Provided are enantiomers of MDMA, such as R-MDMA and S-MDMA, and non-racemic mixtures thereof. In some embodiments, the provided mixtures comprise R-MDMA in enantiomeric excess. In other aspects, provided are methods of making such enantiomers and non-racemic mixtures, compositions thereof, and methods of using the same. In some aspects, features of the provided mixtures, compositions, and methods include improved pharmacokinetics, reduced toxicity, such as neurotoxicity, and a reduced potential for abuse. In some embodiments, improved pharmacokinetics include a reduced duration of action. In some embodiments, reduced toxicity and abuse potential result from distinct binding profiles compared to racemic MDMA, R-MDMA, or S-MDMA.