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?
Melatonin to 5-MeO-Tryptamine:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/mexamine.html (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 (https://www.thevespiary.org/talk/index.php?topic=12883.msg12695700#msg12695700)
(Lilienthal: "Breath of Hoax? / PTC tryptamine alkylation on the test bench", Tryptamine Chemistry)
Think u need NaOCH3 (sodium methoxide), NaBH3CN (sodium cyanoborohydride) and HCHO (formaldehyde) to affect said conversation... (see also
Post 126971 (https://www.thevespiary.org/talk/index.php?topic=12883.msg12697100#msg12697100)
(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 (https://www.thevespiary.org/rhodium/Rhodium/chemistry/5-cn-dmt.html)
(cyano or not - same procedure..)
(am I spoonfeeding? ;D )
[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 so the link is obsolete.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