DMT from gamma-aminobutyric acid

[farukhocaoglu]

I've always wanted to make DMT but couldn't do it from OTC chemicals and all the syntheses I found needed NaBH4 or other derivatives of it. Then the Fischer Indole synthesis came to mind, but I couldn't find any recipes here, or the ones I found started with 4-chlorobutanal, which I didn't have access to either. That's why I came up with this synthesis here from gamma-aminobutyric acid which is used as a rooting hormone for plants.

Is this recipe plausible at all? If not, is there a way to modify it in a way that it can be done with OTC chemicals or is there a known recipe for 4-(N,N-dimethylamino) butanal diethyl acetal that can be made from OTC chemicals?

 

[Joker_55555]

I've always wanted to make DMT but couldn't do it from OTC chemicals and all the syntheses I found needed NaBH4 or other derivatives of it. Then the Fischer Indole synthesis came to mind, but I couldn't find any recipes here, or the ones I found started with 4-chlorobutanal, which I didn't have access to either. That's why I came up with this synthesis here from gamma-aminobutyric acid which is used as a rooting hormone for plants.

View attachment 10334

Is this recipe plausible at all? If not, is there a way to modify it in a way that it can be done with OTC chemicals or is there a known recipe for 4-(N,N-dimethylamino) butanal diethyl acetal that can be made from OTC chemicals?

farukhocaoglu

Hi

In the second step, the ester cannot react with trimethoxymethane, even if it does, one carbon is added to the chain and the chain has 5 carbons.

 

[Joker_55555]

I designed such a method, it may be successful, but it is not cost-effective

 

[farukhocaoglu]

I don't have LiAlH4, PCC or TsCl. I've been working hard to get an OTC-friendly recipe but I guess making DMT from OTC chemicals is impossible unlike amphetamines.

 

[Joker_55555]

I don't have LiAlH4, PCC or TsCl. I've been working hard to get an OTC-friendly recipe but I guess making DMT from OTC chemicals is impossible unlike amphetamines.

farukhocaogluYes, indole-based compounds are expensive and difficult to synthesize even by conventional methods.

 

[farukhocaoglu]

Yes, indole-based compounds are expensive and difficult to synthesize even by conventional methods.

Joker_333I'm also assuming there isn't any way to make 4-chloro-1-butanol in an amateur lab without using THF.

 

[Joker_55555]

I'm also assuming there isn't any way to make 4-chloro-1-butanol in an amateur lab without using THF.

farukhocaogluThe most convenient way is the synthesis of 4-chloro-1-butanol from THF. Even if you don't have a vacuum pump, you can easily make one.
You can almost make it at 50-55% concentration.

 

[summer_child]

The addition of HCl to the double bond is strange, i found a reference for it (here), but I guess it could be replaced with HBr and a peroxide since it is a better known addition that would make the anti-Markovnikov product.

 

[Joker_55555]

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The addition of HCl to the double bond is strange, i found a reference for it (here), but I guess it could be replaced with HBr and a peroxide since it is a better known addition that would make the anti-Markovnikov product.

summer_childHello, in the second step, as you said, hcl cannot be added as an anti-Markonioff reaction, the anti-Markonioff reaction must continue. In the last step, such a reaction does not take place because the carbon is protected by 3 Oxygen. Trimethoxy methane can react under acidic but not basic conditions.

 

[summer_child]

Hello, in the second step, as you said, hcl cannot be added as an anti-Markonioff reaction, the anti-Markonioff reaction must continue. In the last step, such a reaction does not take place because the carbon is protected by 3 Oxygen. Trimethoxy methane can react under acidic but not basic conditions.

Joker_333The grignard with trimethyl orthoformate? It's a known reaction - Bodroux–Chichibabin aldehyde synthesis

 

[Joker_55555]

The grignard with trimethyl orthoformate? It's a known reaction - Bodroux–Chichibabin aldehyde synthesis

summer_childThat's right, I just saw Bodroux–Chichibabin Also, in step 2, the intramolecular reaction also occurs.

 

[summer_child]

That's right, I just saw Bodroux–Chichibabin Also, in step 2, the intramolecular reaction also occurs.

Joker_333This paper also states that the anti-markovnikov addition of HCl is possible if it is bubbled into molten N,N-dimethyl allylammoniun chloride

 

[Joker_55555]

This paper also states that the anti-markovnikov addition of HCl is possible if it is bubbled into molten N,N-dimethyl allylammoniun chloride

summer_childAt high temperature, the reaction is likely to proceed as a radical. These reactions are difficult to perform in home laboratories, these are mainly industrial methods.

 

[MikeBlast]

5-HO-aMT from acetaminophen

1. Photolysis of acetaminophen https://link.springer.com/article/10.1039/c2pp25341k
2. Alpha keto chlorination https://sci-hub.se/10.1080/00397910500334637
3. Indoline formation
4. Aldol condensation with acetone
5. Reductive amination

(1) can also be used to make 2-amino substituted phenylethylamines

 

[Opal]

Is everyone in this thread mad? You are not going to fuck around with aluminium amalgams, HCl gas, Grignards, phenylhydrazine and so on and then say that NaBH4 is out of the question. If you want tryptamines, you do reductive amination on tryptamine with NaBH4 or whatever else, or the Shulgin route with indole and oxalyl chloride — not this. This is just insanity and shows that none of you have been doing this for more than a few months at most.

 

[Sue]

or you could extract from plants and be done with it.
All over the counter...