Dopamine is a neurotransmitter that is crucial for proper functioning of the human body. The catecholamine core of dopamine has shown utility as a scaffold for numerous drugs and in other applications, like metal detection and adhesive materials. Substituents at the 6-position of the dopamine catechol core can modulate its stereoelectronic properties, the acidity of its phenolic hydroxyl groups, and the overall hydrophobicity of the molecule. To further understand the function of dopamine, a series of dopamine derivatives substituted at the 6-position of the catechol core. 6-Iododopamine, 6-carboxydopamine, and 6-acetyldopamine were synthesized from commercially available 3,4-dimethoxyphenethylamine. In order to investigate the electron donating and withdrawing ability of the substituent the Hammett constants were correlated with the <sup>1</sup>H NMR chemical shift values. The synthesis of the dopamine derivatives and Hammett correlational analysis will be discussed.

Synthesis of 6-substituted dopamine derivatives

253rd National Meeting (2017)

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