m-Hydroxybenzoylecgonine

An important contributor to the immunoreactivity in assays for benzoylecgonine in meconium

Bernard W Steele, Emmalee S Bandstra, N. C. Wu, G. W. Hime, W. L. Hearn

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

Meconium has been reported to be a more suitable specimen than maternal or neonatal urine for detecting fetal exposure to cocaine. In a study comparing various immunoassays with gas chromatography/mass spectrometry (GC/MS), several unexplained discrepancies among the assays were noted. Using methanol extracts of meconium samples, an immunoreactive spot that was more polar than benzoylecgonine was detected by thin-layer chromatography (TLC). An extract of this spot analyzed by GC/MS yielded a fragmentation pattern indicative of an aryl hydroxylated benzoylecgonine. Standards of m-hydroxybenzoylecgonine, o-hydroxybenzoylecgonine, and p-hydroxybenzoylecgonine were synthesized; it was determined that m-hydroxybenzoylecgonine had the same retention time and ion ratios as the TLC immunoreactive spot. Furthermore, m- hydroxybenzoylecgonine proved to be immunoreactive. Ten meconium samples immunoreactive for benzoylecgonine were analyzed by GC/MS. Results before and after hydrolysis with β-glucuronidase (type IX) showed free m- hydroxybenzoylecgonine comprising 59 to 94% of the total m- hydroxybenzoylecgonine and showed total m-hydroxybenzoylecgonine values ranging from 0.2 to 6.3 times as high as benzoylecgonine. Therefore, m- hydroxybenzoylecgonine appears to be a quantitatively important cocaine metabolite in meconium, which is responsible for a significant portion of the discrepancy between benzoylecgonine concentrations in meconium extracts as measured by immunoassay and GC/MS.

Original languageEnglish
Pages (from-to)348-352
Number of pages5
JournalJournal of Analytical Toxicology
Volume17
Issue number6
StatePublished - Jan 1 1993

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Meconium
Gas chromatography
Mass spectrometry
Assays
gas chromatography
mass spectrometry
assay
Thin layer chromatography
immunoassay
Gas Chromatography-Mass Spectrometry
chromatography
Thin Layer Chromatography
Metabolites
Cocaine
Immunoassay
urine
methanol
hydrolysis
Hydrolysis
metabolite

ASJC Scopus subject areas

  • Analytical Chemistry
  • Health, Toxicology and Mutagenesis
  • Toxicology

Cite this

m-Hydroxybenzoylecgonine : An important contributor to the immunoreactivity in assays for benzoylecgonine in meconium. / Steele, Bernard W; Bandstra, Emmalee S; Wu, N. C.; Hime, G. W.; Hearn, W. L.

In: Journal of Analytical Toxicology, Vol. 17, No. 6, 01.01.1993, p. 348-352.

Research output: Contribution to journalArticle

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