{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,16]],"date-time":"2025-10-16T20:47:48Z","timestamp":1760647668436,"version":"build-2065373602"},"reference-count":14,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2022,8,23]],"date-time":"2022-08-23T00:00:00Z","timestamp":1661212800000},"content-version":"am","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2022,8,23]],"date-time":"2022-08-23T00:00:00Z","timestamp":1661212800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000199","name":"U.S. Department of Agriculture","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100000199","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100005825","name":"National Institute of Food and Agriculture","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100005825","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Drug Testing and Analysis"],"published-print":{"date-parts":[[2023,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Based on structural similarities and equine administration experiments, Barbarin, 5\u2010phenyl\u20102\u2010oxazolidinethione from <jats:italic>Brassicaceae<\/jats:italic> plants, is a possible source of equine urinary identifications of aminorex, (<jats:italic>R,S<\/jats:italic>)\u20105\u2010phenyl\u20104,5\u2010dihydro\u20101,3\u2010oxazol\u20102\u2010amine, an amphetamine\u2010related US Drug Enforcement Administration (DEA) controlled substance considered illegal in sport horses. We now report the synthesis and certification of <jats:italic>d<\/jats:italic><jats:sub>5<\/jats:sub>\u2010barbarin to facilitate research on the relationship between plant barbarin and such aminorex identifications. <jats:italic>D<\/jats:italic><jats:sub>5<\/jats:sub>\u2010barbarin synthesis commenced with production of <jats:italic>d<\/jats:italic><jats:sub>5<\/jats:sub>\u20102\u2010oxo\u20102\u2010phenylacetaldehyde oxime (<jats:italic>d<\/jats:italic><jats:sub>5<\/jats:sub>\u2010oxime) from <jats:italic>d<\/jats:italic><jats:sub>5<\/jats:sub>\u2010acetophenone via butylnitrite in an ethoxide\/ethanol solution. This <jats:italic>d<\/jats:italic><jats:sub>5<\/jats:sub>\u2010oxime was then reduced with lithium aluminum hydride (LiAlH<jats:sub>4<\/jats:sub>) to produce the corresponding <jats:italic>d<\/jats:italic><jats:sub>5<\/jats:sub>\u20102\u2010amino\u20101\u2010phenylethan\u20101\u2010ol (<jats:italic>d<\/jats:italic><jats:sub>5<\/jats:sub><jats:italic>\u2010<\/jats:italic>phenylethanolamine). Final ring closure of the <jats:italic>d<\/jats:italic><jats:sub>5<\/jats:sub>\u2010phenylethanolamine was performed by the addition of carbon disulfide (CS<jats:sub>2<\/jats:sub>) with pyridine. The reaction product was purified by recrystallization and presented as a stable white crystalline powder. Proton NMR spectroscopy revealed a triplet at 5.88\u2009ppm for one proton, a double doublet at 3.71\u2009ppm for one proton, and double doublet at 4.11\u2009ppm for one proton, confirming <jats:italic>d<\/jats:italic><jats:sub>5<\/jats:sub>\u2010barbarin as the product. Further characterization by high resolution mass spectrometry supports the successful synthesis of <jats:italic>d<\/jats:italic><jats:sub>5<\/jats:sub>\u2010barbarin. Purity of the recrystallized product was ascertained by High Performance Liquid Chromatography (HPLC) to be greater than 98%. Together, we have developed the synthesis and full characterization of <jats:italic>d<\/jats:italic><jats:sub>5<\/jats:sub>\u2010barbarin for use as an internal standard in barbarin\u2010related and equine forensic research.<\/jats:p>","DOI":"10.1002\/dta.3357","type":"journal-article","created":{"date-parts":[[2022,8,17]],"date-time":"2022-08-17T02:36:37Z","timestamp":1660703797000},"page":"42-46","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Synthesis and characterization of <i>d<\/i><sub>5<\/sub>\u2010barbarin for use in barbarin\u2010related research"],"prefix":"10.1002","volume":"15","author":[{"given":"Sucheta","family":"Kudrimoti","sequence":"first","affiliation":[{"name":"The Department of Veterinary Science and the Maxwell H. Gluck Equine Research Center and the Department of Toxicology and Cancer Biology University of Kentucky  Lexington Kentucky USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9795-3689","authenticated-orcid":false,"given":"Jacob","family":"Machin","sequence":"additional","affiliation":[{"name":"The Department of Veterinary Science and the Maxwell H. Gluck Equine Research Center and the Department of Toxicology and Cancer Biology University of Kentucky  Lexington Kentucky USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Adedamola S.","family":"Arojojoye","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Kentucky  Lexington Kentucky USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Samuel G.","family":"Awuah","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Kentucky  Lexington Kentucky USA"},{"name":"Center for Pharmaceutical Research and Innovation, College of Pharmacy and Department of Pharmaceutical Sciences, College of Pharmacy University of Kentucky  Lexington Kentucky USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rodney","family":"Eisenberg","sequence":"additional","affiliation":[{"name":"Frontier BioPharm, LLC  Richmond Kentucky USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Clara","family":"Fenger","sequence":"additional","affiliation":[{"name":"Equine Integrated Medicine  Georgetown Kentucky USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"George","family":"Maylin","sequence":"additional","affiliation":[{"name":"New York Drug Testing and Research Program  Ithaca New York USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andreas F.","family":"Lehner","sequence":"additional","affiliation":[{"name":"Veterinary Diagnostic Lab Section of Toxicology Michigan State University  Lansing Michigan USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8506-3147","authenticated-orcid":false,"given":"Thomas","family":"Tobin","sequence":"additional","affiliation":[{"name":"The Department of Veterinary Science and the Maxwell H. Gluck Equine Research Center and the Department of Toxicology and Cancer Biology University of Kentucky  Lexington Kentucky USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2022,8,23]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.neuint.2013.11.010"},{"key":"e_1_2_8_3_1","unstructured":"ARCI Uniform Classification Guidelines for Foreign SubstancesJanuary2018(V.13.4)."},{"key":"e_1_2_8_4_1","unstructured":"TealeP BiddleS.Possible Plant Sources of Aminorex and Potential markers of Their Ingestion in the Horse. Proceeds of the 22nd International Conference of Racing Analysists and Veterinarians. Dubai UAE p140\u2013148.2018."},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365\u20102885.2008.01015.x"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.3109\/15563650.2015.1054499"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1186\/2046\u20100481\u201063\u20108\u2010498"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.aca.2009.02.033"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.3891\/acta.chem.scand.11\u20100906"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1186\/s13620\u2010019\u20100153\u20105"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1139\/v62\u2010233"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01140a060"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/0021\u20109673(76)80014\u20103"},{"key":"e_1_2_8_14_1","unstructured":"MachinJ KudrimotiS EisenbergR et al. \u201cSynthesis Characterization and Certification of Barbarin a Possible Botanical Source of Aminorex Identifications\u201d. Submitted for presentation and publication the Society of Forensic Toxicology (SOFT) Annual Meeting Oct 07\u201312 2018. Minneapolis Minnesota p 92.2018."},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.2883"}],"container-title":["Drug Testing and Analysis"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/dta.3357","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/dta.3357","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/dta.3357","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/dta.3357","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,14]],"date-time":"2025-10-14T04:50:10Z","timestamp":1760417410000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/dta.3357"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,8,23]]},"references-count":14,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2023,1]]}},"alternative-id":["10.1002\/dta.3357"],"URL":"https:\/\/doi.org\/10.1002\/dta.3357","archive":["Portico"],"relation":{},"ISSN":["1942-7603","1942-7611"],"issn-type":[{"type":"print","value":"1942-7603"},{"type":"electronic","value":"1942-7611"}],"subject":[],"published":{"date-parts":[[2022,8,23]]},"assertion":[{"value":"2022-04-19","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-08-12","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-08-23","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}