Mechanochemical Synthesis and Crystal Structure of the Lidocaine-Phloroglucinol Hydrate 1:1:1 Complex
Molecular complexation is a strategy used to modify the physicochemical or biopharmaceutical properties of an active pharmaceutical ingredient. Solvent assisted grinding is a common method used to obtain solid complexes in the form of cocrystals. Lidocaine is a drug used as an anesthetic and for the...
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MDPI AG
2018-03-01
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| Series: | Crystals |
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| Online Access: | http://www.mdpi.com/2073-4352/8/3/130 |
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| author | Nancy Evelyn Magaña-Vergara Porfirio de la Cruz-Cruz Ana Lilia Peraza-Campos Francisco Javier Martínez-Martínez Juan Saulo González-González |
| author_facet | Nancy Evelyn Magaña-Vergara Porfirio de la Cruz-Cruz Ana Lilia Peraza-Campos Francisco Javier Martínez-Martínez Juan Saulo González-González |
| author_sort | Nancy Evelyn Magaña-Vergara |
| collection | DOAJ |
| description | Molecular complexation is a strategy used to modify the physicochemical or biopharmaceutical properties of an active pharmaceutical ingredient. Solvent assisted grinding is a common method used to obtain solid complexes in the form of cocrystals. Lidocaine is a drug used as an anesthetic and for the treatment of chronic pain, which bears in its chemical structure an amide functional group able to form hydrogen bonds. Polyphenols are used as cocrystal coformers due to their ability to form O–H···X (X = O, N) hydrogen bond interactions. The objective of this study was to exploit the ability of phloroglucinol to form molecular complexes with lidocaine by liquid assisted grinding. The formation of the complex was confirmed by the shift of the O–H and C=O stretching bands in the IR spectra of the polycrystalline ground powders, suggesting the formation of O–H···O=C hydrogen bonds. Hydration of the complexes also was confirmed by IR spectroscopy and by powder X-ray diffraction. The molecular structure was determined by single crystal X-ray diffraction. |
| first_indexed | 2024-04-14T02:27:03Z |
| format | Article |
| id | doaj.art-e07b29a9438247f4942e8115ed403afb |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-04-14T02:27:03Z |
| publishDate | 2018-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-e07b29a9438247f4942e8115ed403afb2022-12-22T02:17:50ZengMDPI AGCrystals2073-43522018-03-018313010.3390/cryst8030130cryst8030130Mechanochemical Synthesis and Crystal Structure of the Lidocaine-Phloroglucinol Hydrate 1:1:1 ComplexNancy Evelyn Magaña-Vergara0Porfirio de la Cruz-Cruz1Ana Lilia Peraza-Campos2Francisco Javier Martínez-Martínez3Juan Saulo González-González4CONACyT-Facultad de Ciencias Químicas, Universidad de Colima, Km 9 Carretera Colima-Coquimatlán, Coquimatlán C.P. 28400, Colima, MexicoInstituto de Farmacobiología, Universidad de la Cañada, Carretera Teotitlán—San Antonio Nanahuatipán Km 1.7 s/n., Paraje Titlacuatitla, Teotitlán de Flores Magón, Oaxaca C.P. 68540, MexicoCONACyT-Facultad de Ciencias Químicas, Universidad de Colima, Km 9 Carretera Colima-Coquimatlán, Coquimatlán C.P. 28400, Colima, MexicoCONACyT-Facultad de Ciencias Químicas, Universidad de Colima, Km 9 Carretera Colima-Coquimatlán, Coquimatlán C.P. 28400, Colima, MexicoInstituto de Farmacobiología, Universidad de la Cañada, Carretera Teotitlán—San Antonio Nanahuatipán Km 1.7 s/n., Paraje Titlacuatitla, Teotitlán de Flores Magón, Oaxaca C.P. 68540, MexicoMolecular complexation is a strategy used to modify the physicochemical or biopharmaceutical properties of an active pharmaceutical ingredient. Solvent assisted grinding is a common method used to obtain solid complexes in the form of cocrystals. Lidocaine is a drug used as an anesthetic and for the treatment of chronic pain, which bears in its chemical structure an amide functional group able to form hydrogen bonds. Polyphenols are used as cocrystal coformers due to their ability to form O–H···X (X = O, N) hydrogen bond interactions. The objective of this study was to exploit the ability of phloroglucinol to form molecular complexes with lidocaine by liquid assisted grinding. The formation of the complex was confirmed by the shift of the O–H and C=O stretching bands in the IR spectra of the polycrystalline ground powders, suggesting the formation of O–H···O=C hydrogen bonds. Hydration of the complexes also was confirmed by IR spectroscopy and by powder X-ray diffraction. The molecular structure was determined by single crystal X-ray diffraction.http://www.mdpi.com/2073-4352/8/3/130lidocainephloroglucinolcrystal structurehydrogen bondhydrationmolecular complex |
| spellingShingle | Nancy Evelyn Magaña-Vergara Porfirio de la Cruz-Cruz Ana Lilia Peraza-Campos Francisco Javier Martínez-Martínez Juan Saulo González-González Mechanochemical Synthesis and Crystal Structure of the Lidocaine-Phloroglucinol Hydrate 1:1:1 Complex Crystals lidocaine phloroglucinol crystal structure hydrogen bond hydration molecular complex |
| title | Mechanochemical Synthesis and Crystal Structure of the Lidocaine-Phloroglucinol Hydrate 1:1:1 Complex |
| title_full | Mechanochemical Synthesis and Crystal Structure of the Lidocaine-Phloroglucinol Hydrate 1:1:1 Complex |
| title_fullStr | Mechanochemical Synthesis and Crystal Structure of the Lidocaine-Phloroglucinol Hydrate 1:1:1 Complex |
| title_full_unstemmed | Mechanochemical Synthesis and Crystal Structure of the Lidocaine-Phloroglucinol Hydrate 1:1:1 Complex |
| title_short | Mechanochemical Synthesis and Crystal Structure of the Lidocaine-Phloroglucinol Hydrate 1:1:1 Complex |
| title_sort | mechanochemical synthesis and crystal structure of the lidocaine phloroglucinol hydrate 1 1 1 complex |
| topic | lidocaine phloroglucinol crystal structure hydrogen bond hydration molecular complex |
| url | http://www.mdpi.com/2073-4352/8/3/130 |
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