doi: 10.1186/2046-0481-63-8-498.
Pemoline and tetramisole 'positives' in english racehorses following levamisole administration
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- PMID:21777496
- PMCID: PMC4177197
- DOI: 10.1186/2046-0481-63-8-498
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Pemoline and tetramisole 'positives' in english racehorses following levamisole administration
J Gutierrez et al. Ir Vet J..
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Abstract
Pemoline is a central nervous system stimulant that has been used to treat attention-deficit hyperactivity disorder and narcolepsy in humans; its identification in horses could be considered evidence of attempts to influence performance. Two recent pemoline 'positives' in English racehorses led us to review the chemical relationships between tetramisole, levamisole, aminorex and pemoline. Pemoline is a simple oxidation product of aminorex, which has been shown in the United States and elsewhere to be an equine metabolite of levamisole. Based on the clear structural relationships between aminorex and pemoline, we conclude that levamisole can metabolise to pemoline in horses and that pemoline identifications in horses post levamisole administration are likely to be associated with levamisole administration. Levamisole should not be administered to horses about to compete because of its ability to metabolise to two central nervous system stimulants, aminorex and pemoline.
Figures
Proposed conversion of Levamisole to Aminorex to Pemoline. Levamisole (1) can protonate to form intermediate 2, which can undergo alkylation of the double bond to form 3, with loss of thiirane, 3.1, to yield Aminorex 4. Aminorex can then undergo biological oxidation [O] to form Pemoline 5 (Eisenberg 2008; Ho [2]).
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