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Sensitive, rapid and validated gas chromatography/negative ion chemical ionization-mass spectrometry assay including derivatisation with a novel chiral agent for the enantioselective quantification of amphetamine-type stimulants in hair.
J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Oct 02; 842(2):98-105.JC

Abstract

A novel chiral derivatisation agent, (2S,4R)-N-heptafluorobutyryl-4-heptafluorobutoyloxy-prolyl chloride, was used for the indirect resolution of amphetamine (AM), methamphetamine (MA), 3,4-methylenedioxyamphetamine (MDA), 3,4-methylenedioxymethamphetamine (MDMA) and 3,4-methylenedioxyethylamphetamine (MDEA) enantiomers using gas chromatography coupled to mass spectrometry operating in the negative-ion chemical ionization mode (GC/MS-NICI). This new chiral derivatisation reagent was readily obtained in optically pure form after a simple two-step synthesis. Optimal derivatisation was accomplished in 15 min at room temperature in a carbonate buffer and the resulting diastereoisomers were base line separated by GC in 12 min only. No racemization was observed during the derivatisation. The method was applied and fully validated for the enantiomeric quantification of amphetamines and methylenedioxylated amphetamines in hair. The analyses of 24 hair specimens from suspected ATS abusers showed that 24 cases were positive for MA and/or AM enantiomers and that in most cases the concentrations of (S)-MA and (S)-AM exceeded those of the corresponding (R)-enantiomers. One hair specimen was tested positive for both enantiomers of MDMA and MDA.

Authors+Show Affiliations

National Laboratory of Health, Toxicology Division, University of Luxembourg, 162A avenue de la Faïencerie, L-1511 Luxembourg, Luxembourg. liliane.martins@uni.luNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

16714155

Citation

Martins, Liliane Ferreira, et al. "Sensitive, Rapid and Validated Gas Chromatography/negative Ion Chemical Ionization-mass Spectrometry Assay Including Derivatisation With a Novel Chiral Agent for the Enantioselective Quantification of Amphetamine-type Stimulants in Hair." Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences, vol. 842, no. 2, 2006, pp. 98-105.
Martins LF, Yegles M, Chung H, et al. Sensitive, rapid and validated gas chromatography/negative ion chemical ionization-mass spectrometry assay including derivatisation with a novel chiral agent for the enantioselective quantification of amphetamine-type stimulants in hair. J Chromatogr B Analyt Technol Biomed Life Sci. 2006;842(2):98-105.
Martins, L. F., Yegles, M., Chung, H., & Wennig, R. (2006). Sensitive, rapid and validated gas chromatography/negative ion chemical ionization-mass spectrometry assay including derivatisation with a novel chiral agent for the enantioselective quantification of amphetamine-type stimulants in hair. Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences, 842(2), 98-105.
Martins LF, et al. Sensitive, Rapid and Validated Gas Chromatography/negative Ion Chemical Ionization-mass Spectrometry Assay Including Derivatisation With a Novel Chiral Agent for the Enantioselective Quantification of Amphetamine-type Stimulants in Hair. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Oct 2;842(2):98-105. PubMed PMID: 16714155.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Sensitive, rapid and validated gas chromatography/negative ion chemical ionization-mass spectrometry assay including derivatisation with a novel chiral agent for the enantioselective quantification of amphetamine-type stimulants in hair. AU - Martins,Liliane Ferreira, AU - Yegles,Michel, AU - Chung,Heesun, AU - Wennig,Robert, Y1 - 2006/05/22/ PY - 2005/12/16/received PY - 2006/04/12/revised PY - 2006/04/14/accepted PY - 2006/5/23/pubmed PY - 2006/12/23/medline PY - 2006/5/23/entrez SP - 98 EP - 105 JF - Journal of chromatography. B, Analytical technologies in the biomedical and life sciences JO - J Chromatogr B Analyt Technol Biomed Life Sci VL - 842 IS - 2 N2 - A novel chiral derivatisation agent, (2S,4R)-N-heptafluorobutyryl-4-heptafluorobutoyloxy-prolyl chloride, was used for the indirect resolution of amphetamine (AM), methamphetamine (MA), 3,4-methylenedioxyamphetamine (MDA), 3,4-methylenedioxymethamphetamine (MDMA) and 3,4-methylenedioxyethylamphetamine (MDEA) enantiomers using gas chromatography coupled to mass spectrometry operating in the negative-ion chemical ionization mode (GC/MS-NICI). This new chiral derivatisation reagent was readily obtained in optically pure form after a simple two-step synthesis. Optimal derivatisation was accomplished in 15 min at room temperature in a carbonate buffer and the resulting diastereoisomers were base line separated by GC in 12 min only. No racemization was observed during the derivatisation. The method was applied and fully validated for the enantiomeric quantification of amphetamines and methylenedioxylated amphetamines in hair. The analyses of 24 hair specimens from suspected ATS abusers showed that 24 cases were positive for MA and/or AM enantiomers and that in most cases the concentrations of (S)-MA and (S)-AM exceeded those of the corresponding (R)-enantiomers. One hair specimen was tested positive for both enantiomers of MDMA and MDA. SN - 1570-0232 UR - https://www.unboundmedicine.com/medline/citation/16714155/Sensitive_rapid_and_validated_gas_chromatography/negative_ion_chemical_ionization_mass_spectrometry_assay_including_derivatisation_with_a_novel_chiral_agent_for_the_enantioselective_quantification_of_amphetamine_type_stimulants_in_hair_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S1570-0232(06)00348-5 DB - PRIME DP - Unbound Medicine ER -