PMID: 14698587Dec 31, 2003Paper

Aqueous solubility study of salts of benzylamine derivatives and p-substituted benzoic acid derivatives using X-ray crystallographic analysis

International Journal of Pharmaceutics
Henrik ParshadClaus Selch Larsen

Abstract

Twenty two p-substituted benzoic acid derivates were used to prepare salts of N-methylbenzylamine (II) and N,N-dimethylbenzylamine (III), respectively. Only five salts of (II) and two salts of (III) were obtained in a crystalline state. The solubility of these salts was orders of magnitude higher than those reported for the corresponding salts of benzylamine (I). Thermal analysis indicated that the increased solubility was caused by reduced crystal lattice energy, which was most likely due to the reduced number of strong hydrogen bonds of the salt of (II) and (III). X-ray crystallographic analysis of p-hydroxybenzoic acid salt of (I), (II) and (III) suggested that the reduced number of hydrogen bonds caused the apparent higher solubility. Further analyses of seven salts of (I) were performed. It was not possible to identify any relationship between the number of hydrogen bonds and the corresponding solubility of the salts.

References

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Citations

Nov 29, 2011·Drug Development and Industrial Pharmacy·S E DavidB R Conway
Oct 25, 2014·Drug Development and Industrial Pharmacy·Shashank JainSenshang Lin
Jan 1, 2005·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Anders Bach NielsenClaus Larsen
Oct 26, 2010·International Journal of Pharmaceutics·Yong-Mei Hao, Ke'an Li
Feb 7, 2013·Pharmacological Reviews·Hywel D WilliamsChristopher J H Porter

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