The Identification of the Urinary Metabolites of 3-(4-Methoxybenzoyl)-1-Pentylindole (RCS-4), a Novel Cannabimimetic, by Gas Chromatography-Mass Spectrometry
3-(4-Methoxybenzoyl)-1-pentylindole (RCS-4), a synthetic indole-derived cannabimimetic, was first reported to the European Monitoring Centre for Drugs and Drug Addiction via the Early Warning System by Hungarian authorities in 2010 and later identified in head shop test purchases in Ireland. Using g...
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| Veröffentlicht in: | Journal of analytical toxicology 2012-06, Vol.36 (5), p.303-311 |
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| creator | Kavanagh, Pierce Grigoryev, Andrej Melnik, Aleksandra Simonov, Anton |
| description | 3-(4-Methoxybenzoyl)-1-pentylindole (RCS-4), a synthetic indole-derived cannabimimetic, was first reported to the European Monitoring Centre for Drugs and Drug Addiction via the Early Warning System by Hungarian authorities in 2010 and later identified in head shop test purchases in Ireland. Using gas chromatography-mass spectrometry, we have identified a series of RCS-4 metabolites in urine samples from individuals admitted to hospitals with symptoms of drug intoxication. The metabolites were tentatively identified as products of (i) aromatic monohydroxylation; (ii) dihydroxylation; (iii) aromatic hydroxylation/oxidation of the N-pentyl chain to a ketone; (iv) O-demethylation; (v) O-demethylation/monohydroxylation of N-pentyl chain; (vi) O-demethylation/oxidation of the N-pentyl chain to a ketone; (vii) O-demethylation/aromatic hydroxylation/oxidation of the N-pentyl chain to a ketone; (viii) N-depentylation/aromatic monohydroxylation; and (ix) N and O-dealkylation. The parent compound was not detected. The O-demethylated metabolites were found to be the most useful metabolic markers for the identification of RCS-4 ingestion. |
| doi_str_mv | 10.1093/jat/bks032 |
| format | Article |
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Using gas chromatography-mass spectrometry, we have identified a series of RCS-4 metabolites in urine samples from individuals admitted to hospitals with symptoms of drug intoxication. The metabolites were tentatively identified as products of (i) aromatic monohydroxylation; (ii) dihydroxylation; (iii) aromatic hydroxylation/oxidation of the N-pentyl chain to a ketone; (iv) O-demethylation; (v) O-demethylation/monohydroxylation of N-pentyl chain; (vi) O-demethylation/oxidation of the N-pentyl chain to a ketone; (vii) O-demethylation/aromatic hydroxylation/oxidation of the N-pentyl chain to a ketone; (viii) N-depentylation/aromatic monohydroxylation; and (ix) N and O-dealkylation. The parent compound was not detected. The O-demethylated metabolites were found to be the most useful metabolic markers for the identification of RCS-4 ingestion.</description><identifier>ISSN: 0146-4760</identifier><identifier>EISSN: 1945-2403</identifier><identifier>DOI: 10.1093/jat/bks032</identifier><identifier>PMID: 22582265</identifier><identifier>CODEN: JATOD3</identifier><language>eng</language><publisher>Niles, IL: Oxford University Press</publisher><subject>Adult ; Aromatics ; Biomarkers - urine ; Cannabinoids - chemistry ; Cannabinoids - urine ; Drug addiction ; Female ; Gas chromatography ; Gas Chromatography-Mass Spectrometry - methods ; Head ; Hospitals ; Humans ; Hydroxylation ; Indoles - chemistry ; Indoles - urine ; Intoxication ; ketones ; Male ; Mass spectroscopy ; Metabolites ; Oxidation ; Oxidation-Reduction ; Street Drugs - analysis ; Substance Abuse Detection - methods ; Urine ; Young Adult</subject><ispartof>Journal of analytical toxicology, 2012-06, Vol.36 (5), p.303-311</ispartof><rights>The Author [2012]. Published by Oxford University Press. All rights reserved. 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Using gas chromatography-mass spectrometry, we have identified a series of RCS-4 metabolites in urine samples from individuals admitted to hospitals with symptoms of drug intoxication. The metabolites were tentatively identified as products of (i) aromatic monohydroxylation; (ii) dihydroxylation; (iii) aromatic hydroxylation/oxidation of the N-pentyl chain to a ketone; (iv) O-demethylation; (v) O-demethylation/monohydroxylation of N-pentyl chain; (vi) O-demethylation/oxidation of the N-pentyl chain to a ketone; (vii) O-demethylation/aromatic hydroxylation/oxidation of the N-pentyl chain to a ketone; (viii) N-depentylation/aromatic monohydroxylation; and (ix) N and O-dealkylation. The parent compound was not detected. The O-demethylated metabolites were found to be the most useful metabolic markers for the identification of RCS-4 ingestion.</description><subject>Adult</subject><subject>Aromatics</subject><subject>Biomarkers - urine</subject><subject>Cannabinoids - chemistry</subject><subject>Cannabinoids - urine</subject><subject>Drug addiction</subject><subject>Female</subject><subject>Gas chromatography</subject><subject>Gas Chromatography-Mass Spectrometry - methods</subject><subject>Head</subject><subject>Hospitals</subject><subject>Humans</subject><subject>Hydroxylation</subject><subject>Indoles - chemistry</subject><subject>Indoles - urine</subject><subject>Intoxication</subject><subject>ketones</subject><subject>Male</subject><subject>Mass spectroscopy</subject><subject>Metabolites</subject><subject>Oxidation</subject><subject>Oxidation-Reduction</subject><subject>Street Drugs - analysis</subject><subject>Substance Abuse Detection - methods</subject><subject>Urine</subject><subject>Young Adult</subject><issn>0146-4760</issn><issn>1945-2403</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0c1u1DAUBWALUdGhsOEBkDdIU1RT_8XOLFEEpVILiLbr6Dpzw7gkcbA9iPAuvCupZkp3sLJ0_OlY8iHkheBvBF-p01vIp-5b4ko-Igux0gWTmqvHZMGFNkxbww_J05RuORemNOoJOZSyKKU0xYL8vt4gPV_jkH3rG8g-DDS0NM_pTfQDxIleYgYXOp8x3V0pttRszjbh5-Rw-BWm7pgJ9nmumDo_rEOHdPmlumL6-IQC_Rh-YEcrGAZwvvc9Zt-cUDfRM0i02sTQQw5fI4ybiV1CSvRqxCbPMeY4PSMHLXQJn-_PI3Lz_t119YFdfDo7r95esEYpIRlqXKuGmxKVQ2VR26J1BnTbIm9aa6FAU1pZCGm0Kwuj1o6DkK2VAM6VVh2R5a53jOH7FlOue58a7DoYMGxTLaSVVpdCF_-nXChrCq3Kmb7e0SaGlCK29Rh9P3_pjOq75ep5uXq33Ixf7nu3rsf1X3o_1Qxe7QGkBro2wtD49OCKlVRamAcXtuO_HvwDc9KukQ</recordid><startdate>20120601</startdate><enddate>20120601</enddate><creator>Kavanagh, Pierce</creator><creator>Grigoryev, Andrej</creator><creator>Melnik, Aleksandra</creator><creator>Simonov, Anton</creator><general>Oxford University Press</general><general>Preston Publications</general><scope>IQODW</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>7X8</scope><scope>7U7</scope><scope>C1K</scope></search><sort><creationdate>20120601</creationdate><title>The Identification of the Urinary Metabolites of 3-(4-Methoxybenzoyl)-1-Pentylindole (RCS-4), a Novel Cannabimimetic, by Gas Chromatography-Mass Spectrometry</title><author>Kavanagh, Pierce ; Grigoryev, Andrej ; Melnik, Aleksandra ; Simonov, Anton</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3312-e4ed3c068e3be37e475fb6a4ffe0cf77a5e687251264b8563db0a12f72aabb873</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Adult</topic><topic>Aromatics</topic><topic>Biomarkers - urine</topic><topic>Cannabinoids - chemistry</topic><topic>Cannabinoids - urine</topic><topic>Drug addiction</topic><topic>Female</topic><topic>Gas chromatography</topic><topic>Gas Chromatography-Mass Spectrometry - methods</topic><topic>Head</topic><topic>Hospitals</topic><topic>Humans</topic><topic>Hydroxylation</topic><topic>Indoles - chemistry</topic><topic>Indoles - urine</topic><topic>Intoxication</topic><topic>ketones</topic><topic>Male</topic><topic>Mass spectroscopy</topic><topic>Metabolites</topic><topic>Oxidation</topic><topic>Oxidation-Reduction</topic><topic>Street Drugs - analysis</topic><topic>Substance Abuse Detection - methods</topic><topic>Urine</topic><topic>Young Adult</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kavanagh, Pierce</creatorcontrib><creatorcontrib>Grigoryev, Andrej</creatorcontrib><creatorcontrib>Melnik, Aleksandra</creatorcontrib><creatorcontrib>Simonov, Anton</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Toxicology Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><jtitle>Journal of analytical toxicology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kavanagh, Pierce</au><au>Grigoryev, Andrej</au><au>Melnik, Aleksandra</au><au>Simonov, Anton</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The Identification of the Urinary Metabolites of 3-(4-Methoxybenzoyl)-1-Pentylindole (RCS-4), a Novel Cannabimimetic, by Gas Chromatography-Mass Spectrometry</atitle><jtitle>Journal of analytical toxicology</jtitle><addtitle>J Anal Toxicol</addtitle><date>2012-06-01</date><risdate>2012</risdate><volume>36</volume><issue>5</issue><spage>303</spage><epage>311</epage><pages>303-311</pages><issn>0146-4760</issn><eissn>1945-2403</eissn><coden>JATOD3</coden><abstract>3-(4-Methoxybenzoyl)-1-pentylindole (RCS-4), a synthetic indole-derived cannabimimetic, was first reported to the European Monitoring Centre for Drugs and Drug Addiction via the Early Warning System by Hungarian authorities in 2010 and later identified in head shop test purchases in Ireland. Using gas chromatography-mass spectrometry, we have identified a series of RCS-4 metabolites in urine samples from individuals admitted to hospitals with symptoms of drug intoxication. The metabolites were tentatively identified as products of (i) aromatic monohydroxylation; (ii) dihydroxylation; (iii) aromatic hydroxylation/oxidation of the N-pentyl chain to a ketone; (iv) O-demethylation; (v) O-demethylation/monohydroxylation of N-pentyl chain; (vi) O-demethylation/oxidation of the N-pentyl chain to a ketone; (vii) O-demethylation/aromatic hydroxylation/oxidation of the N-pentyl chain to a ketone; (viii) N-depentylation/aromatic monohydroxylation; and (ix) N and O-dealkylation. The parent compound was not detected. 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| subjects | Adult Aromatics Biomarkers - urine Cannabinoids - chemistry Cannabinoids - urine Drug addiction Female Gas chromatography Gas Chromatography-Mass Spectrometry - methods Head Hospitals Humans Hydroxylation Indoles - chemistry Indoles - urine Intoxication ketones Male Mass spectroscopy Metabolites Oxidation Oxidation-Reduction Street Drugs - analysis Substance Abuse Detection - methods Urine Young Adult |
| title | The Identification of the Urinary Metabolites of 3-(4-Methoxybenzoyl)-1-Pentylindole (RCS-4), a Novel Cannabimimetic, by Gas Chromatography-Mass Spectrometry |
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