Journal
CRYSTAL GROWTH & DESIGN
Volume 13, Issue 2, Pages 708-715Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cg3014249
Keywords
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Funding
- Sanofi-Aventis
- Spanish Ministry of Science and Innovation [FIS2011- 24439]
- Catalan Government [2009SGR-1251]
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3,4-Diaminopyridine is an active pharmaceutical ingredient for the treatment of Lambert Eaton myasthenic syndrome (LEMS). It is 3,4-diaminopyridine dihydrogen phosphate that has become the active ingredient of choice. As part of a larger study for the development of this drug, solid-state studies have been carried out. At room temperature, the crystals are monoclinic (C2/c). Dihydrogen phosphate anions H2PO4- form infinite chains parallel to the b axis, and these chains can be considered as macroanions (H2PO4)infinity. The organic cations form hydrogen bonds with the macroanions bridging them together. A negative thermal expansion is observed along the [103] direction in the crystal, which coincides with the direction of chains of interchanging anions and cations. The crystal packing shows similarities with the hydrogen tartrate salt as illustrated by a Hirshfeld surface analysis. This phosphate and this tartrate salt are also the two diaminopyridine salts that have been selected for therapeutic use because of their appropriate physical properties.
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