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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

3,4-O-diacetylisoproterenol. Preparation, structure proof, and beta-receptor effect.

Direct acetylation of isoproterenol by selective O-acetylation using CH3COCl/CF3COOH was shown to lead to the formation of 2-(3,4-diacetoxyphenyl)-2-chloro-N-isopropyl-1-ethanamine and not to 3,4-O-diacetylisoproterenol. The latter was prepared by reduction of 3,4-diacetoxy(2-isopropylamino)acetophenone and its structure confirmed by IR, 1H, 13C NMR, mass spectral, and elemental analysis. The two compounds were tested for activity on beta-receptors. Efficacy and affinity on beta 1-receptors were found identical with the effect of isoproterenol. So was efficacy on beta2-receptors, while affinity was lower for the chloro compounds than for isoproterenol and diacetylisoproterenol which exhibited identical affinity.[1]


  1. 3,4-O-diacetylisoproterenol. Preparation, structure proof, and beta-receptor effect. Jakobsen, P., Treppendahl, S., Andersen, P.H., Klysner, R., Geisler, A., Teuber, L. J. Med. Chem. (1985) [Pubmed]
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