Kynurenines are UV filters found in the human ocular lens which protect the retina from radiation damage. We report on ab initio investigations of the photochemistry of the cis and trans conformers of kynurenine and of an intramolecularly hydrogen-bonded conformer of 3-hydroxykynurenine O-β-D-glucoside. We have explored the excited-state reaction paths for several radiationless excited-state deactivation processes in kynurenines. We show that electron-driven proton-transfer processes mediated by an excited state of charge-transfer character exhibit negligible barriers and that the relevant potential-energy profiles are lower in energy than the lowest absorbing ππ* state. In these proton-transfer processes, a proton moves from one of the amino groups of kynurenine to the keto group. We also report on nonadiabatic trajectory-surface-hopping molecular-dynamics simulations for photoexcited kynurenine. These simulations show that the cis and trans conformers of kynurenine deactivate on a femtosecond-to-picosecond time scale preferably via electron-driven proton transfer from one of the amino groups to the keto group. Cis kynurenine deactivates via a ring-N-H···O═C proton-transfer process. Trans kynurenine tends to undergo trans → cis isomerization before deactivating via the same process. These results suggest that the deactivation process involving the ring-amino group in the cis conformer of kynurenine is the most efficient excited-state deactivation process in kynurenines. The joint electronic-structure calculations and dynamics simulations provide a new level of mechanistic insight into the efficient UV-filtering capacity of kynurenines.