生物样品中镇静类药物检测的研究进展
Research Progress on Detection of Sedative Drugs in Biological Samples
摘 要
综述了近10年来生物样品中镇静类药物的检测方法（包括高效液相色谱法、气相色谱-质谱法、液相色谱-串联质谱法和液相色谱-高分辨质谱法等）和样品预处理方法（包括液液萃取法、固相萃取法、分散固相萃取法和柱切换法等）的研究进展，并对其前景作了简要展望（引用文献45篇）。
镇静类药物
检测
综述
biological sample
sedative drug
detection
review
Abstract
A review on research progress on detection methods (including HPLC, GC-MS, LC-MS/MS, LC-HRMS and so on) and sample pretreatment methods (including liquid liquid extraction, solid phase extraction, dispersed solid phase extraction, column switching and so on) used in the detection of sedative drugs in biological samples in the last 10 years was presented. A brief prospect was also given (45 ref. cited).
中图分类号 O65 DOI 10.11973/lhjy-hx202005022
所属栏目 专题报道(药物分析)
基金项目 宁波市“科技创新2025”重大专项（2018B10075）；浙江省自然科学基金项目（LY18B050001）；国家自然科学基金项目（21677128）
收稿日期 2019/7/23
修改稿日期
网络出版日期
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联系人作者金米聪(jmcjc@163.com)
备注陈晓红,硕士,主要从事理化检验工作
引用该论文: CHEN Xiaohong,LIN Meng,JIN Micong. Research Progress on Detection of Sedative Drugs in Biological Samples[J]. Physical Testing and Chemical Analysis part B:Chemical Analysis, 2020, 56(5): 612～620
陈晓红,林梦,金米聪. 生物样品中镇静类药物检测的研究进展[J]. 理化检验－化学分册, 2020, 56(5): 612～620
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参考文献
【1】WEYMANN D, GLADSTONE E J, SMOLINA K, et al. Long-term sedative use among community-dwelling adults:A population-based analysis[J]. CMAJ Open, 2017,5(1):52-60.
【2】KRIIKKU P, HURME H, WILHELM L, et al. Sedative-hypnotics are widely abused by drivers apprehended for driving under the influence of drugs[J]. Therapeutic Drug Monitoring, 2015,37(3):339-346.
【3】BIRKLER R I D, TELVING R, INGEMANN-HANSEN O, et al. Screening analysis for medicinal drugs and drugs of abuse in whole blood using ultra-performance liquid chromatography time-of-flight mass spectrometry (UPLC-TOF-MS) Toxicological findings in cases of alleged sexual assault[J]. Forensic Science International, 2012,222(1/2/3):154-161.
【4】HANSEN R N, BOUDREAU D M, EBEL B E, et al. Sedative hypnotic medication use and the risk of motor vehicle crash[J]. American Journal of Public Health, 2015,105(8):64-69.
【5】孙树森,赵志刚.临床药师与药物中毒:镇静催眠和抗精神病药物[J].药品评价, 2016,13(2):8-16.
【6】韩菊平,刘晋.132例镇静催眠药物急性中毒分析[J].江汉大学学报(自然科学版), 2013,41(3):89-91.
【7】梁湘辉,戴智勇,刘文恩.反向高效液相色谱测定法同时测定人血浆中5种镇静催眠药浓度[J].中南大学学报(医学版), 2009,34(7):689-693.
【8】范盛先,黄玲利,袁宗辉,等.猪肾脏中氯丙嗪和异丙嗪残留检测方法的建立[J].中国兽医学报, 2005,25(4):412-413.
【9】李亮亮.固相萃取-HPLC法同时测定人血浆中4种苯二氮卓类药物[J].海峡药学, 2017,29(11):34-37.
【10】PEBDANI A A, KHODADOUST S, TALEBIANPOOR M S, et al. Preconcentration and determination of chlordiazepoxide and diazepam drugs using dispersive nanomaterial-ultrasound assisted microextraction method followed by high performance liquid chromatography[J]. Journal of Chromatography B, 2016,1008:146-155.
【11】ÁLVAREZ-FREIRE I, BRUNETTI P, CABARCOS-FERNÁNDEZ P, et al. Determination of benzodiazepines in pericardial fluid by gas chromatography-mass spectrometry[J]. Journal of Pharmaceutical and Biomedical Analysis, 2018,159:45-52.
【12】常青,马虹英,王方杰,等.脉冲不分流进样气相色谱-质谱法分析血浆中的10种镇静催眠药[J].色谱, 2011,29(11):1082-1086.
【13】PAPOUTSIS I I, ATHANASELIS S A, NIKOLAOU P D, et al. Development and validation of an EI-GC-MS method for the determination of benzodiazepine drugs and their metabolites in blood:Applications in clinical and forensic toxicology[J]. Journal of Pharmaceutical and Biomedical Analysis, 2010,52(4):609-614.
【14】吴惠勤,金永春,蔡明招,等.气相色谱-质谱法同时检测10种常见精神类药物[J].分析化学, 2007,35(4):500-504.
【15】CORDERO R, PATERSON S. Simultaneous quantification of opiates, amphetamines, cocaine and metabolites and diazepam and metabolite in a single hair sample using GC-MS[J]. Journal of Chromatography B, 2007,850(1/2):423-431.
【16】孙红雷,李文海.血中安眠药物的固相萃取GC/MS分析方法研究[J].分析测试技术与仪器, 2008,14(4):209-213.
【17】AO J J, YUAN T, MA Y N, et al. Identification, characteristics and human exposure assessments of triclosan, bisphenol-A, and four commonly used organic UV filters in indoor dust collected from Shanghai, China[J]. Chemosphere, 2017,184:575-583.
【18】李存,皇甫伟国,杨挺,等.液相色谱串联质谱法快速测定猪尿中10种镇静剂类药物残留量[J].分析化学, 2010,38(7):1015-1018.
【19】SMINK B E, BRANDSMA J E, DIJKHUIZEN A, et al. Quantitative analysis of 33 benzodiazepines, metabolites and benzodiazepine-like substances in whole blood by liquid chromatography-(tandem) mass spectrometry[J]. Journal of Chromatography B, 2004,811(1):13-20.
【20】WANG Z, SUN W, LIN Z F, et al. A UHPLC-MS/MS method coupled with liquid-liquid extraction for the quantitation of phenacetin, omeprazole, metoprolol, midazolam and their metabolites in rat plasma and its application to the study of four CYP450 activities[J]. Journal of Pharmaceutical and Biomedical Analysis, 2019,163:204-210.
【21】SIM J, KIM E, YANG W, et al. An LC-MS/MS method for the simultaneous determination of 15 antipsychotics and two metabolites in hair and its application to rat hair[J]. Forensic Science International, 2017,274:91-98.
【22】RUST K Y, BAUMGARTNER M R, MEGGIOLARO N, et al. Detection and validated quantification of 21 benzodiazepines and 3"z-drugs" in human hair by LC-MS/MS[J]. Forensic Science International, 2012,215(1/2/3):64-72.
【23】CHZE M, VILLAIN M, PÉPIN G. Determination of bromazepam,clonazepam and metabolites after a single intake in urine and hair by LC-MS/MS[J]. Forensic Science International, 2004,145(2/3):123-130.
【24】GHASSABIAN S, MOOSAVI S M, VALERO Y G, et al. High-throughput assay for simultaneous quantification of the plasma concentrations of morphine, fentanyl, midazolam and their major metabolites using automated SPE coupled to LC-MS/MS[J]. Journal of Chromatography B, 2012,903:126-133.
【25】IRVING R C, DICKSON S J. The detection of sedatives in hair and nail samples using tandem LC-MS-MS[J]. Forensic Science International, 2007,166(1):58-67.
【26】MONTESANO C, JOHANSEN S S, NIELSEN M K K. Validation of a method for the targeted analysis of 96 drugs in hair by UPLC-MS/MS[J]. Journal of Pharmaceutical and Biomedical Analysis, 2014,88:295-306.
【27】SONG A Y. Determination of 13 organic toxicants in human blood by liquid-liquid extraction coupling high-performance liquid chromatography tandem mass spectrometry[J]. Analytical Sciences, 2016,32(6):645-652.
【28】KINTZ P, VILLAIN M, DUMESTRE-TOULET V, et al. Drug-facilitated sexual assault and analytical toxicology:The role of LC-MS/MS:A case involving zolpidem[J]. Journal of Clinical Forensic Medicine, 2005,12(1):36-41.
【29】RAMÍREZ FERNÁNDEZ MDEL M, WILLE S M, DI FAZIO V, et al. Detection of benzodiazepines and z-drugs in hair using an UHPLC-MS/MS validated method:Application to workplace drug testing[J]. Therapeutic Drug Monitoring, 2015,37(5):600-608.
【30】KHELFI A, AZZOUZ M, ABTROUN R, et al. Determination of chlorpromazine, haloperidol, levomepromazine, olanzapine, risperidone, and sulpiride in human plasma by liquid chromatography/tandem mass spectrometry (LC-MS/MS)[J]. International Journal of Analytical Chemistry, 2018,2018:1-13.
【31】WANG R, WANG X, LIANG C, et al. Direct determination of diazepam and its glucuronide metabolites in human whole blood by μElution solid-phase extraction and liquid chromatography-tandem mass spectrometry[J]. Forensic Science International, 2013,233(1/2/3):304-311.
【32】DOMINGUES D S, DE SOUZA I D, QUEIROZ M E C. Analysis of drugs in plasma samples from schizophrenic patients by column-switching liquid chromatography-tandem mass spectrometry with organic-inorganic hybrid cyanopropyl monolithic column[J]. Journal of Chromatography B, 2015,993/994:26-35.
【33】LEE X P, SHOUJI Y, KUMAZAWA T, et al. Rapid and highly sensitive analysis of benzodiazepines and tandospirone in human plasma by automated on-line column-switching UFLC-MS/MS[J]. Legal Medicine, 2017,24:36-55.
【34】夏曦,李晓薇,丁双阳,等.液相色谱-高分辨质谱在兽药残留分析中的应用进展[J].质谱学报, 2011,32(6):333-340.
【35】ODOARDI S, VALENTINI V, DE GIOVANNI N, et al. High-throughput screening for drugs of abuse and pharmaceutical drugs in hair by liquid-chromatography-high resolution mass spectrometry (LC-HRMS)[J]. Microchemical Journal, 2017,133:302-310.
【36】PETTERSSON BERGSTRAND M, BECK O, HELANDER A. Urine analysis of 28 designer benzodiazepines by liquid chromatography-high-resolution mass spectrometry[J]. Clinical Mass Spectrometry, 2018,10:25-32.
【37】MAGALHÃES E J, NASCENTES C C, AUGUSTI R, et al. Fast determination of benzodiazepines in human urine via liquid-liquid extraction with low temperature partitioning and LC-HRMS[J]. American Journal of Analytical Chemistry, 2012,3(2):118-124.
【38】VOGLIARDI S, FAVRETTO D, TUCCI M, et al. Simultaneous LC-HRMS determination of 28 benzodiazepines and metabolites in hair[J]. Analytical and Bioanalytical Chemistry, 2011,400(1):51-67.
【39】KALOGRIA E, PISTOS C, PANDERI I. Hydrophilic interaction liquid chromatography/positive ion electrospray ionization mass spectrometry method for the quantification of alprazolam and α-hydroxy-alprazolam in human plasma[J]. Journal of Chromatography B, 2013,942:158-164.
【40】PLÖSSL F, GIERA M, BRACHER F. Multiresidue analytical method using dispersive solid-phase extraction and gas chromatography/ion trap mass spectrometry to determine pharmaceuticals in whole blood[J]. Journal of Chromatography A, 2006,1135(1):19-26.
【41】CUI X Z, NI C F, LIANG C, et al. Screening and quantitation of forty-six drugs of abuse and toxic compounds in human whole blood by capillary electrophoresis:Application to forensic cases[J]. Microchemical Journal, 2019,144:403-410.
【42】YAO W X, FAN Z F, ZHANG S L. Poly(methacrylic acid-ethylene glycol dimethacrylate-N-vinylcarbazole) monolithic column for the enrichment of trace benzodiazepines from urine and beer samples[J]. Journal of Separation Science, 2017,40(6):1369-1376.
【43】AHRENS B, BLANKENHORN D, SPANGENBERG B. Advanced fibre optical scanning in thin-layer chromatography for drug identification[J]. Journal of Chromatography B, 2002,772(1):11-18.
【44】RIAHI S, BAGHERZADEH K, DAVARKHAH N, et al. Spectrophotometric and chemometric studies on the simultaneous determination of two benzodiazepines in human plasma[J]. Materials Science and Engineering:C, 2011,31(5):992-996.
【2】KRIIKKU P, HURME H, WILHELM L, et al. Sedative-hypnotics are widely abused by drivers apprehended for driving under the influence of drugs[J]. Therapeutic Drug Monitoring, 2015,37(3):339-346.
【3】BIRKLER R I D, TELVING R, INGEMANN-HANSEN O, et al. Screening analysis for medicinal drugs and drugs of abuse in whole blood using ultra-performance liquid chromatography time-of-flight mass spectrometry (UPLC-TOF-MS) Toxicological findings in cases of alleged sexual assault[J]. Forensic Science International, 2012,222(1/2/3):154-161.
【4】HANSEN R N, BOUDREAU D M, EBEL B E, et al. Sedative hypnotic medication use and the risk of motor vehicle crash[J]. American Journal of Public Health, 2015,105(8):64-69.
【5】孙树森,赵志刚.临床药师与药物中毒:镇静催眠和抗精神病药物[J].药品评价, 2016,13(2):8-16.
【6】韩菊平,刘晋.132例镇静催眠药物急性中毒分析[J].江汉大学学报(自然科学版), 2013,41(3):89-91.
【7】梁湘辉,戴智勇,刘文恩.反向高效液相色谱测定法同时测定人血浆中5种镇静催眠药浓度[J].中南大学学报(医学版), 2009,34(7):689-693.
【8】范盛先,黄玲利,袁宗辉,等.猪肾脏中氯丙嗪和异丙嗪残留检测方法的建立[J].中国兽医学报, 2005,25(4):412-413.
【9】李亮亮.固相萃取-HPLC法同时测定人血浆中4种苯二氮卓类药物[J].海峡药学, 2017,29(11):34-37.
【10】PEBDANI A A, KHODADOUST S, TALEBIANPOOR M S, et al. Preconcentration and determination of chlordiazepoxide and diazepam drugs using dispersive nanomaterial-ultrasound assisted microextraction method followed by high performance liquid chromatography[J]. Journal of Chromatography B, 2016,1008:146-155.
【11】ÁLVAREZ-FREIRE I, BRUNETTI P, CABARCOS-FERNÁNDEZ P, et al. Determination of benzodiazepines in pericardial fluid by gas chromatography-mass spectrometry[J]. Journal of Pharmaceutical and Biomedical Analysis, 2018,159:45-52.
【12】常青,马虹英,王方杰,等.脉冲不分流进样气相色谱-质谱法分析血浆中的10种镇静催眠药[J].色谱, 2011,29(11):1082-1086.
【13】PAPOUTSIS I I, ATHANASELIS S A, NIKOLAOU P D, et al. Development and validation of an EI-GC-MS method for the determination of benzodiazepine drugs and their metabolites in blood:Applications in clinical and forensic toxicology[J]. Journal of Pharmaceutical and Biomedical Analysis, 2010,52(4):609-614.
【14】吴惠勤,金永春,蔡明招,等.气相色谱-质谱法同时检测10种常见精神类药物[J].分析化学, 2007,35(4):500-504.
【15】CORDERO R, PATERSON S. Simultaneous quantification of opiates, amphetamines, cocaine and metabolites and diazepam and metabolite in a single hair sample using GC-MS[J]. Journal of Chromatography B, 2007,850(1/2):423-431.
【16】孙红雷,李文海.血中安眠药物的固相萃取GC/MS分析方法研究[J].分析测试技术与仪器, 2008,14(4):209-213.
【17】AO J J, YUAN T, MA Y N, et al. Identification, characteristics and human exposure assessments of triclosan, bisphenol-A, and four commonly used organic UV filters in indoor dust collected from Shanghai, China[J]. Chemosphere, 2017,184:575-583.
【18】李存,皇甫伟国,杨挺,等.液相色谱串联质谱法快速测定猪尿中10种镇静剂类药物残留量[J].分析化学, 2010,38(7):1015-1018.
【19】SMINK B E, BRANDSMA J E, DIJKHUIZEN A, et al. Quantitative analysis of 33 benzodiazepines, metabolites and benzodiazepine-like substances in whole blood by liquid chromatography-(tandem) mass spectrometry[J]. Journal of Chromatography B, 2004,811(1):13-20.
【20】WANG Z, SUN W, LIN Z F, et al. A UHPLC-MS/MS method coupled with liquid-liquid extraction for the quantitation of phenacetin, omeprazole, metoprolol, midazolam and their metabolites in rat plasma and its application to the study of four CYP450 activities[J]. Journal of Pharmaceutical and Biomedical Analysis, 2019,163:204-210.
【21】SIM J, KIM E, YANG W, et al. An LC-MS/MS method for the simultaneous determination of 15 antipsychotics and two metabolites in hair and its application to rat hair[J]. Forensic Science International, 2017,274:91-98.
【22】RUST K Y, BAUMGARTNER M R, MEGGIOLARO N, et al. Detection and validated quantification of 21 benzodiazepines and 3"z-drugs" in human hair by LC-MS/MS[J]. Forensic Science International, 2012,215(1/2/3):64-72.
【23】CHZE M, VILLAIN M, PÉPIN G. Determination of bromazepam,clonazepam and metabolites after a single intake in urine and hair by LC-MS/MS[J]. Forensic Science International, 2004,145(2/3):123-130.
【24】GHASSABIAN S, MOOSAVI S M, VALERO Y G, et al. High-throughput assay for simultaneous quantification of the plasma concentrations of morphine, fentanyl, midazolam and their major metabolites using automated SPE coupled to LC-MS/MS[J]. Journal of Chromatography B, 2012,903:126-133.
【25】IRVING R C, DICKSON S J. The detection of sedatives in hair and nail samples using tandem LC-MS-MS[J]. Forensic Science International, 2007,166(1):58-67.
【26】MONTESANO C, JOHANSEN S S, NIELSEN M K K. Validation of a method for the targeted analysis of 96 drugs in hair by UPLC-MS/MS[J]. Journal of Pharmaceutical and Biomedical Analysis, 2014,88:295-306.
【27】SONG A Y. Determination of 13 organic toxicants in human blood by liquid-liquid extraction coupling high-performance liquid chromatography tandem mass spectrometry[J]. Analytical Sciences, 2016,32(6):645-652.
【28】KINTZ P, VILLAIN M, DUMESTRE-TOULET V, et al. Drug-facilitated sexual assault and analytical toxicology:The role of LC-MS/MS:A case involving zolpidem[J]. Journal of Clinical Forensic Medicine, 2005,12(1):36-41.
【29】RAMÍREZ FERNÁNDEZ MDEL M, WILLE S M, DI FAZIO V, et al. Detection of benzodiazepines and z-drugs in hair using an UHPLC-MS/MS validated method:Application to workplace drug testing[J]. Therapeutic Drug Monitoring, 2015,37(5):600-608.
【30】KHELFI A, AZZOUZ M, ABTROUN R, et al. Determination of chlorpromazine, haloperidol, levomepromazine, olanzapine, risperidone, and sulpiride in human plasma by liquid chromatography/tandem mass spectrometry (LC-MS/MS)[J]. International Journal of Analytical Chemistry, 2018,2018:1-13.
【31】WANG R, WANG X, LIANG C, et al. Direct determination of diazepam and its glucuronide metabolites in human whole blood by μElution solid-phase extraction and liquid chromatography-tandem mass spectrometry[J]. Forensic Science International, 2013,233(1/2/3):304-311.
【32】DOMINGUES D S, DE SOUZA I D, QUEIROZ M E C. Analysis of drugs in plasma samples from schizophrenic patients by column-switching liquid chromatography-tandem mass spectrometry with organic-inorganic hybrid cyanopropyl monolithic column[J]. Journal of Chromatography B, 2015,993/994:26-35.
【33】LEE X P, SHOUJI Y, KUMAZAWA T, et al. Rapid and highly sensitive analysis of benzodiazepines and tandospirone in human plasma by automated on-line column-switching UFLC-MS/MS[J]. Legal Medicine, 2017,24:36-55.
【34】夏曦,李晓薇,丁双阳,等.液相色谱-高分辨质谱在兽药残留分析中的应用进展[J].质谱学报, 2011,32(6):333-340.
【35】ODOARDI S, VALENTINI V, DE GIOVANNI N, et al. High-throughput screening for drugs of abuse and pharmaceutical drugs in hair by liquid-chromatography-high resolution mass spectrometry (LC-HRMS)[J]. Microchemical Journal, 2017,133:302-310.
【36】PETTERSSON BERGSTRAND M, BECK O, HELANDER A. Urine analysis of 28 designer benzodiazepines by liquid chromatography-high-resolution mass spectrometry[J]. Clinical Mass Spectrometry, 2018,10:25-32.
【37】MAGALHÃES E J, NASCENTES C C, AUGUSTI R, et al. Fast determination of benzodiazepines in human urine via liquid-liquid extraction with low temperature partitioning and LC-HRMS[J]. American Journal of Analytical Chemistry, 2012,3(2):118-124.
【38】VOGLIARDI S, FAVRETTO D, TUCCI M, et al. Simultaneous LC-HRMS determination of 28 benzodiazepines and metabolites in hair[J]. Analytical and Bioanalytical Chemistry, 2011,400(1):51-67.
【39】KALOGRIA E, PISTOS C, PANDERI I. Hydrophilic interaction liquid chromatography/positive ion electrospray ionization mass spectrometry method for the quantification of alprazolam and α-hydroxy-alprazolam in human plasma[J]. Journal of Chromatography B, 2013,942:158-164.
【40】PLÖSSL F, GIERA M, BRACHER F. Multiresidue analytical method using dispersive solid-phase extraction and gas chromatography/ion trap mass spectrometry to determine pharmaceuticals in whole blood[J]. Journal of Chromatography A, 2006,1135(1):19-26.
【41】CUI X Z, NI C F, LIANG C, et al. Screening and quantitation of forty-six drugs of abuse and toxic compounds in human whole blood by capillary electrophoresis:Application to forensic cases[J]. Microchemical Journal, 2019,144:403-410.
【42】YAO W X, FAN Z F, ZHANG S L. Poly(methacrylic acid-ethylene glycol dimethacrylate-N-vinylcarbazole) monolithic column for the enrichment of trace benzodiazepines from urine and beer samples[J]. Journal of Separation Science, 2017,40(6):1369-1376.
【43】AHRENS B, BLANKENHORN D, SPANGENBERG B. Advanced fibre optical scanning in thin-layer chromatography for drug identification[J]. Journal of Chromatography B, 2002,772(1):11-18.
【44】RIAHI S, BAGHERZADEH K, DAVARKHAH N, et al. Spectrophotometric and chemometric studies on the simultaneous determination of two benzodiazepines in human plasma[J]. Materials Science and Engineering:C, 2011,31(5):992-996.
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