Abstract Recently it was reported that a series of 8-benzyloxycaffeine analogues are potent reversible inhibitors of human monoamine oxidase (MAO) A and B. In an attempt to discover additional C8 oxy substituents of caffeine that lead to potent MAO inhibition, a series of related 8-aryl-and alkyloxycaffeine analogues were synthesized and their MAO-A and-B inhibition potencies were compared to those of the 8-benzyloxycaffeines. The results ...