Reaction of histamine with o-phthalaldehyde: isolation and analysis of the fluorophore |
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Authors: | A.L. Rönnberg C. Hansson T. Drakenberg R. Håkanson |
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Affiliation: | 1. Department of Pharmacology, University of Lund, Sölvegatan 10, S-223 62 Lund, Sweden;2. Department of Physical Chemistry II, University of Lund, Sölvegatan 10, S-223 62 Lund, Sweden |
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Abstract: | Histamine reacts with o-phthalaldehyde (OPT) to form colored as well as highly fluorescent derivatives. After large-scale synthesis, the chromophores were eliminated and the pale yellowish fluorophore was isolated by a series of chromatographic steps, followed by semipreparative high-performance liquid chromatography. Structural analysis of the fluorophore was performed using NMR and mass spectrometry. The isolated fluorophore was found to be a condensation product of 2 molecules of OPT and 1 molecule of histamine, arranged to form a complex dihydrophenantroline derivative with a quaternary amine group. The molecular weight of its chloride salt was 379.5. It was shown that the fluorophore exists in aqueous milieu as an equilibrium between three isomers. |
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