Structure of Bromopride

Rumiko TANAKA, Noriaki HIRAYAMA
2004 Analytical Sciences X-ray Structure Analysis Online  
Bromopride (4-amino-5-bromo-N-[2-(diethylamino)ethyl]-2methoxybenzamide) (Fig.1) is the bromo-analogue of metoclopramide; both are benzamide derivatives. Like metoclopramide, bromopride stimulates motility of the gastrointestinal tract, enhances gastric empyting rate, and has antiemetic properties. 1 Bromopride is used to treat a variety of gastrointestinal disorders, including nausea and vomiting, and motility disorders. The main action of bromopride is related to blockade of dopamine-2
more » ... rs in the central nervous system and gastrointestinal tract. Similar to other benzamide derivatives, gastrointestinal tract stimulation by bromopride appears to be mediated at least in part by indirect cholinergic activity. The X-ray analysis of bromopride was undertaken to disclose its inherent three-dimensional structure to understand the molecular mechanism of the drug action. Single crystals were grown from methanol/acetonitrile solution. A colorless crystal with the size of 0.25 × 0.10 × 0.08 mm was mounted on a glass fiber and used for data collection. The structure was solved by heavy-atom Patterson methods 2 and refined by a full-matrix least squares method. Non-H atoms were refined with anisotropic temperature factors. All H-atoms x79 ANALYTICAL SCIENCES 2004, VOL. 20 X-ray Structure Analysis Online The title compound, C14H22BrN3O2, is an antiemetic agent. The crystal belongs to space group P1 − with the cell dimensions a = 7.5711(6), b = 8.7500 (9) , c = 13.601(2)Å, α = 93.214(6), β = 99.940(4) and γ = 115.448(3)˚. The final R value is 0.054. The molecule does not take a fully extended conformation owing to a weak but measurable intramolecular hydrogen bond.
doi:10.2116/analscix.20.x79 fatcat:zcfi5ob5sfbzhdjht4epj2fd7a