It might, esters are non-polar enough to make their way through the BBB in reasonable amounts, but I am more curious as to whether that would interfere with 5HT2 binding or not. In fact the propionyl analogue probably has greater lipophilicity than the acetyl. The further up you go with the size of the carbon chain of esters, the greater the LogD and theoretical BBB permeation, however you also run the risk of the compound being too large to effectively fit into the 5HT2 receptor, as well as the compound being unable to be metabolized into the indolol. That would make for a drug that got into the brain very well, but did shit all once it got there.
4-AcO-DiPT was a weird one for me in that it took me damned near forever after taking it to sleep, despite the fact that I wasn't very much intoxicated, indicating to me that the 4-AcO group may have prolonged the action of the parent compound (either through metabolism or avoiding clearance or both).