7,8‐Dihydroxy‐4‐propyl‐1,2,3,4,4a,5,6,10b‐octahydrobenzo[f]quinolinium bromide monohydrate,a dopamine agonist |
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Authors: | Andrew Hempel Lilian Y. Y. Ma Arthur Camerman Donald Mastropaolo Norman Camerman |
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Abstract: | In the crystal structure of the title dopaminergic compound, C16H24NO2+·Br−·H2O, protonation occurs at the piperidine N atom. The piperidine ring adopts a chair conformation and the cyclohexene ring adopts a half‐chair conformation; together with the planar benzene ring, this results in a relatively planar shape for the whole molecule. Classical hydrogen bonds (N—H⋯Br, O—H⋯Br and O—H⋯O) produce an infinite three‐dimensional network. Hydrogen bonds between water molecules and Br− anions create centrosymmetric rings throughout the crystal structure. Structural comparison of the molecule with the ergoline dopamine agonist pergolide shows that it is the hydrogen‐bond‐forming hydroxy or imino group that is necessary for dopaminergic activity, rather than the presence of a phenyl or a pyrrole ring per se. |
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