Next Article in Journal
Solvent Switched Weak Interaction of a 4-Quinazolinone with a Cavitand Derivative
Previous Article in Journal
Co-Loaded Curcumin and Methotrexate Nanocapsules Enhance Cytotoxicity against Non-Small-Cell Lung Cancer Cells

Organic Salts of Pharmaceutical Impurity p-Aminophenol

Synthesis and Solid State Pharmaceutical Centre (SSPC), Bernal Institute, University of Limerick, Limerick, Ireland
PSC Biotech Limited, Blanchardstown, Dublin 15, Ireland
Department of Chemical Engineering, University of Chemistry and Technology Prague, Technická 3, 16628 Prague 6, Czech Republic
Institute of Physics ASCR, Na Slovance 2, 182 21 Praha 8, Czech Republic
Author to whom correspondence should be addressed.
Molecules 2020, 25(8), 1910;
Received: 12 March 2020 / Revised: 11 April 2020 / Accepted: 18 April 2020 / Published: 21 April 2020
(This article belongs to the Section Medicinal Chemistry)
The presence of impurities can drastically affect the efficacy and safety of pharmaceutical entities. p-Aminophenol (PAP) is one of the main impurities of paracetamol (PA) that can potentially show toxic effects such as maternal toxicity and nephrotoxicity. The removal of PAP from PA is challenging and difficult to achieve through regular crystallization approaches. In this regard, we report four new salts of PAP with salicylic acid (SA), oxalic acid (OX), l-tartaric acid (TA), and (1S)-(+)-10-camphorsulfonic acid (CSA). All the PAP salts were analyzed using single-crystal X-ray diffraction, powder X-ray diffraction, infrared spectroscopy, differential scanning calorimetry, and thermogravimetric analysis. The presence of minute amounts of PAP in paracetamol solids gives a dark color to the product that was difficult to remove through crystallization. In our study, we found that the addition of small quantities of the aforementioned acids helps to remove PAP from PA during the filtration and washings. This shows that salt formation could be used to efficiently remove challenging impurities. View Full-Text
Keywords: paracetamol; 4-aminophenol or p-aminophenol; salt; impurity removal; particle size paracetamol; 4-aminophenol or p-aminophenol; salt; impurity removal; particle size
Show Figures

Figure 1

MDPI and ACS Style

Khandavilli, U.B.R.; Keshavarz, L.; Skořepová, E.; Steendam, R.R.E.; Frawley, P.J. Organic Salts of Pharmaceutical Impurity p-Aminophenol. Molecules 2020, 25, 1910.

AMA Style

Khandavilli UBR, Keshavarz L, Skořepová E, Steendam RRE, Frawley PJ. Organic Salts of Pharmaceutical Impurity p-Aminophenol. Molecules. 2020; 25(8):1910.

Chicago/Turabian Style

Khandavilli, U. B.R., Leila Keshavarz, Eliška Skořepová, René R.E. Steendam, and Patrick J. Frawley. 2020. "Organic Salts of Pharmaceutical Impurity p-Aminophenol" Molecules 25, no. 8: 1910.

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

Back to TopTop