The aim of this study was to prepare new crystalline salts of cyamemazine, an antipsychotic drug, with dicarboxylic acids, and compare their thermal stabilities, dissolution properties, and structural features. Among the eight acids investigated, we report novel salts with four acids, namely, L-malic, malonic, succinic, and fumaric acids. The study was extended to include the already known maleate and marketed L-tartrate salts as well. To the best of our knowledge, this is the first-ever study of the solid-state landscape of cyamemazine and report of its crystal structure. A rare phenomenon of kryptoracemic behavior exhibited by the L-tartrate, L-malate, and maleate salts adds an interesting perspective to this study since one of these salts is currently marketed. A powder second harmonic generation setup was developed as a tool to identify the kryptoracemates of this drug, and how this would help potentially in the production of specific solid forms of drugs is discussed. The dissolution rate measurement of the prepared salts confirmed that the succinate, L-malate, and malonate salts dissolve better and all of the new salts display improved thermal stability than the free base of the API, suggesting great potential for some of the candidates to be used for marketing purposes.
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