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Enantiospecific behaviour of chiral drugs in soil.

Bertin, Sophie; Yates, Kyari; Petrie, Bruce


Sophie Bertin

Kyari Yates

Bruce Petrie


Leah Morrison


The importance of stereochemistry on the behaviour and effects of chiral pharmaceutical and illicit drugs in amended agricultural soils has been over looked to date. Therefore, this study was aimed at investigating the enantiospecific behaviour of a chemically diverse range of chiral drugs including naproxen, ibuprofen, salbutamol, bisoprolol, metoprolol, propranolol, acebutolol, atenolol, chlorpheniramine, amphetamine, fluoxetine and citalopram in soil microcosms. Considerable changes of the enantiomeric composition of ibuprofen, naproxen, atenolol, acebutolol and amphetamine were observed within 56 d. This is significant as enantiomer enrichment can favour the pharmacologically active (e.g., S(−)-atenolol) or less/non-active forms of the drug (e.g., R(−)-amphetamine). Single enantiomer microcosms showed enantiospecific degradation was responsible for enantiomer enrichment of atenolol and amphetamine. However, naproxen and ibuprofen enantiomers were subject to chiral inversion whereby one enantiomer converts to its antipode. Interestingly, chiral inversion was bidirectional and this is the first time it is reported in soil. Therefore, introduction of the less active enantiomer to soil through irrigation with reclaimed wastewater or biosolids as fertiliser can result in the formation of its active enantiomer, or vice versa. This phenomenon needs considered in risk assessment frameworks to avoid underestimating the risk posed by chiral drugs in amended soils.

Journal Article Type Article
Journal Environmental pollution
Print ISSN 0269-7491
Publisher Elsevier
Peer Reviewed Peer Reviewed
Article Number 114364
Institution Citation BERTIN, S., YATES, K. and PETRIE, B. [2020]. Enantiospecific behaviour of chiral drugs in soil. Environmental pollution [online], In Press. Available from:
Keywords Pharmaceutical; Soil; Microcosm; Enantiomer; Inversion