Yeh I think Yuremamine was said to be fully destroyed during regular extractions - its a giant molecule so there are surely many ways how it can break apart upon bad conditions.

And who ever would want to do a 4 weeks cold Methanol extraction, except if he definetly just wants to get the Yuremamine ? xD

Ok here is the predicted NMR of Yuremamine and I think especially the Signals at the highest PPMs aren't shown in any spectrum. Therefore I would say no Yuremamine here:

H NMR 8,5 +

C NMR 135 +

don't show up

(but actually also that other ones are missing)

1H-NMR:

13C-NMR:

And for the Indol-H:

Yes thats really a possibility, this would solve that puzzle, but I was very distracted by the Prediction of Chemdraw Ultra and Mestrenova 12, who both put them between 9 and 10.

But yeh ... those Protons are always not that precisely calculated to it may be possible and as I said this would raise the purity of the samples by far!

Another reason why I discarded to write this down is that other spectra of Tryptamines at Databases have measured that Signal also at way higher PPMs, just as Chemdraw Ultra / Mestrenova would have predicted ... see here:

The NH Signal (A) is the most left one at 11,11 PPM (SDBS database)

EDIT: YES leratiomyces is right! it is the indolic proton. I already corrected it in all the pictures now.