New (old) 4-Meo-tryptamine route?

[Learnbydoing]

Before I post this question, I'd like to say that I already read Rhodium's method, so I know about it.  Anyway, when swim was glanicng through his o-chem book, he realized that a 24 hour aqueous reflux of melatonin in excess NaOH should produce 5-Meo-Tryptamine.  Has anyone done this?  What are the yields?  And all swim would have to do is then collect the 5-Meo-T and expose it to MeI to get 5-MeO-dmt, correct?

[Rhodium]

Melatonin to 5-MeO-Tryptamine:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/mexamine.html

You cannot just add MeI to 5-MeO-Tryptamine to get 5-MeO-DMT, you will get 5-MeO-DMT Methiodide (N,N,N-Trimethyl-5-MeO-tryptammonium iodide) instead, as there is nothing that keeps a third MeI molecule from adding to the nitrogen (no, it doesn't help using only a small amount of MeI).

This problem with overalkylation of tryptamines has been discussed extensively in the tryptamine forum before. See for example

Post 126957

(Lilienthal: "Breath of Hoax? / PTC tryptamine alkylation on the test bench", Tryptamine Chemistry)

[armageddon]

Think u need NaOCH3 (sodium methoxide), NaBH3CN (sodium cyanoborohydride) and HCHO (formaldehyde) to affect said conversation... (see also

Post 126971

(SeeTheQue: "Re: Breath of Hoax? / PTC tryptamine alkylation on the test bench", Tryptamine Chemistry) quote:

"Anyone who wants to mess with trying to dialkylate tryptamine with MeI is free to try, but you *will* get lots of quaternary amine.  Tertiary alkyl amines are significantly more nucleophillic than primary and secondary amines, and the dimethyl is not  that sterically hindering when quaternizing.  Methylating a tertiary amine to give the ammonium is like hitting the broad side of a barn.

Look up one of the original Borch references for the NaBH3CN rxn. and go see the aliens.")

A writeup for tryptamine dimethylation with NaBH3CN/HCHO can be found at Rhod's (where else   ):

https://www.thevespiary.org/rhodium/Rhodium/chemistry/5-cn-dmt.html

  (cyano or not - same procedure..)

(am I spoonfeeding?   )

[EDIT] Oops, just realized that Rhodium already pointed to the thread to which I linked/from which I cited, too... so the link is obsolete.[/EDIT]

Greetz A