Dopamine: Acid-base properties and membrane penetration capacity

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HIGHLIGHTSThe complete set of protonation constants determined for dopamine.1H NMR method and auxiliary compounds used to determine microscopic constants.Protonation species populations reflect physico-chemical behavior of catecholamines.Dopamine and 4 related compounds were studied by 1H NMR-pH titrations and a case-tailored evaluation method. The resulting acid-base properties of dopamine are quantified in terms of 3 macroscopic and 12 microscopic protonation constants and the concomitant 3 interactivity parameters. The species- and site-specific basicities are interpreted by means of inductive and shielding effects through various intra- and intermolecular comparisons. The site-specific basicities determined this way are key parameters for the prediction of pharmacokinetic behavior and receptor-binding at the molecular level.

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