Dopamine - Chemistry

Chemistry

Structurally, dopamine belongs to the catecholamine and phenethylamine classes. The crystal structure of dopamine hydrochloride has been determined.

In the laboratory, dopamine may be synthesized by demethylation of 3,4-dimethoxyphenethylamine using hydrogen bromide:



Basicity: protonated dopamine has three acidity constants: pKa1 = 8.89 (first OH); pKa2 = 10.41 (-NH3+); pKa3 = 13.1 (second OH); the two phenolic acidity constants cannot be attributed to a specific -OH group. Because of the variables involved in pKa determination (see discussions in cited papers), other values may be found in the literature. For example, a careful set of experiments reported by Armstrong and Barlow for dopamine hydrochloride yielded these data: pKa at 25°C and 10mM concentration = 8.81 and 10.5.


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