Rapid enantiomeric separation and simultaneous determination of phenethylamines by ultra high performance liquid chromatography with fluorescence and mass spectrometric detection: application to the analysis of illicit drugs distributed in the Japanese market and biological samples
A rapid enantiomeric separation and simultaneous determination method based on ultra high performance liquid chromatography (UHPLC) was developed for phenethylamine‐type abused drugs using (R)‐(−)‐4‐(N,N‐dimethylaminosulfonyl)‐7‐(3‐isothiocyanatopyrrolidin‐1‐yl)‐2,1,3‐benzoxadiazole ((R)‐(−)‐DBD‐Py‐...
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| Veröffentlicht in: | Drug testing and analysis 2012-12, Vol.4 (12), p.1001-1008 |
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| creator | Inagaki, Shinsuke Hirashima, Haruo Taniguchi, Sayuri Higashi, Tatsuya Min, Jun Zhe Kikura-Hanajiri, Ruri Goda, Yukihiro Toyo'oka, Toshimasa |
| description | A rapid enantiomeric separation and simultaneous determination method based on ultra high performance liquid chromatography (UHPLC) was developed for phenethylamine‐type abused drugs using (R)‐(−)‐4‐(N,N‐dimethylaminosulfonyl)‐7‐(3‐isothiocyanatopyrrolidin‐1‐yl)‐2,1,3‐benzoxadiazole ((R)‐(−)‐DBD‐Py‐NCS) as the chiral fluorescent derivatization reagent. The derivatives were rapidly enantiomerically separated by reversed‐phase UHPLC using a column of 2.3‐µm octadecylsilica (ODS) particles by isocratic elution with water–methanol or water–acetonitrile systems as the mobile phase. The proposed method was applied to the analysis of products containing illicit drugs distributed in the Japanese market. Among the products, 1‐(3,4‐methylenedioxyphenyl)butan‐2‐amine (BDB) and 1‐(2‐methoxy4,5‐methylenedioxyphenyl)propan‐2‐amine (MMDA‐2) were detected in racemic form. Furthermore, the method was successfully applied to the analysis of hair specimens from rats that were continuously dosed with diphenyl(pyrrolidin‐2‐yl)methanol (D2PM). Using UHPLC‐fluorescence (FL) detection, (R)‐ and (S)‐D2PM from hair specimens were enantiomerically separated and detected with high sensitivity. The detection limits of (R)‐ and (S)‐D2PM were 0.12 and 0.21 ng/mg hair, respectively (signal‐to‐noise ratio (S/N) = 3). Copyright © 2012 John Wiley & Sons, Ltd.
A rapid enantiomeric separation and simultaneous determination method based on ultra high‐performance liquid chromatography (UHPLC) was developed for phenethylamine‐type abused drugs using (R)‐(‐)‐DBD‐Py‐NCS as the chiral derivatization reagent. The developed method was successfully applied to the analysis of hair specimens from rats that were dosed with diphenyl(pyrrolidin‐2‐yl)methanol (D2PM). (R)‐ and (S)‐D2PM from rat hair specimens were enantiomerically separated and detected high sensitivity using UHPLC‐fluorescence detection. |
| doi_str_mv | 10.1002/dta.1327 |
| format | Article |
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A rapid enantiomeric separation and simultaneous determination method based on ultra high‐performance liquid chromatography (UHPLC) was developed for phenethylamine‐type abused drugs using (R)‐(‐)‐DBD‐Py‐NCS as the chiral derivatization reagent. The developed method was successfully applied to the analysis of hair specimens from rats that were dosed with diphenyl(pyrrolidin‐2‐yl)methanol (D2PM). (R)‐ and (S)‐D2PM from rat hair specimens were enantiomerically separated and detected high sensitivity using UHPLC‐fluorescence detection.</description><identifier>ISSN: 1942-7603</identifier><identifier>EISSN: 1942-7611</identifier><identifier>DOI: 10.1002/dta.1327</identifier><identifier>PMID: 22407807</identifier><language>eng</language><publisher>England: Blackwell Publishing Ltd</publisher><subject>(R)-(−)-DBD-Py-NCS ; Acetonitriles - chemistry ; Animals ; Calibration ; chiral derivatization method ; Chromatography, High Pressure Liquid - standards ; Chromatography, Reverse-Phase ; diphenyl(pyrrolidin-2-yl)methanol (D2PM) ; Hair - chemistry ; Isothiocyanates - chemistry ; Japan ; Limit of Detection ; Male ; Methanol - chemistry ; Oxadiazoles - chemistry ; phenethylamines ; Phenethylamines - analysis ; Psychotropic Drugs - analysis ; Rats ; Reference Standards ; Signal-To-Noise Ratio ; Silicon Dioxide - chemistry ; Solvents - chemistry ; Spectrometry, Fluorescence - standards ; Spectrometry, Mass, Electrospray Ionization - standards ; Street Drugs - analysis ; Substance Abuse Detection - methods ; Substance Abuse Detection - standards ; ultra high performance liquid chromatography (UHPLC) ; Water - chemistry</subject><ispartof>Drug testing and analysis, 2012-12, Vol.4 (12), p.1001-1008</ispartof><rights>Copyright © 2012 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3877-660127bcb11446e27985350e9336cd5103205266400a53b59be57c7fd09443603</citedby><cites>FETCH-LOGICAL-c3877-660127bcb11446e27985350e9336cd5103205266400a53b59be57c7fd09443603</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fdta.1327$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fdta.1327$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22407807$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Inagaki, Shinsuke</creatorcontrib><creatorcontrib>Hirashima, Haruo</creatorcontrib><creatorcontrib>Taniguchi, Sayuri</creatorcontrib><creatorcontrib>Higashi, Tatsuya</creatorcontrib><creatorcontrib>Min, Jun Zhe</creatorcontrib><creatorcontrib>Kikura-Hanajiri, Ruri</creatorcontrib><creatorcontrib>Goda, Yukihiro</creatorcontrib><creatorcontrib>Toyo'oka, Toshimasa</creatorcontrib><title>Rapid enantiomeric separation and simultaneous determination of phenethylamines by ultra high performance liquid chromatography with fluorescence and mass spectrometric detection: application to the analysis of illicit drugs distributed in the Japanese market and biological samples</title><title>Drug testing and analysis</title><addtitle>Drug Test. Analysis</addtitle><description>A rapid enantiomeric separation and simultaneous determination method based on ultra high performance liquid chromatography (UHPLC) was developed for phenethylamine‐type abused drugs using (R)‐(−)‐4‐(N,N‐dimethylaminosulfonyl)‐7‐(3‐isothiocyanatopyrrolidin‐1‐yl)‐2,1,3‐benzoxadiazole ((R)‐(−)‐DBD‐Py‐NCS) as the chiral fluorescent derivatization reagent. The derivatives were rapidly enantiomerically separated by reversed‐phase UHPLC using a column of 2.3‐µm octadecylsilica (ODS) particles by isocratic elution with water–methanol or water–acetonitrile systems as the mobile phase. The proposed method was applied to the analysis of products containing illicit drugs distributed in the Japanese market. Among the products, 1‐(3,4‐methylenedioxyphenyl)butan‐2‐amine (BDB) and 1‐(2‐methoxy4,5‐methylenedioxyphenyl)propan‐2‐amine (MMDA‐2) were detected in racemic form. Furthermore, the method was successfully applied to the analysis of hair specimens from rats that were continuously dosed with diphenyl(pyrrolidin‐2‐yl)methanol (D2PM). Using UHPLC‐fluorescence (FL) detection, (R)‐ and (S)‐D2PM from hair specimens were enantiomerically separated and detected with high sensitivity. The detection limits of (R)‐ and (S)‐D2PM were 0.12 and 0.21 ng/mg hair, respectively (signal‐to‐noise ratio (S/N) = 3). Copyright © 2012 John Wiley & Sons, Ltd.
A rapid enantiomeric separation and simultaneous determination method based on ultra high‐performance liquid chromatography (UHPLC) was developed for phenethylamine‐type abused drugs using (R)‐(‐)‐DBD‐Py‐NCS as the chiral derivatization reagent. The developed method was successfully applied to the analysis of hair specimens from rats that were dosed with diphenyl(pyrrolidin‐2‐yl)methanol (D2PM). (R)‐ and (S)‐D2PM from rat hair specimens were enantiomerically separated and detected high sensitivity using UHPLC‐fluorescence detection.</description><subject>(R)-(−)-DBD-Py-NCS</subject><subject>Acetonitriles - chemistry</subject><subject>Animals</subject><subject>Calibration</subject><subject>chiral derivatization method</subject><subject>Chromatography, High Pressure Liquid - standards</subject><subject>Chromatography, Reverse-Phase</subject><subject>diphenyl(pyrrolidin-2-yl)methanol (D2PM)</subject><subject>Hair - chemistry</subject><subject>Isothiocyanates - chemistry</subject><subject>Japan</subject><subject>Limit of Detection</subject><subject>Male</subject><subject>Methanol - chemistry</subject><subject>Oxadiazoles - chemistry</subject><subject>phenethylamines</subject><subject>Phenethylamines - analysis</subject><subject>Psychotropic Drugs - analysis</subject><subject>Rats</subject><subject>Reference Standards</subject><subject>Signal-To-Noise Ratio</subject><subject>Silicon Dioxide - chemistry</subject><subject>Solvents - chemistry</subject><subject>Spectrometry, Fluorescence - standards</subject><subject>Spectrometry, Mass, Electrospray Ionization - standards</subject><subject>Street Drugs - analysis</subject><subject>Substance Abuse Detection - methods</subject><subject>Substance Abuse Detection - standards</subject><subject>ultra high performance liquid chromatography (UHPLC)</subject><subject>Water - chemistry</subject><issn>1942-7603</issn><issn>1942-7611</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kk1v1DAQhgMC0VKQOHNAlrhw2eKPJG64VQVaoAKEijhajjO7cXFi13ZU8u-ZdJdFQuLkj3n8vjPjKYpnjB4zSvnrLutjJri8XxyypuQrWTP2YL-n4qB4nNI1pXXJRfWoOOC8pPKEysN7z7_pYDsCox6z9QNEa0iCoKPG40j02JFkh8llPYKfEukgQxzsuA37NQk9jJD72Wm8hUTamSAdNentpicB4trHQY8GiLM3E1qZPvpBZ7-JOvQzubW5J2s3-QjJwMItnoNOiaQAJiMMeclqcTaL6xuiQ3DWbFPInuR-eaTdnGxaUrIOozaTLk4bzNgmfN9OGTpixzv4ow5YTgK0iT8h3zm21ju_QVVHkh6Cg_SkeLjWLsHT3XpUfH__7ursYnX55fzD2enlyogTKVd1TRmXrWkZK8sauGxOKlFRaISoTVcxKjiteF2XlOpKtFXTQiWNXHe0KUuBn3NUvNrqhuhvJkhZDRZb4dy25QrVBeesbBpEX_6DXvspYukLJRqJkBR_BU30KUVYqxAtljorRtUyLwrnRS3zguiLneDUDtDtwT8DgsBqC9xaB_N_hdTbq9Od4I7HrsOvPY99VrUUslI_Pp-rr_wTvyhprYT4DYVN3vE</recordid><startdate>201212</startdate><enddate>201212</enddate><creator>Inagaki, Shinsuke</creator><creator>Hirashima, Haruo</creator><creator>Taniguchi, Sayuri</creator><creator>Higashi, Tatsuya</creator><creator>Min, Jun Zhe</creator><creator>Kikura-Hanajiri, Ruri</creator><creator>Goda, Yukihiro</creator><creator>Toyo'oka, Toshimasa</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>201212</creationdate><title>Rapid enantiomeric separation and simultaneous determination of phenethylamines by ultra high performance liquid chromatography with fluorescence and mass spectrometric detection: application to the analysis of illicit drugs distributed in the Japanese market and biological samples</title><author>Inagaki, Shinsuke ; Hirashima, Haruo ; Taniguchi, Sayuri ; Higashi, Tatsuya ; Min, Jun Zhe ; Kikura-Hanajiri, Ruri ; Goda, Yukihiro ; Toyo'oka, Toshimasa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3877-660127bcb11446e27985350e9336cd5103205266400a53b59be57c7fd09443603</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>(R)-(−)-DBD-Py-NCS</topic><topic>Acetonitriles - chemistry</topic><topic>Animals</topic><topic>Calibration</topic><topic>chiral derivatization method</topic><topic>Chromatography, High Pressure Liquid - standards</topic><topic>Chromatography, Reverse-Phase</topic><topic>diphenyl(pyrrolidin-2-yl)methanol (D2PM)</topic><topic>Hair - chemistry</topic><topic>Isothiocyanates - chemistry</topic><topic>Japan</topic><topic>Limit of Detection</topic><topic>Male</topic><topic>Methanol - chemistry</topic><topic>Oxadiazoles - chemistry</topic><topic>phenethylamines</topic><topic>Phenethylamines - analysis</topic><topic>Psychotropic Drugs - analysis</topic><topic>Rats</topic><topic>Reference Standards</topic><topic>Signal-To-Noise Ratio</topic><topic>Silicon Dioxide - chemistry</topic><topic>Solvents - chemistry</topic><topic>Spectrometry, Fluorescence - standards</topic><topic>Spectrometry, Mass, Electrospray Ionization - standards</topic><topic>Street Drugs - analysis</topic><topic>Substance Abuse Detection - methods</topic><topic>Substance Abuse Detection - standards</topic><topic>ultra high performance liquid chromatography (UHPLC)</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Inagaki, Shinsuke</creatorcontrib><creatorcontrib>Hirashima, Haruo</creatorcontrib><creatorcontrib>Taniguchi, Sayuri</creatorcontrib><creatorcontrib>Higashi, Tatsuya</creatorcontrib><creatorcontrib>Min, Jun Zhe</creatorcontrib><creatorcontrib>Kikura-Hanajiri, Ruri</creatorcontrib><creatorcontrib>Goda, Yukihiro</creatorcontrib><creatorcontrib>Toyo'oka, Toshimasa</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Drug testing and analysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Inagaki, Shinsuke</au><au>Hirashima, Haruo</au><au>Taniguchi, Sayuri</au><au>Higashi, Tatsuya</au><au>Min, Jun Zhe</au><au>Kikura-Hanajiri, Ruri</au><au>Goda, Yukihiro</au><au>Toyo'oka, Toshimasa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rapid enantiomeric separation and simultaneous determination of phenethylamines by ultra high performance liquid chromatography with fluorescence and mass spectrometric detection: application to the analysis of illicit drugs distributed in the Japanese market and biological samples</atitle><jtitle>Drug testing and analysis</jtitle><addtitle>Drug Test. Analysis</addtitle><date>2012-12</date><risdate>2012</risdate><volume>4</volume><issue>12</issue><spage>1001</spage><epage>1008</epage><pages>1001-1008</pages><issn>1942-7603</issn><eissn>1942-7611</eissn><abstract>A rapid enantiomeric separation and simultaneous determination method based on ultra high performance liquid chromatography (UHPLC) was developed for phenethylamine‐type abused drugs using (R)‐(−)‐4‐(N,N‐dimethylaminosulfonyl)‐7‐(3‐isothiocyanatopyrrolidin‐1‐yl)‐2,1,3‐benzoxadiazole ((R)‐(−)‐DBD‐Py‐NCS) as the chiral fluorescent derivatization reagent. The derivatives were rapidly enantiomerically separated by reversed‐phase UHPLC using a column of 2.3‐µm octadecylsilica (ODS) particles by isocratic elution with water–methanol or water–acetonitrile systems as the mobile phase. The proposed method was applied to the analysis of products containing illicit drugs distributed in the Japanese market. Among the products, 1‐(3,4‐methylenedioxyphenyl)butan‐2‐amine (BDB) and 1‐(2‐methoxy4,5‐methylenedioxyphenyl)propan‐2‐amine (MMDA‐2) were detected in racemic form. Furthermore, the method was successfully applied to the analysis of hair specimens from rats that were continuously dosed with diphenyl(pyrrolidin‐2‐yl)methanol (D2PM). Using UHPLC‐fluorescence (FL) detection, (R)‐ and (S)‐D2PM from hair specimens were enantiomerically separated and detected with high sensitivity. The detection limits of (R)‐ and (S)‐D2PM were 0.12 and 0.21 ng/mg hair, respectively (signal‐to‐noise ratio (S/N) = 3). Copyright © 2012 John Wiley & Sons, Ltd.
A rapid enantiomeric separation and simultaneous determination method based on ultra high‐performance liquid chromatography (UHPLC) was developed for phenethylamine‐type abused drugs using (R)‐(‐)‐DBD‐Py‐NCS as the chiral derivatization reagent. The developed method was successfully applied to the analysis of hair specimens from rats that were dosed with diphenyl(pyrrolidin‐2‐yl)methanol (D2PM). (R)‐ and (S)‐D2PM from rat hair specimens were enantiomerically separated and detected high sensitivity using UHPLC‐fluorescence detection.</abstract><cop>England</cop><pub>Blackwell Publishing Ltd</pub><pmid>22407807</pmid><doi>10.1002/dta.1327</doi><tpages>8</tpages></addata></record> |
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| subjects | (R)-(−)-DBD-Py-NCS Acetonitriles - chemistry Animals Calibration chiral derivatization method Chromatography, High Pressure Liquid - standards Chromatography, Reverse-Phase diphenyl(pyrrolidin-2-yl)methanol (D2PM) Hair - chemistry Isothiocyanates - chemistry Japan Limit of Detection Male Methanol - chemistry Oxadiazoles - chemistry phenethylamines Phenethylamines - analysis Psychotropic Drugs - analysis Rats Reference Standards Signal-To-Noise Ratio Silicon Dioxide - chemistry Solvents - chemistry Spectrometry, Fluorescence - standards Spectrometry, Mass, Electrospray Ionization - standards Street Drugs - analysis Substance Abuse Detection - methods Substance Abuse Detection - standards ultra high performance liquid chromatography (UHPLC) Water - chemistry |
| title | Rapid enantiomeric separation and simultaneous determination of phenethylamines by ultra high performance liquid chromatography with fluorescence and mass spectrometric detection: application to the analysis of illicit drugs distributed in the Japanese market and biological samples |
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