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Author: Subject: DET from DEET (diethyltryptamine from tryptaphan and DEET)
Famousroger
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sad.gif posted on 16-10-2014 at 20:55
DET from DEET (diethyltryptamine from tryptaphan and DEET)


I was casually eating alone, then it came to me; DET from DEET:

It's simple, really;

Tryptaphan is oxidized by sodium hypochlorite, resulting in the aldehyde (this special reaction of alpha amino acids was well studied in the '30s, one ref here: http://chemistry.mdma.ch/hiveboard/rhodium/pdf/tryptophan.st... )

The resulting aldehyde is then reacted with diethylamine produced by hydrolysis of DEET. I think hydrolysis with sodium hydroxide, resulting in the freebase and the meta-methylbenzoate salt would be apropos if the diethylamine were to be immediately used, otherwise acid hydrolysis to produce the HCl salt of diethylamine would be more practical (but remember kids, you need to produce a good nucleophile for the rxn, so amine salts won't work to form DET). If one thinks about it, this looks quite nice; solvents wise and reagents wise...the only kink is the relatively slow formation of the enamine, that and this process has never been tried.

...and as I write this i continue to be selectively plagued by erratic keyboard behavior reminiscent of an NPR special i had heard regarding illegal NSA surveillance of reporters...we will let the details divulge themselves...again, if there are any nay-Sayers, let them speak!

fRS
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aga
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[*] posted on 19-10-2014 at 15:28


Where are the Peanuts ?



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zed
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[*] posted on 20-10-2014 at 15:28


I read the original papers, 40 or 50 years ago. The oxidation of Tryptophan to Indole-Acetaldehyde, is kinda Sketchy.

Aldehydes of that type, tend to be fairly unstable, if you are able to successfully isolate them in the first place.

Oxidations in general, are difficult to control. And, aldehydes are fragile. So, yeah. This is a possible reaction pathway to Tryptamines. But, in practice, it probably doesn't work very well.

Spend a few weeks mining the Archives. Your knowledge will be enriched.

Also, consult Tihkal. If this oxidation was a winner, Shulgin probably utilized it.

[Edited on 20-10-2014 by zed]
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Haber
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[*] posted on 21-10-2014 at 06:18


Just some thoughts without references:

Tryptophan can be fermented to tryptophol.
Then with tryptophol you can make the tosylate.
The tosylate could then be reacted with the amine of your choice.

Some of the details should be in the old hive archives.

The tryptophol route might be better than the aldehyde one.

[Edited on 21-10-2014 by Haber]
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Chemosynthesis
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[*] posted on 21-10-2014 at 09:10


This isn't really a drug forum. You are probably best off posting your speculations of synthesizing schedule 1 narcotics on a forum dedicated to that kind of chemistry.

Quote: Originally posted by zed  
Aldehydes of that type, tend to be fairly unstable, if you are able to isolate

Not sure what is up with your punctuation, but the aldehyde has a CAS he could look up. Seems as though Shulgin just ordered as professionals do, paperwork and all.

Quote: Originally posted by Haber  
Just some thoughts without references


Hey, why not? Hasn't stopped almost anyone from posting, right? There is a special appeal schedule 1 narcotics have in that all standards in posting fly right out the window nearly whenever they're involved. I mean the thread started out without citing or even explicitly denoting most of the necessary reaction schemes, but I guess now we know why Roger is so interested in getting some OTC borohydride synthesized. I don't even see details about if it's supposed to be one-pot (unbelievable), temperatures, reactions times, purification, or anything.
Very detail lacking for all the worry it's causing the NSA:P.

[Edited on 21-10-2014 by Chemosynthesis]
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Bert
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