Characterization of in vitro phase I metabolites of methamnetamine in human liver microsomes by liquid chromatography-quadrupole time-of-flight mass spectrometry
N -Methyl-1-(naphthalen-2-yl)propan-2-amine (methamnetamine, PAL-1046) is an amphetamine-based new psychoactive substance (NPS). Methamnetamine has been reported to cause excessive release of serotonin, and it is classified as an empathogen or entactogen. It is not regulated as a controlled substanc...
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| Veröffentlicht in: | International journal of legal medicine 2021-07, Vol.135 (4), p.1471-1476 |
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| container_title | International journal of legal medicine |
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| creator | Hong, Young-ki Kim, Young-Hoon Lee, Jin-Moo Yoo, Hye Hyun Choi, Sun-Ok Kang, Mi Sun |
| description | N
-Methyl-1-(naphthalen-2-yl)propan-2-amine (methamnetamine, PAL-1046) is an amphetamine-based new psychoactive substance (NPS). Methamnetamine has been reported to cause excessive release of serotonin, and it is classified as an empathogen or entactogen. It is not regulated as a controlled substance in most countries, and there are no studies on its metabolism. In this study, in vitro phase I metabolism of methamnetamine in human liver microsomes (HLM) and flavin-containing monooxygenase (FMO) was investigated by liquid chromatography-quadrupole time-of-flight mass spectrometry (LC-Q-TOF/MS). Eight metabolites of methamnetamine were identified and were structurally characterized achieved by a combination of accurate mass analysis and tandem mass spectrometry. The identified metabolic processes include
N
-demethylation,
N
-hydroxylation, aromatic hydroxylation, and a combination of these processes.
N
-Hydroxylated metabolites were confirmed based on expressed FMOs. The major metabolite was formed from methamnetamine via hydroxylation of the naphthalene ring after the in vitro phase I process. These results could help detect methamnetamine ingestion by NPS abusers. |
| doi_str_mv | 10.1007/s00414-021-02594-z |
| format | Article |
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-Methyl-1-(naphthalen-2-yl)propan-2-amine (methamnetamine, PAL-1046) is an amphetamine-based new psychoactive substance (NPS). Methamnetamine has been reported to cause excessive release of serotonin, and it is classified as an empathogen or entactogen. It is not regulated as a controlled substance in most countries, and there are no studies on its metabolism. In this study, in vitro phase I metabolism of methamnetamine in human liver microsomes (HLM) and flavin-containing monooxygenase (FMO) was investigated by liquid chromatography-quadrupole time-of-flight mass spectrometry (LC-Q-TOF/MS). Eight metabolites of methamnetamine were identified and were structurally characterized achieved by a combination of accurate mass analysis and tandem mass spectrometry. The identified metabolic processes include
N
-demethylation,
N
-hydroxylation, aromatic hydroxylation, and a combination of these processes.
N
-Hydroxylated metabolites were confirmed based on expressed FMOs. The major metabolite was formed from methamnetamine via hydroxylation of the naphthalene ring after the in vitro phase I process. These results could help detect methamnetamine ingestion by NPS abusers.</description><identifier>ISSN: 0937-9827</identifier><identifier>EISSN: 1437-1596</identifier><identifier>DOI: 10.1007/s00414-021-02594-z</identifier><identifier>PMID: 33928430</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Amphetamines ; Chromatography ; Forensic Medicine ; Hydroxylation ; Ingestion ; Ions ; Liquid chromatography ; Liver ; Mass spectrometry ; Medical Law ; Medicine ; Medicine & Public Health ; Metabolism ; Metabolites ; Naphthalene ; Quadrupoles ; Scientific imaging ; Serotonin ; Short Communication ; Spectroscopy</subject><ispartof>International journal of legal medicine, 2021-07, Vol.135 (4), p.1471-1476</ispartof><rights>The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature 2021</rights><rights>The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature 2021.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c375t-2ce88cae95403e99809d35f10335669c9d8a09a7ecf8b7bd108c6c208f14fa793</citedby><cites>FETCH-LOGICAL-c375t-2ce88cae95403e99809d35f10335669c9d8a09a7ecf8b7bd108c6c208f14fa793</cites><orcidid>0000-0003-1488-4110</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00414-021-02594-z$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00414-021-02594-z$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27922,27923,41486,42555,51317</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33928430$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hong, Young-ki</creatorcontrib><creatorcontrib>Kim, Young-Hoon</creatorcontrib><creatorcontrib>Lee, Jin-Moo</creatorcontrib><creatorcontrib>Yoo, Hye Hyun</creatorcontrib><creatorcontrib>Choi, Sun-Ok</creatorcontrib><creatorcontrib>Kang, Mi Sun</creatorcontrib><title>Characterization of in vitro phase I metabolites of methamnetamine in human liver microsomes by liquid chromatography-quadrupole time-of-flight mass spectrometry</title><title>International journal of legal medicine</title><addtitle>Int J Legal Med</addtitle><addtitle>Int J Legal Med</addtitle><description>N
-Methyl-1-(naphthalen-2-yl)propan-2-amine (methamnetamine, PAL-1046) is an amphetamine-based new psychoactive substance (NPS). Methamnetamine has been reported to cause excessive release of serotonin, and it is classified as an empathogen or entactogen. It is not regulated as a controlled substance in most countries, and there are no studies on its metabolism. In this study, in vitro phase I metabolism of methamnetamine in human liver microsomes (HLM) and flavin-containing monooxygenase (FMO) was investigated by liquid chromatography-quadrupole time-of-flight mass spectrometry (LC-Q-TOF/MS). Eight metabolites of methamnetamine were identified and were structurally characterized achieved by a combination of accurate mass analysis and tandem mass spectrometry. The identified metabolic processes include
N
-demethylation,
N
-hydroxylation, aromatic hydroxylation, and a combination of these processes.
N
-Hydroxylated metabolites were confirmed based on expressed FMOs. The major metabolite was formed from methamnetamine via hydroxylation of the naphthalene ring after the in vitro phase I process. These results could help detect methamnetamine ingestion by NPS abusers.</description><subject>Amphetamines</subject><subject>Chromatography</subject><subject>Forensic Medicine</subject><subject>Hydroxylation</subject><subject>Ingestion</subject><subject>Ions</subject><subject>Liquid chromatography</subject><subject>Liver</subject><subject>Mass spectrometry</subject><subject>Medical Law</subject><subject>Medicine</subject><subject>Medicine & Public Health</subject><subject>Metabolism</subject><subject>Metabolites</subject><subject>Naphthalene</subject><subject>Quadrupoles</subject><subject>Scientific imaging</subject><subject>Serotonin</subject><subject>Short Communication</subject><subject>Spectroscopy</subject><issn>0937-9827</issn><issn>1437-1596</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNp9kcFu1DAQhi1ERZfCC3BAlrhwMbXjOLGPaFWgUiUu9Bw5znjjKo6ztlNp9214U7zdAhIHDpY9M9_Mb82P0DtGPzFK2-tEac1qQitWjlA1Ob5AG1bzljChmpdoQ1V5K1m1l-h1Sg-UsrZpxSt0ybmqZM3pBv3cjjpqkyG6o84uzDhY7Gb86HIMeBl1AnyLPWTdh8llSKd6CUft55L0boYTPq5ez3hyjxCxdyaGFHxh-0PJ7Vc3YDPG4HUOu6iX8UD2qx7iuoQJcHYeSLDETm43Zux1SjgtYIp-0YmHN-jC6inB2-f7Ct1_ufmx_Ubuvn-93X6-I4a3IpPKgJRGgxI15aCUpGrgwjLKuWgaZdQgNVW6BWNl3_YDo9I0pqLSstrqVvEr9PE8d4lhv0LKnXfJwDTpGcKaukoUWLCqqQr64R_0IaxxLr8rVM1Y2a2QharO1GkdKYLtlui8joeO0e5kYHc2sCsGdk8GdsfS9P559Np7GP60_HasAPwMpFKadxD_av9n7C9IDKrA</recordid><startdate>20210701</startdate><enddate>20210701</enddate><creator>Hong, Young-ki</creator><creator>Kim, Young-Hoon</creator><creator>Lee, Jin-Moo</creator><creator>Yoo, Hye Hyun</creator><creator>Choi, Sun-Ok</creator><creator>Kang, Mi Sun</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>0-V</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8AM</scope><scope>8AO</scope><scope>8FE</scope><scope>8FG</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>ALSLI</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BGRYB</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>HCIFZ</scope><scope>K7.</scope><scope>K9.</scope><scope>L6V</scope><scope>M0O</scope><scope>M0S</scope><scope>M1P</scope><scope>M7S</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>PTHSS</scope><scope>Q9U</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1488-4110</orcidid></search><sort><creationdate>20210701</creationdate><title>Characterization of in vitro phase I metabolites of methamnetamine in human liver microsomes by liquid chromatography-quadrupole time-of-flight mass spectrometry</title><author>Hong, Young-ki ; 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-Methyl-1-(naphthalen-2-yl)propan-2-amine (methamnetamine, PAL-1046) is an amphetamine-based new psychoactive substance (NPS). Methamnetamine has been reported to cause excessive release of serotonin, and it is classified as an empathogen or entactogen. It is not regulated as a controlled substance in most countries, and there are no studies on its metabolism. In this study, in vitro phase I metabolism of methamnetamine in human liver microsomes (HLM) and flavin-containing monooxygenase (FMO) was investigated by liquid chromatography-quadrupole time-of-flight mass spectrometry (LC-Q-TOF/MS). Eight metabolites of methamnetamine were identified and were structurally characterized achieved by a combination of accurate mass analysis and tandem mass spectrometry. The identified metabolic processes include
N
-demethylation,
N
-hydroxylation, aromatic hydroxylation, and a combination of these processes.
N
-Hydroxylated metabolites were confirmed based on expressed FMOs. The major metabolite was formed from methamnetamine via hydroxylation of the naphthalene ring after the in vitro phase I process. These results could help detect methamnetamine ingestion by NPS abusers.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><pmid>33928430</pmid><doi>10.1007/s00414-021-02594-z</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-1488-4110</orcidid></addata></record> |
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| ispartof | International journal of legal medicine, 2021-07, Vol.135 (4), p.1471-1476 |
| issn | 0937-9827 1437-1596 |
| language | eng |
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| source | HeinOnline Law Journal Library; SpringerLink Journals - AutoHoldings |
| subjects | Amphetamines Chromatography Forensic Medicine Hydroxylation Ingestion Ions Liquid chromatography Liver Mass spectrometry Medical Law Medicine Medicine & Public Health Metabolism Metabolites Naphthalene Quadrupoles Scientific imaging Serotonin Short Communication Spectroscopy |
| title | Characterization of in vitro phase I metabolites of methamnetamine in human liver microsomes by liquid chromatography-quadrupole time-of-flight mass spectrometry |
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