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7,8‐Dihydr­oxy‐4‐propyl‐1,2,3,4,4a,5,6,10b‐octa­hydro­benzo[f]quinolinium bromide monohydrate,a dopamine agonist
Authors:Andrew Hempel  Lilian Y Y Ma  Arthur Camerman  Donald Mastropaolo  Norman Camerman
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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