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Stereoselective method development and validation for determination of concentrations of amphetamine-type stimulants and metabolites in human urine using a simultaneous extraction-chiral derivatization approach.

Abstract

Amphetamine-type stimulants (ATS) are a group of chiral amine drugs which are commonly abused for their sympathomimetic and stimulant properties. ATS are extensively metabolised by hepatic cytochrome P450 enzymes. As metabolism of ATS has been shown to be highly stereospecific, stereoselective analytical methods are essential for the quantitative determination of ATS concentrations for both in vivo and in vitro studies of ATS metabolism. This paper describes a new stereoselective method for the simultaneous determination of amphetamine (AM), methamphetamine (MA), 3,4-methylenedioxymethamphetamine (MDMA), 3,4-methylenedioxyamphetamine (MDA), 4-hydroxy-3-methoxymethamphetamine (HMMA), 4-hydroxy-3-methoxyamphetamine (HMA), 3,4-hydroxymethamphetamine (HHMA) and 3,4-hydroxyamphetamine (HHA) in human urine samples validated according to the United States Food and Drug Administration guidelines. In this method, analytes are simultaneously extracted and derivatized with R-(-)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride (R-MTPCl) as the chiral derivatization reagent. Following this, the analytes were subjected to a second derivatization with N-methyl-N-trimethylsilyltrifluoroacetamide (MSTFA) which targets the hydroxyl groups present in HMMA, HMA, HHMA and HHA. The derivatized analytes were separated and quantified using gas chromatography-mass spectrometry (GC-MS). The method was evaluated according to the established guidelines for specificity, linearity, precision, accuracy, recovery and stability using a five-day protocol. Intra-day precision ranged from 0.89 to 11.23% RSD whereas inter-day precision was between 1.03 and 12.95% RSD. Accuracy values for the analytes ranged from -5.29% to 13.75%. Limits of quantitation were 10 μg/L for AM, MA, MDMA, HMA and HMMA and 2μg/L for MDA, HMA and HHA. Recoveries and stability values were also within accepted values. The method was applied to authentic ATS-positive samples.

Authors+Show Affiliations

Department of Pharmacology, School of Medical Sciences, Universiti Sains Malaysia, 16150 Kubang Kerian, Kelantan, Malaysia.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21147046

Citation

Wan Raihana, W A., et al. "Stereoselective Method Development and Validation for Determination of Concentrations of Amphetamine-type Stimulants and Metabolites in Human Urine Using a Simultaneous Extraction-chiral Derivatization Approach." Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences, vol. 879, no. 1, 2011, pp. 8-16.
Wan Raihana WA, Gan SH, Tan SC. Stereoselective method development and validation for determination of concentrations of amphetamine-type stimulants and metabolites in human urine using a simultaneous extraction-chiral derivatization approach. J Chromatogr B Analyt Technol Biomed Life Sci. 2011;879(1):8-16.
Wan Raihana, W. A., Gan, S. H., & Tan, S. C. (2011). Stereoselective method development and validation for determination of concentrations of amphetamine-type stimulants and metabolites in human urine using a simultaneous extraction-chiral derivatization approach. Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences, 879(1), 8-16. https://doi.org/10.1016/j.jchromb.2010.10.037
Wan Raihana WA, Gan SH, Tan SC. Stereoselective Method Development and Validation for Determination of Concentrations of Amphetamine-type Stimulants and Metabolites in Human Urine Using a Simultaneous Extraction-chiral Derivatization Approach. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Jan 1;879(1):8-16. PubMed PMID: 21147046.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereoselective method development and validation for determination of concentrations of amphetamine-type stimulants and metabolites in human urine using a simultaneous extraction-chiral derivatization approach. AU - Wan Raihana,W A, AU - Gan,S H, AU - Tan,S C, Y1 - 2010/11/24/ PY - 2010/08/25/received PY - 2010/10/27/revised PY - 2010/10/28/accepted PY - 2010/12/15/entrez PY - 2010/12/15/pubmed PY - 2011/4/13/medline SP - 8 EP - 16 JF - Journal of chromatography. B, Analytical technologies in the biomedical and life sciences JO - J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. VL - 879 IS - 1 N2 - Amphetamine-type stimulants (ATS) are a group of chiral amine drugs which are commonly abused for their sympathomimetic and stimulant properties. ATS are extensively metabolised by hepatic cytochrome P450 enzymes. As metabolism of ATS has been shown to be highly stereospecific, stereoselective analytical methods are essential for the quantitative determination of ATS concentrations for both in vivo and in vitro studies of ATS metabolism. This paper describes a new stereoselective method for the simultaneous determination of amphetamine (AM), methamphetamine (MA), 3,4-methylenedioxymethamphetamine (MDMA), 3,4-methylenedioxyamphetamine (MDA), 4-hydroxy-3-methoxymethamphetamine (HMMA), 4-hydroxy-3-methoxyamphetamine (HMA), 3,4-hydroxymethamphetamine (HHMA) and 3,4-hydroxyamphetamine (HHA) in human urine samples validated according to the United States Food and Drug Administration guidelines. In this method, analytes are simultaneously extracted and derivatized with R-(-)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride (R-MTPCl) as the chiral derivatization reagent. Following this, the analytes were subjected to a second derivatization with N-methyl-N-trimethylsilyltrifluoroacetamide (MSTFA) which targets the hydroxyl groups present in HMMA, HMA, HHMA and HHA. The derivatized analytes were separated and quantified using gas chromatography-mass spectrometry (GC-MS). The method was evaluated according to the established guidelines for specificity, linearity, precision, accuracy, recovery and stability using a five-day protocol. Intra-day precision ranged from 0.89 to 11.23% RSD whereas inter-day precision was between 1.03 and 12.95% RSD. Accuracy values for the analytes ranged from -5.29% to 13.75%. Limits of quantitation were 10 μg/L for AM, MA, MDMA, HMA and HMMA and 2μg/L for MDA, HMA and HHA. Recoveries and stability values were also within accepted values. The method was applied to authentic ATS-positive samples. SN - 1873-376X UR - https://www.unboundmedicine.com/medline/citation/21147046/Stereoselective_method_development_and_validation_for_determination_of_concentrations_of_amphetamine_type_stimulants_and_metabolites_in_human_urine_using_a_simultaneous_extraction_chiral_derivatization_approach_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S1570-0232(10)00684-7 DB - PRIME DP - Unbound Medicine ER -