The most basic atom in caffeine is marked Nitrogen.
Provided down is the structure of Caffeine is not acidic in fact it is basic, it will raise the pH of water to some degree . It is a weak base, so the free base will exist in equilibrium with its protonated counter part.
Due to its basicity, it will be more soluble in low pH aqueous solutions then in high pH solutions. This is because in low pH solutions, caffeine would exist completely as a protonated salt, making it more hydrophilic. Despite this, caffeine is very polar and is still quite soluble in water at higher pH levels.
Out of all the four nitrogen atoms, the most basic nitrogen atom is number 1 as it's lone pair is free for donation. The other nitrogen atoms have lone pair which are involved in resonance in someway or the other.
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