The first opposed thumb showed up 160 million years ago, but it was probably unrelated to our lineage as it's a dinosaur. But it's being called "Monkeydactyl" anyway. It is a pterosaur to be precise, which is a winged dinosaur, in fact the first dinosaur to have evolved powered flight. https://www.birmingham.ac.uk/news/latest/2021/04/new-jurassic-flying-reptile.aspx
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