Its worth a try if you're up for it.
In the TiHKAL entry Shulgin doesn't detail what exactly he meant when he said it "verged on being painful". Whether he meant actual physiological pain in the ears or just a sort of 'nails on chalkboard' response to sound it's unclear. I felt quite a bit of MDMA in DiPT, it was very emotional and connective so I think there's probably room for some fruitful experimentation there.
I think it's important to be a little cautious with this chemical because of it's unique action and the fact that there's a unanimous report of that strange sensation in the inner/middle ear area which lends itself to some sort of actual physiological change. Throwing other chemicals into the mix could complicate that change, but that's just my personal speculation. I certainly felt an apt 'slot' for DMT and LSD with DiPT, and I intend to explore those roads. If the MDMA/DiPT combo calls to you, by all means answer it but tread lightly! start low!
