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Electron ionization mass fragmentometric detection of urinary ecgonidine, a hydrolytic product of methylecgonidine, as an indicator of smoking cocaine.
J Mass Spectrom. 1999 Jun; 34(6):651-60.JM

Abstract

When cocaine is smoked, methylecgonidine (anhydroecgonine methyl ester) is also consumed as a pyrolytic product. Methylecgonidine, on incubation with human liver homogenate, was metabolized to a stable compound, ecgonidine. The compound was also formed when methylecgonidine was exposed to a urine pH > or = 8.0. Ecgonidine is a zwitterion and highly water soluble. A method was developed to identify ecgonidine quantitatively in urine. After removal of cocaine, benzoylecgonine and methylecgonidine from urine at pH 5.5 +/- 0.5 using a solid-phase extraction (SPE) technique, the pH of the solution was readjusted to 2.0-3.0. The acidic solution reduced the dissociation of the carboxylic acid and improved the lipophilic and cationic character of ecgonidine. The compound was extracted from the solution with the SPE technique with an 89-99% yield. Ecgonidine was then detected as a tert-butyldimethylsilyl derivative by a gas chromatographic/electron ionization mass spectrometric method. Quantitation was linear over the concentration range 7-2000 ng ml-1. Concentrations as low as 7 ng ml-1 can be detected by this procedure. Ecgonidine was detected in > 95% of benzoylecgonine-positive urine specimens from a random drug testing program, indicating smoking as the major route of cocaine administration.

Authors+Show Affiliations

Division of Forensic Toxicology, Office of the Armed Forces Medical Examiner, Armed Forces Institute of Pathology, Rockville, Maryland 20850, USA. paul@afip.osd.milNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

10394630

Citation

Paul, B D., et al. "Electron Ionization Mass Fragmentometric Detection of Urinary Ecgonidine, a Hydrolytic Product of Methylecgonidine, as an Indicator of Smoking Cocaine." Journal of Mass Spectrometry : JMS, vol. 34, no. 6, 1999, pp. 651-60.
Paul BD, McWhorter LK, Smith ML. Electron ionization mass fragmentometric detection of urinary ecgonidine, a hydrolytic product of methylecgonidine, as an indicator of smoking cocaine. J Mass Spectrom. 1999;34(6):651-60.
Paul, B. D., McWhorter, L. K., & Smith, M. L. (1999). Electron ionization mass fragmentometric detection of urinary ecgonidine, a hydrolytic product of methylecgonidine, as an indicator of smoking cocaine. Journal of Mass Spectrometry : JMS, 34(6), 651-60.
Paul BD, McWhorter LK, Smith ML. Electron Ionization Mass Fragmentometric Detection of Urinary Ecgonidine, a Hydrolytic Product of Methylecgonidine, as an Indicator of Smoking Cocaine. J Mass Spectrom. 1999;34(6):651-60. PubMed PMID: 10394630.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Electron ionization mass fragmentometric detection of urinary ecgonidine, a hydrolytic product of methylecgonidine, as an indicator of smoking cocaine. AU - Paul,B D, AU - McWhorter,L K, AU - Smith,M L, PY - 1999/7/8/pubmed PY - 2000/6/22/medline PY - 1999/7/8/entrez SP - 651 EP - 60 JF - Journal of mass spectrometry : JMS JO - J Mass Spectrom VL - 34 IS - 6 N2 - When cocaine is smoked, methylecgonidine (anhydroecgonine methyl ester) is also consumed as a pyrolytic product. Methylecgonidine, on incubation with human liver homogenate, was metabolized to a stable compound, ecgonidine. The compound was also formed when methylecgonidine was exposed to a urine pH > or = 8.0. Ecgonidine is a zwitterion and highly water soluble. A method was developed to identify ecgonidine quantitatively in urine. After removal of cocaine, benzoylecgonine and methylecgonidine from urine at pH 5.5 +/- 0.5 using a solid-phase extraction (SPE) technique, the pH of the solution was readjusted to 2.0-3.0. The acidic solution reduced the dissociation of the carboxylic acid and improved the lipophilic and cationic character of ecgonidine. The compound was extracted from the solution with the SPE technique with an 89-99% yield. Ecgonidine was then detected as a tert-butyldimethylsilyl derivative by a gas chromatographic/electron ionization mass spectrometric method. Quantitation was linear over the concentration range 7-2000 ng ml-1. Concentrations as low as 7 ng ml-1 can be detected by this procedure. Ecgonidine was detected in > 95% of benzoylecgonine-positive urine specimens from a random drug testing program, indicating smoking as the major route of cocaine administration. SN - 1076-5174 UR - https://www.unboundmedicine.com/medline/citation/10394630/Electron_ionization_mass_fragmentometric_detection_of_urinary_ecgonidine_a_hydrolytic_product_of_methylecgonidine_as_an_indicator_of_smoking_cocaine_ L2 - https://doi.org/10.1002/(SICI)1096-9888(199906)34:6<651::AID-JMS817>3.0.CO;2-M DB - PRIME DP - Unbound Medicine ER -