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Author: Subject: What to do with tryptamine?
clearly_not_atara
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[*] posted on 10-9-2015 at 10:42


Not sure if this is actually a legal (w/r/t the rules) discussion, but since DMT is far more easily extracted, I guess it doesn't count.

IMO you should use methyl oxalate or methyl carbonate or a similar "weak" methylating agent that won't quaternize the tryptamine. Evades all possibility of a Pictet-Spengler. Methyl oxalate is such a good candidate that I'm not sure anything else is worth mention... trimethylsulfonium bromide, maybe.
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Pumukli
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[*] posted on 11-9-2015 at 02:44


Is methyl-oxalate a methylating agent?
I think it would rather acylate the primary amine yielding tryptamine-oxalyl-amide and methanol.
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nlegaux
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[*] posted on 11-9-2015 at 10:34


You could perform a Hofmann rearrangement using the tryptamine. It would remove the α-carbon shortening the chain by one, but I am not certain how it would behave with the secondary amine in the heterocyclic ring.

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careysub
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[*] posted on 12-9-2015 at 09:21


Quote: Originally posted by zed  
Ummm. I've heard that the reagent isn't easy to come by. And, making it involves using HCN. Not fun.


It appears that sodium cyanoborohydride can be prepared without ever having free HCN by:
1. making mercury(II) cyanide from mercury(II) oxide and potassium/sodium cyanide*.
then
2. making cyanoborohydride from sodium borohydride and mercury(II) cyanide

Not without its own hazards, and I am not sure that if you have excellent fume handling equipment that it is any safer than HCN.

(*Which can be made in a laboratory crucible using sodium metal and ferrocyanide.)
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nlegaux
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[*] posted on 12-9-2015 at 16:27


Something else that can be done is a Pictet-Spengler reaction allowing for the creation of interesting heterocycles. All that is required would be the tryptamine, an aldehyde or ketone, and an acid catalyst.

nlegaux
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Noshtuba
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[*] posted on 14-9-2015 at 02:54


careysub do you know of any sources documenting the procedure with mercury cyanide?
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lullu
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[*] posted on 14-9-2015 at 04:42


Reductive amination works with plain NaBH4 when done right.
Also there are a lot of better alternatives to NaBH3CN that are easily prepared and that won't reduce your aldehyde and will work at pH 5.
Have a look at substituted pyridine boranes for example.
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careysub
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[*] posted on 14-9-2015 at 12:07


Quote: Originally posted by Noshtuba  
careysub do you know of any sources documenting the procedure with mercury cyanide?


B. Gyori and G. Emri; J. Chem. Soc., Chem. Commun., 1983, 1303.

Referenced here (pg. 7):
http://cora.ucc.ie/bitstream/handle/10468/1656/MyersM_PhD198...

I do not have the original Gyori and Emri article.
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Cloner
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[*] posted on 15-9-2015 at 07:05


15.1g tryptamine was added to 300 ml shellsol d70 and refluxed with 2.5g spearmint oil. The resulting mixture became beer colored after about 30´. During the operation of the reflux, gas evolved that did precipitate CaOH solution.

However, a wet PH paper held in top of the reflux column did color blue, not red. This is very strange. Could it be NH3? It isn't a good sign at all.

.
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Pumukli
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[*] posted on 15-9-2015 at 11:14


Tryptamine? Wasn't it tryptophane?

(Cloner, your reaction seems to be a decarboxylation attempt. Am I mistaken?)
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Cloner
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[*] posted on 16-9-2015 at 09:05


yes, you are of course right.

I started to wonder if it could be tryptamine itself that is slightly volatile...

[Edited on 16-9-2015 by Cloner]
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