What are the left two lanes in the third and fourth pic?
I'll go back through my notes but I think that bufotenine did stain the plate even without UV. Bufotenine I think was at very similar height to DMT in that particular TLC eluent but you could see a slight difference if you put DMT at the same lane.
So for example you could do a plate:
1- DMT reference (known dmt-containing plant or extract)
2- Possible bufo-containing plant that might be mistaken with DMT
3- Same as 2 but with a bit of the DMT reference added on top on the same lane.
You could see if it does form 2 spots or not.
Another thing you can do is add reagents to the spots on the plate, I will check back on my notes but im pretty sure pdmab-ts / hoffman reagent could tell dmt and bufotenine appart.
Another thing is that yopo is generally found with bufotenine only, not dmt.. seems d. pulchellum is also mostly bufotenine, so it would make sense the visible spot in both and similar DMT height.
5-MeO-DMT too was at similar height but also was slightly different so you could see the two spots just above each other.
You need to have your sample diluted so that its not forming a very big spot that probably will "mask" the two different alkaloids since they have similar Rf's, specially in the pulchellum case.
I don't have pure bufotenine at hand but I do have some pure 5-MeO-DMT that I could use to test solubility and test for degradation in different conditions. What should be tested?
Btw thanks a lot for doing these experiments and posting the results, this is def very cool to see