A lot has already been well answered in this thread, but I did want to chime in to say that 4-PrO-DMT has been reported to often have a similar duration if not a longer duration than 4-AcO-DMT, 4-HO-DMT, or mushrooms from the people I've known to test it, including myself. I found 4-PrO-DMT to be unique in a way that makes me wonder about the 4-glutaryloxy and other 4-substitutions, I suspect the 5, 7, and 2 positions will all be of interest on the tryptamine scaffold too, but esterifying that 4 position to an acetoxy or propionyloxy makes it seem meaningfully different.
If I had some 4-PrO-DMT on hand to waste, fuck it I'd try it with harmalas. Be sure to Shulgin climb though, start lower than you could ever imagine working and work your way up. I've had mushrooms where 90mg of harmaline and 30mg of tetrahydroharmine had me only requiring 200mg of Panaeolus cyanescens for an extensive and profound trip. On the topic of Passiflora species as an MAOI by the way, they're quite rich in tetrahydroharmine and far more clearheaded than harmine or harmaline, but you need to consume a pretty monstrous amount so I'd advise using a passiflora concentrate if you go that route.