Famousroger
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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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Where are the Peanuts ?
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zed
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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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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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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.
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.
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 .
[Edited on 21-10-2014 by Chemosynthesis]
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Bert
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Thread Moved
21-10-2014 at 09:37 |
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