Learnbydoing (Stranger)
08-14-03 02:30
No 453435
       New (old) 4-Meo-tryptamine route?     

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
(Chief Bee)
08-14-03 02:40
No 453437
       4-MeO-Tryptamine? 5-MeO-Tryptamine?     

Melatonin to 5-MeO-Tryptamine: ../rhodium /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
(Hive Bee)
07-30-04 05:45
No 522618
       tryptamine alkylation     

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 smile):

../rhodium /5-cn-dmt.html  (cyano or not - same procedure..)

(am I spoonfeeding? laugh)

[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 so the link is obsolete.[/EDIT]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
Pleased to meet you hope you get my name.
But whats puzzlin you is the nature of my game!