The structure and absolute configuration of (+)-3-methoxy-N-methylmorphinan (dextromethorphan) hydrobromide monohydrate

Abstract

The drug dextromethorphan crystallizes as the hydrobromide monohydrate in the orthorhombic space group P212121 with cell dimensions a = 9.217, b = 27.398, c = 7.063 A. The structure was determined by the heavy-atom technique with 2050 observed symmetry-independent reflexions collected by diffractometry. Full-matrix least-squares refinement yielded a final R value of 0.057. The absolute configuration of the cation, determined from the anomalous dispersion of Br-, was found to be opposite to that of natural (-)-morphine. In the crystal the packing of the cations is determined by hydrogen bonds; the piperidine NH ÷ acts as donor to the water molecule which in its turn forms two OH... Br-bonds running in infinite zigzag chains parallel to a.

Crystal structures of bis[(9S,13S,14S)-3-methoxy-17-methylmorphinanium] tetrachloridocobaltate and tetrachloridocuprate

“…4), leaving the shape of the organic molecule intact. The derived molecular dimensions within both structures are unexceptional and consistent with those known for similar molecules (Gylbert & Carlströ m, 1977).…”

“…A protonated form is also known in a form of the bromide salt (refcode DEXORP), in which one solvate water molecule is connected to a protonated nitrogen atom via a hydrogen bond (Gylbert & Carlströ m, 1977).…”

Submolecular partitioning of morphine hydrate based on its experimental charge density at 25 K

“…C12 is displaced by 0.04 Å from the least-squares plane. This deviation disappears in molecules without the 4,5-ether bridge, such as dextromethorphan (Gylbert & Carlströ m, 1977). Rings B and C exhibit envelope conformers, whereas ring D shows a boat conformation.…”

Structure redetermination of dextromethorphan hydrobromide monohydrate, C18H28BrNO2 – localization of hydrogen atoms

“…In continuation of our interest in metrical features of large cations [13][14][15] the structure of the title compound has been determined. While the latter has been reported previously [16], no hydrogen positions were determined which precludes discussions of inter-and intramolecular interactions. The molecular and crystal structures of tetrachlorido cuprate and cobaltate salts are known [17], as are the crystal and molecular structures of the neutral parent opioid dextromethorphan [18,19].…”