Author Topic: DMT from Indole-3-Acetic acid  (Read 1336 times)

Evilblaze

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Re: DMT from Indole-3-Acetic acid
« Reply #20 on: December 12, 2009, 10:34:44 AM »
An other way to indole 3 acetic acid:

Normal indole is an available chemical. At us, it is sold relative cheap (100g/25 euro). From this compound there are a lot of ways to get indole 3 acetic aciid what is the direct precursor of the DMT. Let's see an easy way:

Normal indole with diazoacetic acid ethyl ester in boiling ether gives indole 3 acetic acid ethyl ester. The diazoacetic acid loses the diazo part of the molecule and it just get's on the indole. The formation of the IAA ethyl ester is almost near to 90%. The reaction was described by Jackson in 1935.

The precusors are not hard to get. As I wrote, the indole is available in chem. supply shops. The diazo acetic acid ethyl ester can be made from glycine.

Synthesis of diazo acetic acid ethyl ester:
  from   

The glycine ethyl ester HCl is made by adding glycine to EtOH and bubbling dry HCl gas through it at 65-70 Celsius. The EtOH is also the solvent, so use more that the calculated amount. EtOH slould be added again and again to the reaction, because it will boil out from the mixture. You can get a recipe here: http://www.jbc.org/content/175/2/531.full.pdf
The ethyl ester should be diazotated with NaNO2. This part of the reaction is not so hard. Just cool down the chemicals, get a solvent what dissolves both ot the components (the NaNO2 and the glycine ethyl ester HCl). The glycine ethy ester HCl is soluble in ethanol, methanol, ether, benzne. Maybe the best would be to use methanol as a solvent (sodium-nitrite solubility in methanol: 4.4 g / 100 g 20°C). The diazo acetic acid ethyl ester is a yellow oily liquid. -22 Celsius melting point, boiling point, 140-141 Celsius.

The glycine ethyl ester is soluble in ether so just dissolve it in ether, add the indole to it and start to boil it. After the calculated amount of N2 evolved you are ready with the indole 3 acetic acid ethyl ester. Now you should just add the dimethyl amine to the mixture. And hydrogenate it to get the pure DMT.

-Evilblaze
« Last Edit: December 12, 2009, 10:51:20 AM by Evilblaze »

ausser_betrieb

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Re: DMT from Indole-3-Acetic acid
« Reply #21 on: December 12, 2009, 11:32:58 AM »
thats intresting, it seems doable - the only disadvantage: NaNO2 really doesnt grow on trees and its poisinous - this makes this way less atractive, or is NaNO2 avaivable a way i havent recognized yet?

Evilblaze

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Re: DMT from Indole-3-Acetic acid
« Reply #22 on: December 12, 2009, 12:03:42 PM »
NaNO2 really doesnt grow on trees and its poisinous - this makes this way less atractive, or is NaNO2 avaivable a way i havent recognized yet?

NaNO3 + Pb = NaNO2 + PbO
Just melt these thing together and you are ready.
Or: 2NaNO3 = 2NaNO2 + O2

Or you can buy it in a chem. supply shop. At us it is available and it is cheap, only 8 euro/kilogram. ;D
« Last Edit: December 12, 2009, 12:07:40 PM by Evilblaze »

ausser_betrieb

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Re: DMT from Indole-3-Acetic acid
« Reply #23 on: December 12, 2009, 12:16:21 PM »
well, heating NaNO3 to get it seems doable, so welcome another way to DMT. nice !

timecube

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Re: DMT from Indole-3-Acetic acid
« Reply #24 on: December 12, 2009, 12:57:16 PM »
Thanks, Evilblaze.  I like starting from indole, and still wonder how applicable this reaction is to other primary alcohols:

http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV5P0654#Ref654N1


The reason being that this product is available OTC in bulk powder as its bitartrate salt:

http://en.wikipedia.org/wiki/Dimethylethanolamine


I suppose I need to just go pick up a kilo of indole and stink my house up trying   ;D

shroomedalice

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Re: DMT from Indole-3-Acetic acid
« Reply #25 on: December 12, 2009, 01:14:46 PM »
when you decarboxilate the tryptophane to the aldehyde does the carbonyl condense with the
nitrogen in the indole ?

ausser_betrieb

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Re: DMT from Indole-3-Acetic acid
« Reply #26 on: December 12, 2009, 02:51:12 PM »
timecube, DMT from Indol in one step sounds too good to be true, dosent it? also, for the bees unable to get indole (like me ;_;), get "indol-3-carbinol" and reduce it to indol. Health Supplements - what does one want more?

timecube

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Re: DMT from Indole-3-Acetic acid
« Reply #27 on: December 12, 2009, 03:35:43 PM »
Won't reduction just give you skatole?  I considered oxidation to indole-3-carboxylic acid and then some kind of decarboxylation, but I couldn't find much support for it, and it irks me a bit to pay someone to add the carbinol, then work to remove it again.

shroomedalice, I assume you mean the product of degradation to the acetaldehyde (decarboxylation just gives tryptamine.)  It's not going to spontaneously condense with itself as you need to continually remove the water that forms in the reaction, but when condensing it with dimethylamine you're doing just that and it seems like you could end up with some nasty tar.  I think a large excess of dimethylamine is the only real solution, possibly adding the aldehyde to the amine dropwise.  Dimethylamine has to be kept cold to remain a liquid, though, so the addition and reaction may take a very long time.

ausser_betrieb

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Re: DMT from Indole-3-Acetic acid
« Reply #28 on: December 12, 2009, 04:17:25 PM »
decarboxylisation can be very sketchy, decarboxylation of tryptophan is a good sample, the same catalysator can give 10% or 70% yield depending on the solvent (and vice versa) - so trial and error is not an option (there are too many factor this depends on, if there is an easy procedure with avaivable materials to do this it surely isnt found out by trial and error). maybe bromination and grignard to get a longer tail with an alcohol at the end? and then reductive amination? grignard can be done without working completly anhydrous, but yield will be lower (significantly, i guess) - ref for this is added.

Evilblaze

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Re: DMT from Indole-3-Acetic acid
« Reply #29 on: December 12, 2009, 06:21:41 PM »
The idea with the primary alcohol is really good. My only problem is the 250 Celsius. Anyway it is written that the yield is +80%, but with the stainless steel autoclave and the 18 hour long heating is too hard for me. It is not a synthesis what can you do at home....

Maybe.... With HBr turning the dimethyl-amino-ethanol into dimethyl amino bromoethane? This can be used with the indole to produce DMT and you just need to do a friedel crafts reaction. The only thing is to protect the indole-s nitrogen.


And for my synthesis here is two reference to produce diazo acetic acid ethyl ester from glycine ethyl ester HCl:
http://www.orgsyn.org/orgsyn/prep.asp?prep=cv4p0424
http://www.orgsyn.org/orgsyn/prep.asp?prep=cv3p0392

As soon as I can, I will start the synthesis and I will write down everything in a pdf file.

timecube

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Re: DMT from Indole-3-Acetic acid
« Reply #30 on: December 13, 2009, 12:53:05 AM »
Stainless steel pressure bombs assembled from piping are doable at home, just not the safest things in the world.  The agitation might take a bit of ingenuity.

It should be possible to make the bromoethane into the grignard and add it directly to C-3 without needing to protect the indole nitrogen.

Baba_McKensey

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Re: DMT from Indole-3-Acetic acid
« Reply #31 on: December 13, 2009, 01:33:50 AM »
Someone on the hive said he was experimenting with making DMT from dimethylaminoethanol (dimethylethanolamine) aka DMAE, and indole.  He said he was having trouble getting good yields, but got something that was psychoactive.  Can someone get these two articles?  The second one talks about the reation of indole with ethanolamine and diethylethanolamine. 

Disproportionative Condensations. IV. The 3-Alkylation of Indoles by Primary and Secondary Alcohols
Ernest F. Pratt, Laurence W. Botimer
pp 5248–5250
Publication Date: October 1957
DOI: 10.1021/ja01576a049
http://pubs.acs.org/doi/pdf/10.1021/ja01576a049

Preparation of certain 3-substituted indoles
(Mrs.) Rita H. Cornforth and Sir Robert Robinson,  J. Chem. Soc., 1942, 680
DOI: 10.1039/JR9420000680
http://www.rsc.org/Publishing/Journals/JR/article.asp?doi=JR9420000680
http://www.rsc.org/ejarchive/JR/1942/JR9420000680.pdf

Also see US patents 2407452 and 5037845

http://www.google.com/patents?hl=en


Evilblaze

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Re: DMT from Indole-3-Acetic acid
« Reply #32 on: December 13, 2009, 11:32:49 AM »
Stainless steel pressure bombs assembled from piping are doable at home, just not the safest things in the world. 

It is not the safest thing in the world, you are right.

Why not try to use dimethyl-amino-sodium-ethoxide?(Me2NEtONa) In that case not H2O would come out from the reaction and it would go much easier with much less heat and with a better yield. And to prepare the dimethyl amino sodium ethoxide from the dimethyl amino ethanol is not so hard. Just need some sodium and you are ready.

The only question is the indole-s nitrogen. With the dimethyl amino sodium ethoxide I think the dimethyl-ethyl-amine will go on the nitrogen and not to the 3 position. So: protect it with something, use two times more reagent or make it on by the original method: alcohol + indole + heat :P

timecube

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Re: DMT from Indole-3-Acetic acid
« Reply #33 on: December 13, 2009, 06:21:56 PM »
Thank you for the references Baba_McKensey (and Java, who of course always comes through.)  I have attached them to this post and am reading through them now.

What would be the best way for obtaining the freebase from the DMAE bitartrate salt?  Normally you would basify and extract, but since it's an alcohol, DMAE freebase is soluble in water.  Distillation should work if it doesn't form an azeotrope.  Maybe even salting out would be effective.

I would like to avoid nitrogen protection if possible, since they can be a bit expensive and are something else that has to be ordered from a chem. supplier.

Baba_McKensey

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Re: DMT from Indole-3-Acetic acid
« Reply #34 on: December 14, 2009, 10:33:18 PM »
Thanks, timecube.  Example 1 of US patent 3197479 gives a process for making 3-(2-hydroxyethyl)indole from indole and ethylene glycol.  It looks like you could substitute DMAE free base for the ethylene glycol to get DMT.  You might get better results starting with tryptophan (tryptophan -> tryptamine -> DMT).

quetzalcoatl

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Re: DMT from Indole-3-Acetic acid
« Reply #35 on: December 15, 2009, 02:58:48 AM »
Im trying to keep up with you guys here, but I still feel like im on shakey grounds.

2 Questions:

1) What reaction conditions are necissary for the sodium hypochlorite step? In non-polar solvent, or aqueous?

2) If we are to work this into a useful synthesis, what other reactions are necissary to utilise DMAE instead of reductive amination.
- this would allow for a) a very available precursor and b) reduce the need for excess solvent.

There is a useable and useful reaction in here; and I for one woud like people to know about it because the mass online trade and extraction of mimosa hostillis just seems ethically wrong. Plus, this stuff will be crystal-clean. :D

timecube

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Re: DMT from Indole-3-Acetic acid
« Reply #36 on: December 18, 2009, 07:53:54 AM »
1) It's just a strecker degradation, which is fairly well documented.  There's a whole thread on it in the references section, and it's covered at Rhodium's archive as well.

The condensation between indole-3-acetaldehyde and dimethylamine followed by reduction, is analogous to the condensation between MDP2P and methylamine followed by reduction during the production of MDMA, except instead of an imine, an enamine is being formed, which is a bit more reluctant to form, so active water extraction via a dean-stark type of setup or a drying agent may be necessary.  A solution of the aldehyde in say MeOH should probably be added dropwise to dimethylamine HCl in MeOH with good stirring, and water continually removed via some means to push the equilibrium the toward the enamine.   I'm not sure how much heat if any would be needed, or if it could be directly reduced as it forms like with the MDMA prep.  You'd have to play around with it some.

2) Like I said, the DMAE freebase could be extracted from the OTC bitartrate salt with a NaOH solution, then separation of the alcohol potentially via a simple salting out.

Then it would need dried and used as in the references provided above.

quetzalcoatl

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Re: DMT from Indole-3-Acetic acid
« Reply #37 on: December 22, 2009, 03:12:07 PM »
@Evilblaze: What do you know about making that ether from IAA? because you can buy IAA straight OTC - or is that what you allready posted? because it seemed overly complex and involving buying from chem stores (not something I want to ever do, ever.)

quetzalcoatl

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Re: DMT from Indole-3-Acetic acid
« Reply #38 on: December 22, 2009, 03:14:18 PM »
Also, thanks Timecube. Im getting my head around this, but Its still a bit off a workable tek.

Evilblaze

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Re: DMT from Indole-3-Acetic acid
« Reply #39 on: December 22, 2009, 09:11:59 PM »
@Evilblaze: What do you know about making that ether from IAA? because you can buy IAA straight OTC - or is that what you allready posted? because it seemed overly complex and involving buying from chem stores (not something I want to ever do, ever.)

What ether do you talk about? The only ether what was mentioned in this topic was the diethyl ether what is used as a solvent.

Or you mean under ether the IAA ester? The methyl ester what is used to make DMT? The ester is made easily. Just dissolve the IAA in excess of MeOH, add 2% of cc. H2SO4 and boil it. You will get a crystalline solid the IAA-methyl ester (and don't forget to get out the H2SO4 with CaCO3!).

Or what do you mean under ether? I just don't know it. Sorry.