 

  4. Karlsson L, Jonsson J, Åberg K, Roos C (1983) Determination of delta-9-tetrahydrocannabinol-11-oic acid in urine as its pentafluoropropyl-, pentafluoro-propionyl derivative by GC/ MS utilizing negative ion chemical ionization. J Anal Toxicol 7: 198–202

    PubMed  Google Scholar 

  5. Kiser RE, Ramsden HE, Patterson JM (1986) Solid phase extraction of delta-9-carboxy-THC from urine. Clin Chem 32: 1115

    Google Scholar 

  6. Kogan MJ, Newman E, Willson NJ (1984) Detection of marijuana metabolite 11-nor-delta-9-tetrahydrocannabinol-9carboxylic acid in human urine by bonded-phase adsorption and thin-layer chromatography. J Chromatogr 306: 441–443

    PubMed  Google Scholar 

  7. McCurdy HH, Lewellen LJ, Callahan LS, Childs PS (1986) Evaluation of the ion trap detector for the detection of 11-nordelta-9-THC-9-carboxylic acid in urine after extraction by bonded-phase adsorption. J Anal Toxicol 10: 175–177

    PubMed  Google Scholar 

  8. Nakamura GR, Meeks RD, Stall WJ (1990) Solid-phase extraction, identification, and quantitation of 11-nor-delta-9tetrahydrocannabinol-9-carboxylic acid. J Forensic Sci 35: 792–796

    PubMed  Google Scholar 

  9. Parry RP, Nolan L, Shirey RE, Wachob GD, Gisch DL (1990) Pretreatment of urine samples for the analysis of 11-nor-delta9-tetrahydrocannabinol-9-carboxylic acid using solid-phase extraction. J Anal Toxicol 14: 39–44

    PubMed  Google Scholar 

  10. Paul BD, Mell LD Jr, Mitchell JM, McKinley RM (1987) Detection and quantitation of urinary 11-nor-delta-9-tetrahydrocannabinol-9-carboxylic acid, a metabolite of tetrahydrocannabinol, by capillary gas chromatography and electron impact mass fragmentography. J Anal Toxicol 11: 1–5

    PubMed  Google Scholar 

  11. Peat MA, Deyman ME, Johnson JR (1984) High performance liquid chromatography-immunoassay of delta-9-tetrahydrocannabinol and its metabolites in urine. J Forensic Sci 29: 110–119

    PubMed  Google Scholar 

  12. TOXI-LAB Screening and confirmation of drugs of abuse (1987) Analytical Systems Division of Marion Laboratories, Irvine, CA

  13. Whiting JD, Manders WW (1982) Confirmation of a tetrahydrocannabinol metabolite in urine by gas chromatography. J Anal Toxicol 6: 49–52

    PubMed  Google Scholar 

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The results were reported at the 22. Jahrestagung des Nord- und Westdeutschen Arbeitskreises der Deutschen Gesellschaft für Rechtsmedizin, Hannover, April 26–27 1991 (Muβhoff and Daldrup, 48)

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Mußhoff, F., Daldrup, T. Detection and quantification of low concentrations of 11-nor-delta-9-tetrahydrocannabinol-9-carboxylic acid from minimal amounts of urine. Int J Leg Med 104, 263–266 (1991). https://doi.org/10.1007/BF01369582

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  • DOI: https://doi.org/10.1007/BF01369582

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