Matthew 27:3

τότε connects the repentance of Judas with the leading of Jesus away to Pilate which he regarded as sealing his fate. What happened was but the natural result of the apprehension which he himself had brought about, and he doubtless had the natural issue in view at the moment of apprehension. But reaction had set in, partly as a matter of course in a “two-souled” man, partly at sight of the grim reality: his Master led to death by his assistance (ὅτι κατεκρίθη). μεταμεληθεὶς, regretting, rueing what he had done: wishing it were undone. ἀπέστρεψε (ἔστρεψε W.H [148] as in Isaiah 38:8), returned the thirty pieces of silver, a sign in such a nature that the repentance as far as it went was very real.

[148] Westcott and Hort.