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Bruinstroop E, van der Spek AH, Boelen A

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However, the solvent and other parameters such as pH, temperature, Oxygen or the presence of cations have been suggested to influence keto-enol tautomerism, the epimerisation of the dimethylamino group in C4, facilitating the formation of typical degradation products (including epimers) of doxycycline, leading to drug inactivation (3033)