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Author: Subject: 5MeO - DMT
Ephoton
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[*] posted on 6-7-2008 at 02:57
5MeO - DMT


I think as things are getting a bit relaxed here I can talk about this already naturaly available substance with
a theoretical stance ;P.

My thoughts on its synthesis are that one could start from
readily available melatonin with a simple hydrolisis like
was posted by KMnO4 15 percent HCl refluxed should give
the 5MeO tryptamine as the HCl salt and acetic acid.

now comes the fun part and the part I would like to discuss.

If one is to look into rhodiums archive one will find that most
people have opted for an imine formation with formaldehyde
then the reduction of formed imine with sodium cyanoborohydride.

This to me is way out of the question. The substance alone
is near impossible to get and I realy do not wish to
track Sodium borohydride down then react if with sodium
cyanide.

my thoughts on a possible alternative is of course the good
old Al amalgum. The reason I think this should work
is it works for ketone imine reducts with out effecting
other functional groups in phenethyl amine chemistry.

the hint that this will work with secondary amines was
for me the problem of the dimethyl amine in the old P2P
cooks and MDP2P cooks threads on the hive.

it seamed that they were able to (even if unwanted)
form the dimethyl phenethylamines due to dimethyl amine
impurities in there hexamine hydrolisis.

so in a nut shell I belive it is possible to make a reasonably long lived (compared to DMT) indole in
two steps from something that is very easily and OTC
available.

on a side note I have been informed that this substance
is a lot kinder to the traveler than conventional DMT as well.

If this post is out of the sites guides for interesting and
correct posting then please either delete it or modify it.

otherwise if anyone has any comments or ideas please let
me know :).

[Edited on 6-7-2008 by Ephoton]




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Sauron
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[*] posted on 6-7-2008 at 05:48


I believe in my Melatonin thread you proposed this and Nicodem explained to you why it won't work.

If you want to end up with the dialkyl tryptamine you are better off building it into the synthesis from the start rather than trying to shortcut via melatonin.

In that thread at least one literature reference was cited for a 5-Meo-substituted product's preparation that was quite specifically to produce the N,N-dimethyl product.

My advice is reread that thread and pick up the trail. What you have in mind above is a waste of melatonin.




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sonogashira
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[*] posted on 6-7-2008 at 11:08


Hi Ephoton!
You could try alkylating with MeI to the quaternary salt then demethylating with DABCO in DMF (See attached paper - Very kindly provided by a member of this forum some time ago).

Best of Luck!

I can't find the discussion to which you refer in the melatonin thread sauron, perhaps it has been deleted/edited? Who knows? Sounds like an interesting suggestion to use Al/Hg but what do I know?!)

Edit: I recall reading in I think it was March 6th Edn that Ethanolamine can be used to demethylate quaternary salts, might be worth looking up the reference if you're interested.

[Edited on 6-7-2008 by sonogashira]

[Edited on 6-7-2008 by sonogashira]

Attachment: Demethylation with DABCO-DMF.pdf (828kB)
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[*] posted on 6-7-2008 at 17:44


No that thread has not been deleted. The FSE found it right away.

http://www.sciencemadness.org/talk/viewthread.php?tid=10120&...

See Nicodem's post there critiquing ephoton;s suggestion to deacetylate melatonin as a route to 5-MeO-DMT.




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Nicodem
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[*] posted on 7-7-2008 at 08:50


My reply in that thread was not to Ephoton, but to Hempshaman who asked if the acetyl group could be replaced with two methyls and I explained him that is not possible without first removing the N-acetyl and gave him a literature example of melatonin hydrolysis to yield 5-methoxytryptamine.

Reductive amination of 5-methoxytryptamine could perhaps be performed with sodium triacetoxyborohydride (STAB) using paraformaldehyde. STAB does reduce aldehydes but it reduces the imines much faster and since HCHO makes pretty stable imines and relatively rapidly it is quite possible such methylation could actually work.
The reductive amination using aluminium amalgam is problematic as it involves a lot of heat and works better with slightly acidic media (heat and acidic media are incompatible for tryptamines in the presence of formaldehyde). If modified to run at room temperature and bellow, with conc. aqueous formaldehyde at neutral media then it could perhaps work.




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Ephoton
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[*] posted on 18-7-2008 at 00:16


Nicodem you are truly amazing :).

So I was on the right track by the looks of it.

only replacing the acid hydrolisis with a base hydrolisis.

STAB goes back to NaBH4 anyway so its probably easier to make the cyanoborohydride instead.

I still think the amalgum might be talked into working with the imine formed from a tryptamine
and formaldehyde.

maby if one was to do the imine formation of a single N methyl group then did the reduction
at lowish temps.

repeated the who process again to add the second N methyl group.

im still a little new in indole chem :(.




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