Douglas did a nice analysis and very through experiment. However, Pliny does state that she dropped the earring into the wine, no mention of crushing. With all due respect, can you see Cleopatra seducing Mark Anthony with a mortar and pestle in hand.
From Douglas's blog: What would have been Cleopatra?s solution? She could not wait for the pearl to dissolve in wine nor vinegar, so the obvious solution was to pound and pulverize the pearl and pour the ?pearl dust? into the wine, ready to be gulped down and become the ?World?s Most Expensive Dinner?.
While I offered the suggestion that Cleopatra did a slight of hand switch, there might be a simpler solution. When we think about big pearls, we're thinking 12-15 mm. But the pearls of Roman times had to have been smaller. The Roman writers describe pearl earrings made up of 3 pearls, so maybe we're talking of 5 mm, which Cleopatra could certainly gulp down.