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just a thought

Migrated topic.
As for the potentiating effects of ULM-491 on DMT I could only speculate.

Does anyone know of any other studies involving the pharmacological interactions between other lysergamides and DMT?

there's a compound called lisuride (systematic (iupac) name:1,1-Diethyl-3-(7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinolin-9-yl)-urea) which is a lysergamide antiparkisons agent, and is also used in the treatment of migraines, any way this compound has a very similar pharmocological profile to ULM-491, and I would be willing to bet that lisuride would also have potentiating effects when used as a primer to N,N-Dimethyltryptamine.

-EG
 
Mindlusion said:
Well, the nitrogen on the tail end is a tertiary amine. Its not going to react with anything that is going to force the triazole to leave. All you are doing is making the nitrogen on the triazole take back its electrons, not reacting anything with it directly.

Again, I don't know how easily you could remove it where it is located, probably not easily at all. If it was on the indole directly, you could do a nucleophillic aromatic substitution.

It is pretty difficult to work backwards from a single molecule, retro-synthesis is an important technique to solve problems in organic synthesis, but it involves working backwards from the final product, in this case DMT. Its difficult to work backwards from a reactant like you are trying to do here.
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Hold on: wouldn't anything that forced the triazole group to leave also remove the amine from the tail, leaving you with something like 3-ethylindole?

Blessings
~ND
 
Nathanial.Dread said:
Mindlusion said:
Well, the nitrogen on the tail end is a tertiary amine. Its not going to react with anything that is going to force the triazole to leave. All you are doing is making the nitrogen on the triazole take back its electrons, not reacting anything with it directly.

Again, I don't know how easily you could remove it where it is located, probably not easily at all. If it was on the indole directly, you could do a nucleophillic aromatic substitution.

It is pretty difficult to work backwards from a single molecule, retro-synthesis is an important technique to solve problems in organic synthesis, but it involves working backwards from the final product, in this case DMT. Its difficult to work backwards from a reactant like you are trying to do here.
Click to expand...
Hold on: wouldn't anything that forced the triazole group to leave also remove the amine from the tail, leaving you with something like 3-ethylindole?

Blessings
~ND
Click to expand...
Not necessarily; dimethylamine is less good a leaving group than 1,2,4-triazole, as Mindlusion more or less implied at the start of their post. But I think it might be fairly tricky to get the reaction conditions right to get the triazole off without wrecking the rest of the molecule.

To what extent does an indolmethyl group resemble a benzyl group? Benzyl is quite easily removed with catalytic hydrogenation.
 

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downwardsfromzero said:
Not necessarily; dimethylamine is less good a leaving group than 1,2,4-triazole, as Mindlusion more or less implied at the start of their post. But I think it might be fairly tricky to get the reaction conditions right to get the triazole off without wrecking the rest of the molecule.

To what extent does an indolmethyl group resemble a benzyl group? Benzyl is quite easily removed with catalytic hydrogenation.
Click to expand...

Actually, indole is even more electron rich than benzene. It is even better at stabilizing it's benzyllic hydrogen on the methyl group. You can draw a lot of resonance structures to stabilize the negative charge of the 4 position methyl. So it may actually be easier than one would initially think, but you would still be suck with 4-methyl-DMT.

A catalytic hydrogenation would work by breaking the bond between the 4-methyl and the triazole, due to the resonance stability of the benzyl (indole) as well as the resonance stability of the triazole hetero-cycle, the bond is weak enough in a sense, to be treated like a pi bond and hydrogenated. Cool!

--

Although, this reaction might not work with indole, we are assuming that the charge can be stabilized along the benzene ring. The indole 2 and 3 carbons are strongly nucleophillic. These carbons are key in the pictect-spengler and fischer indole. Since C2 is not yet substituted, the resonance forms of the benzene ring might not work the way we would like them to. Perhaps until this carbon is also substituted, such as in a beta-carboline, then you could have a stable benzylic anion to hydrogenate.
 
Ah, but with Rizatriptan it'd be a 5-methyl. I'll have a go at drawing out the resonance forms for the indole equivalent benzylic um, thingy.

But as mentioned, being stuck with 5-methyl DMT wouldn't necessarily be a problem.

Edit: looking at it, benzylic cations would be more stabilized in 5-methylindole derivatives than the corresponding anions. This is due to the electron-rich pyrrole portion of the molecule as you said.
 
My mistake, it is 5-methyl.

Also remember if it is a hydrogenation we are looking at, we would be dealing with a benzyl anion, not a cation.

Again like I said, indole is a bit of a special case. It will not undergo EAS on its benzene moiety of the ring unless the c2 and c3 of the pyrrole moiety have been substituted. I am not sure how this may play out in stabilizing the benzyl anion, though. But, with the methyl group already there on the 5 position, I cannot see how it could affect it through resonance. I think this reaction is very possible, worth a try.
 
downwardsfromzero said:
From what I gather, it looks like it'd come apart nicely with the appropriate catalyst and homogeneous hydrogen source.
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I think we're all forgetting that dimethylamine is a watched, hazardous reagent.
 
1ce said:
downwardsfromzero said:
From what I gather, it looks like it'd come apart nicely with the appropriate catalyst and homogeneous hydrogen source.
Click to expand...


I think we're all forgetting that dimethylamine is a watched, hazardous reagent.
Click to expand...

There will be no free dimethylamine, this question was asked earlier in the thread. The amine tail is saturated and aliphatic, you might get 1 molecule of diethylamine every 10 million years or something, but the electronics for that reaction just aren't there. In the case of the triazole, it is pretty cool because you have two sets of intramolecular electronics going on at the same time which could push the reaction to completion. Wilkinson's catalyst could work.
 

The link above is:
Tungstate-Catalyzed Oxidation of Triptans with Hydrogen Peroxide: A Novel Method for the Synthesis of N,N-Dimethyltryptamine N-Oxides

Author: Purna Chandra Ray; Vasantha Mittapelli; Yogendra Kumar Chauhan; Babu Rao Konudula;Om Dutt Tyagi

Journal: ChemInform

Year: 2009

DMT N-Oxide to Freebase DMT - DMT-Nexus Wiki

wiki.dmt-nexus.me wiki.dmt-nexus.me
The wiki above is for converting DMT-n-oxides into freebase DMT

-EG
 
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