Abstract
Aminorex is a US DEA Schedule 1 controlled substance occasionally detected in racing horses. A number of aminorex identifications in sport horses were thought to have been caused by exposure to plant sources of aminorex. Glucobarbarin, found in plants of the Brassicaceae family, has been suggested as a potential proximate chemical source by being metabolized in the plant or the horse to aminorex. In Brassicaceae, glucobarbarin is hydrolyzed by myrosinase to yield barbarin, which serves as an insect repellant and/or attractant and is structurally related to aminorex. The synthesis, purification, and characterization of barbarin is now reported for use as a reference standard in aminorex related research concerning equine urinary identifications of aminorex and also for possible use in equine administration experiments. Synthesis of barbarin was performed via ring closure between phenylethanolamine and carbon disulfide in tetrahydrofuran with the catalyst pyridine under reflux. The reaction yielded a white crystalline substance that was purified and chemically characterized as barbarin for use as a Certified Reference Standard or for studies related to equine aminorex identification.
| Original language | English |
|---|---|
| Pages (from-to) | 1477-1482 |
| Number of pages | 6 |
| Journal | Drug Testing and Analysis |
| Volume | 12 |
| Issue number | 10 |
| DOIs | |
| State | Published - Oct 1 2020 |
Bibliographical note
Funding Information:This research was made possible by research support from The Equine Health and Welfare Alliance, Inc, Versailles, Kentucky, and the United States Trotting Association, Columbus, OH. Further support came from the National Institute of Food and Agriculture, US Department of Agriculture, Hatch Program under project KY014051 accession number 1010609 and also by grants from the USDA Agriculture Research Service Specific Cooperative Agreement #58-6401-2-0025 for Forage-Animal Production Research, the Kentucky Department of Agriculture and the Kentucky Thoroughbred Association Foundation and by support for the Kentucky Agricultural Experiment Station as provided by the National Institute of Food and Agriculture (NIFA) and the Commonwealth of Kentucky. Other support includes research support from The National Horsemen's Benevolent and Protective Association and the Alabama, Arizona, Arkansas, Ontario, Canada; Charles Town, WV; Florida, Indiana, Iowa, Kentucky, Louisiana, Michigan, Minnesota, Nebraska, Ohio, Oklahoma, Oregon, Pennsylvania, Tampa Bay Downs, Florida, Texas, Washington State, and West Virginia Horsemen's Benevolent and Protective Associations. Published as paper #499 from T. Tobin and the Equine Pharmacology, Therapeutics and Toxicology Program at the Maxwell H. Gluck Equine Research Center and Department of Veterinary Science, University of Kentucky.
Funding Information:
This research was made possible by research support from The Equine Health and Welfare Alliance, Inc, Versailles, Kentucky, and the United States Trotting Association, Columbus, OH. Further support came from the National Institute of Food and Agriculture, US Department of Agriculture, Hatch Program under project KY014051 accession number 1010609 and also by grants from the USDA Agriculture Research Service Specific Cooperative Agreement #58‐6401‐2‐0025 for Forage‐Animal Production Research, the Kentucky Department of Agriculture and the Kentucky Thoroughbred Association Foundation and by support for the Kentucky Agricultural Experiment Station as provided by the National Institute of Food and Agriculture (NIFA) and the Commonwealth of Kentucky. Other support includes research support from The National Horsemen's Benevolent and Protective Association and the Alabama, Arizona, Arkansas, Ontario, Canada; Charles Town, WV; Florida, Indiana, Iowa, Kentucky, Louisiana, Michigan, Minnesota, Nebraska, Ohio, Oklahoma, Oregon, Pennsylvania, Tampa Bay Downs, Florida, Texas, Washington State, and West Virginia Horsemen's Benevolent and Protective Associations. Published as paper #499 from T. Tobin and the Equine Pharmacology, Therapeutics and Toxicology Program at the Maxwell H. Gluck Equine Research Center and Department of Veterinary Science, University of Kentucky.
Funding Information:
The Equine Health and Welfare Alliance, Inc, Versailles, Kentucky, and the United States Trotting Association, Columbus, OH. National Institute of Food and Agriculture, U.S. Department of Agriculture, Hatch Program under project KY014051 accession number 1010609; USDA Agriculture Research Service Specific Cooperative Agreement #58‐6401‐2‐0025 for Forage‐Animal Production Research, the Kentucky Department of Agriculture and the Kentucky Thoroughbred Association Foundation and by support for the Kentucky Agricultural Experiment Station as provided by the National Institute of Food and Agriculture (NIFA) and the Commonwealth of Kentucky. Other support includes research support from The National Horsemen's Benevolent and Protective Association and the Alabama, Arizona, Arkansas, Ontario, Canada; Charles Town, WV; Florida, Indiana, Iowa, Kentucky, Louisiana, Michigan, Minnesota, Nebraska, Ohio, Oklahoma, Oregon, Pennsylvania, Tampa Bay Downs, Florida, Texas, Washington State, and West Virginia Horsemen's Benevolent and Protective Associations.
Publisher Copyright:
© 2020 John Wiley & Sons, Ltd.
Keywords
- Brassicaceae
- aminorex
- barbarin
- equine forensic chemistry
- synthesis
ASJC Scopus subject areas
- Analytical Chemistry
- Environmental Chemistry
- Pharmaceutical Science
- Spectroscopy