Identification of Buctopamine and Mebuctopamine, a β2 Receptor Agonist and Its Metabolite, in Swine Hair and Feed Additives
Journal
Journal of Agricultural and Food Chemistry
Journal Volume
65
Journal Issue
19
Pages
3965-3974
Date Issued
2017
Author(s)
Abstract
4-[2-(t-Butylamino)-1-hydroxyethyl]phenol (buctopamine, 4), a new β2 receptor agonist (β2-agonist), was found to be an adulterant in feed additives for swine in Taiwan, where using β2-agonists in food-production animals is prohibited. Buctopamine and its metabolite, 4-[2-(t-butylamino)-1-hydroxyethyl]-2-methoxyphenol (mebuctopamine, 2), were detected in swine hair specimens. Authentic compounds 2 and 4 were synthesized with 98.6% and 97.7% purity, respectively, as reference standards for analysis, and both compounds were more hydrophilic than ractopamine and clenbuterol. In a preliminary pharmacological evaluation, compounds 2 and 4 exhibited moderate human β2 receptor binding affinity and did not show significant affinities for the human α1, α2, β1, and β3 receptors. After addition of compounds 2-4 into the β2-agonist library, a multiresidue analysis of 26 β2-agonists by using triple quadrupole LC/MS/MS for routine screening conducted by regulatory authorities was established, in which the common limits of quantification for the 26 β2-agonists in swine feed and hair are 10 and 25 ng/g, respectively. In addition, the illegal use of buctopamine (4) has been effectively prevented. The results of this study are also useful for controlling the illegal use of new β2-agonists in food-production animals. © 2017 American Chemical Society.
Subjects
feed additive; hair; identification; metabolite; β2-agonist
Other Subjects
Additives; Animals; Binding energy; Crime; Identification (control systems); Metabolites; Feed additives; Food production; hair; Multi-residue analysis; Receptor binding; Reference standard; Regulatory authorities; Triple quadrupole; Biomolecules; beta adrenergic receptor stimulating agent; food additive; analysis; animal; animal food; chemical structure; chemistry; hair; metabolism; pig; Taiwan; Adrenergic beta-Agonists; Animal Feed; Animals; Food Additives; Hair; Molecular Structure; Swine; Taiwan
Type
journal article