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Synthesis and characterization of d5 -barbarin for use in barbarin-related research.
Kudrimoti, Sucheta; Machin, Jacob; Arojojoye, Adedamola S; Awuah, Samuel G; Eisenberg, Rodney; Fenger, Clara; Maylin, George; Lehner, Andreas F; Tobin, Thomas.
Afiliación
  • Kudrimoti S; 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.
  • Machin J; 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.
  • Arojojoye AS; Department of Chemistry, University of Kentucky, Lexington, Kentucky, USA.
  • Awuah SG; Department of Chemistry, University of Kentucky, Lexington, Kentucky, USA.
  • Eisenberg R; Center for Pharmaceutical Research and Innovation, College of Pharmacy and Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, Kentucky, USA.
  • Fenger C; Frontier BioPharm, LLC, Richmond, Kentucky, USA.
  • Maylin G; Equine Integrated Medicine, Georgetown, Kentucky, USA.
  • Lehner AF; New York Drug Testing and Research Program, Ithaca, New York, USA.
  • Tobin T; Veterinary Diagnostic Lab Section of Toxicology, Michigan State University, Lansing, Michigan, USA.
Drug Test Anal ; 15(1): 42-46, 2023 Jan.
Article en En | MEDLINE | ID: mdl-35975356
Based on structural similarities and equine administration experiments, Barbarin, 5-phenyl-2-oxazolidinethione from Brassicaceae plants, is a possible source of equine urinary identifications of aminorex, (R,S)-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine, an amphetamine-related US Drug Enforcement Administration (DEA) controlled substance considered illegal in sport horses. We now report the synthesis and certification of d5 -barbarin to facilitate research on the relationship between plant barbarin and such aminorex identifications. D5 -barbarin synthesis commenced with production of d5 -2-oxo-2-phenylacetaldehyde oxime (d5 -oxime) from d5 -acetophenone via butylnitrite in an ethoxide/ethanol solution. This d5 -oxime was then reduced with lithium aluminum hydride (LiAlH4 ) to produce the corresponding d5 -2-amino-1-phenylethan-1-ol (d5 -phenylethanolamine). Final ring closure of the d5 -phenylethanolamine was performed by the addition of carbon disulfide (CS2 ) 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 ppm for one proton, a double doublet at 3.71 ppm for one proton, and double doublet at 4.11 ppm for one proton, confirming d5 -barbarin as the product. Further characterization by high resolution mass spectrometry supports the successful synthesis of d5 -barbarin. 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 d5 -barbarin for use as an internal standard in barbarin-related and equine forensic research.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Protones / Aminorex Límite: Animals Idioma: En Revista: Drug Test Anal Asunto de la revista: FARMACOLOGIA Año: 2023 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Reino Unido
Texto completo
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Imprimir
XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Protones / Aminorex Límite: Animals Idioma: En Revista: Drug Test Anal Asunto de la revista: FARMACOLOGIA Año: 2023 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Reino Unido