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. 2017 Oct 9;22(10):1615.
doi: 10.3390/molecules22101615.

Solid-State Form Characterization of Riparin I

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Free PMC article

Solid-State Form Characterization of Riparin I

Elisana Afonso de Moura et al. Molecules. .
Free PMC article

Abstract

Riparin I is an alkamide with potential anxiolytic activity in preclinical studies. The characterization and understanding of solid-state properties play an importance role in drug development. For this work, the solid state of five riparin I batches (RIP-1, RIP-2, RIP-3, RIP-4, and RIP-5), obtained by the same synthesis process, were characterized by Scanning Electron Microscopy (SEM), Differential Scanning Calorimetry (DSC), DSC-photovisual, Thermogravimetry (TG), Fourier Transform Infrared (FTIR), Pyrolysis (Pyr-GC/MS), X-ray Powder Diffraction (PXRD), and Solid-State Nuclear Magnetic Resonance (ssNMR) techniques. Batches of riparin I with different crystal habits resulting in crystallization impurities were observed, which can be attributed to the presence of triethylamine. The main differences were observed by DSC, PXRD, and ssNMR analysis. DSC curves of RIP-2 and RIP-3 presented endothermic peaks at different temperatures of fusion, which can be attributed to the mixture of different crystalline forms. PXRD and ssNMR results confirmed crystallinity differences. The results offer evidence of the importance of controlling the reproducibility of the synthesis in order to obtain the adequate morphology for therapeutic efficacy and avoiding future problems in quality control of riparin I products.

Keywords: pharmaceutical analysis; riparin I; solid-state characterization.

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Scanning electron microscopic photographs of riparin I batches.
Figure 2
Figure 2
DSC curves of riparin I batches at the heating rate of 2.0 °C·min−1.
Figure 3
Figure 3
DSC-Photovisual of RIP-1, RIP-2, RIP-3, RIP-4, and RIP-5 samples in the heating 400 rate of 10 °C·min−1.
Figure 4
Figure 4
Dynamic thermogravimetric curves of riparin batches at the heating rate of 10.0 °C·min−1.
Figure 5
Figure 5
FTIR spectra of riparin batches.
Figure 6
Figure 6
Pyrograms obtained from riparin at the temperatures of 250.0 °C (column (A)) and 500.0 °C (column (B)), showing the peak corresponding to riparin I and the product ion mass spectra of riparin I and triethylamine (column (C)—bottom of the figure).
Figure 7
Figure 7
PXRD patterns of riparin I batches. The (*) show characteristic diffraction pattern for each lot.
Figure 8
Figure 8
Solid-state 13C-NMR spectra of riparin I physical forms. The (*) show characteristic peak corresponding of triethylamine.

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