Sciencemadness Discussion Board - Indole-3-carbinol into dmt

Indole-3-carbinol into dmt

cheddafries - 5-12-2013 at 11:35

So I'm new to the chemistry community and this forum, but I have a good knowledge of chemistry and organic chemistry. After doing some research, I found a possible two step reaction to turn I-3-C or C9H9NO into DMT or C12H16N2. First it would start out with I-3-C, Methyl Alcohol (CH4O), and Sulfuric Acid (H2SO4) into I-3-COC (C10H11O). Then adding Dimethylamine (C2H7N) to I-3-COC would result in DMT. I'm not sure if this is plausible or not or how exactly I would go about this. Any suggestions or feed-back would be awesome.

This is for theoretical purposes only.

Random - 5-12-2013 at 11:39

Strong first post

cheddafries - 5-12-2013 at 11:52

thanks. I've had this idea in my head for the longest time and I finally think this is the way. I've read quiet a few other forums and many enteries in TiHKaL and I'm hoping I'm not too far off. its just two substitution reactions; replacing the alcohol with a dimethyl ether I believe, and then replacing that with an amine. I'm just not sure on heating, temps, pressures, energy and stuff like that. I don't know too much about Indole (I've been trying to find a chemistry book on it), but if I just focused on the chain itself neglecting the beneze and pentane rings, it would just be turning ethyl alcohol into ethoxymethane. Then turning that into propylamine. Correct?

Nicodem - 5-12-2013 at 11:58

Quote: Originally posted by cheddafries

thanks.

He was being sarcastic, or he would better be.

cheddafries - 5-12-2013 at 12:10

of course! I'm just one of those people its hard to tell if I'm being sarcastic or not and sorry for the triple post I'm new here and it said it didn't go threw.

Nicodem - 5-12-2013 at 13:29

Quote: Originally posted by cheddafries

of course! I'm just one of those people its hard to tell if I'm being sarcastic or not and sorry for the triple post I'm new here and it said it didn't go threw.

I said "he", not "you".

Anyway, what references do you have for the reactions you talk about? They make no sense whatsoever to me. The first one is unlikely to happen, at least not in the presence of sulfuric acid. You might get the ether by heating indol-3-ylmethanol in methanol in a presence of a strong base (NaOMe or NaOH). The base catalysed elimination/addition is a viable mechanism for this substrate, but I can't see how this reaction would proceed under strongly acidic conditions without going in undesired directions. But at least this might be possible under properly designed conditions (a literature search would answer you that), while the next step makes no sense whatsoever. Not only is there no viable mechanism, you also call for magic intervention as you create a -CH₂- out of nothing.

If you triple-post by mistake, you can use the "Edit" button to delete the superfluous posts. And make sure you read the forum guidelines. For the beginning, start posting in the correct forum sections and stop using self-made acronyms (they make you appear either clueless or mocking on science, neither is good).

Pyro - 5-12-2013 at 13:32

@Nicodem:shoudln't this belong on organic chemistry or whimsy (to keep it off the radar)

Nicodem - 5-12-2013 at 13:36

Quote: Originally posted by Pyro

@Nicodem:shoudln't this belong on organic chemistry or whimsy (to keep it off the radar)

Beginner topics belong to the Beginner's forum section (hence the name). What radar are you talking about? Radars can only detect objects that reflect microwaves. As far as I know internet forums, or any other virtual reality creations, can't be considered true objects, and even if they would be, I'm quite sure they do not reflect microwaves.

Pyro - 5-12-2013 at 13:42

Haha Nicodem, you know what radar I mean

,
a thread discussing the preparation of DMT isn't exactly the thing we want everybody seeing here

Nicodem - 5-12-2013 at 14:01

Quote: Originally posted by Pyro

Haha Nicodem, you know what radar I mean

I'm not sure I do. Does this have something to do with those paranoid crackpots that envelop their heads in tin foil? Tin foil does reflect microwaves, but I'm not very familiar with their reason (or lack thereof), so I'm not competent enough to understand what you mean.

Quote:

a thread discussing the preparation of DMT isn't exactly the thing we want everybody seeing here

What makes you think so? I would not mind to see scientific discussions about such a compound on this forum, but I don't like threads that start without any reference (like this one) or those that demonstrate nothing but mental masturbation based on wishful thinking rather than science (like ...). Just in case you haven't noticed it yet, not only does this forum tolerate scientific discussions about psychoactive drugs, we even have a section especially dedicated to the scientific discussion of energetic materials. We are so nice.

NexusDNA - 5-12-2013 at 14:06

I think this has been discussed before.

http://www.sciencemadness.org/talk/viewthread.php?tid=9653#p...

Pyro - 5-12-2013 at 14:30

I meant the radar that you can stay off of by not asking questions such as ''how do I make meth?''

I see your point. you are correct.

cheddafries - 5-12-2013 at 19:57

Quote: Originally posted by Nicodem

Quote: Originally posted by cheddafries

of course! I'm just one of those people its hard to tell if I'm being sarcastic or not and sorry for the triple post I'm new here and it said it didn't go threw.

Oh sorry I'm pretty poor in English, and I'm not trying to mock and maybe I am a little clueless. I didn't know how to abbreviate.

As for my reference I got it from
http://www.erowid.org/archive/rhodium/chemistry/indoleacetic...

I figures since the structures were close the mechanisms and reactants would be the same. The second part I would think have the carbon-oxygen-carbon bond break off leaving a negative charge and would attach to the longer chain of Dimethylamine. I'm guessing it would go under similar conditions as the first reaction.

I don't mean to be a jack-ass and clueless. I don't know where else or who else to discuss this with.

cheddafries - 5-12-2013 at 20:06

Also would it be wrong of my to go about this reaction by neglecting the indole group and trying to figure out a way by just focusing on the chain? Or would I just look more clueless?

violet sin - 5-12-2013 at 23:38

t-shirt spam reported.

turd - 6-12-2013 at 01:47

Quote: Originally posted by Pyro

a thread discussing the preparation of DMT isn't exactly the thing we want everybody seeing here

Who is "we"? I got very positive responses to this thread: https://www.sciencemadness.org/whisper/viewthread.php?tid=23... thus it seems that some people are interested in this kind of chemistry.

And why not? DMT is a fascinating material, the chemistry of tryptamines is fun [completely different from phenethylamines] and amateur friendly since tryptophan is so widely available.

I hope for you that your hubris is age-related.

Quote:

Also would it be wrong of my to go about this reaction by neglecting the indole group and trying to figure out a way by just focusing on the chain?

No - tryptamines tend to be quite unstable and cyclize under certain conditions (https://en.wikipedia.org/wiki/Pictet%E2%80%93Spengler_reacti...) that would be all right with phenethylamines - you cannot ignore the rest of the molecule.

Pyro - 6-12-2013 at 02:46

Yes, there is no reason not to discuss it, but DMT is a schedule I substance in the US.
I am merely stating a fact, home chemistry is already difficult because of cooks.

by ''we'' I mean home chemists

turd - 6-12-2013 at 04:22

As a "home chemist" I ask you not to use the word "we" since you do not speak in my name. Moreover, I have to note a certain level of hypocrisy since AFAIK the latest round of proposed regulations (HNO3, H2O2) are due to the perceived threat of people blowing their fingers off.

In short: you are barking up the wrong tree. The problem is not people cooking DMT, the problem is DMT being regulated. Regulation is silly for other psychoactives but absurdly ridiculous in this case.

Nicodem - 6-12-2013 at 08:16

Quote: Originally posted by cheddafries

As for my reference I got it from
http://www.erowid.org/archive/rhodium/chemistry/indoleacetic...

There in nothing in those two articles that resembles what you talk about in your first post above.

Quote:

I figures since the structures were close the mechanisms and reactants would be the same.

First of all you need to understand that the reaction mechanisms are not related to the the aesthetic aspects of the structure drawing, but to the actual molecular structures as such. A molecular structure is about the connectivity between the atoms. It is this bonding that defines the possible reactivity and viable reaction mechanisms: which bond can break and form under the given reaction conditions. For this reason, wishfull thinking can not affect the reaction outcome. Consequently, only science could ever create the knowledge needed to predict a chemical reaction outcome with at least some relevant confidence.
My advice to you is to stick to the scientific method, if you ever want to learn anything about organic synthesis. It's an art that needs discipline. Try first by reading some basic chemistry textbooks. Leave aside the scientific articles for later, as you obviously do not yet understand them - they will only confuse you further until you have the necessary knowledge base and methodology to comprehend. Once you are done with school textbooks, after 2 or 3 years and a few dozens of textbooks, go for scientific books and review articles, and obviously, if you are ever to do any synthesis, you also need to read about the synthetic techniques.

Quote:

The second part I would think have the carbon-oxygen-carbon bond break off leaving a negative charge and would attach to the longer chain of Dimethylamine. I'm guessing it would go under similar conditions as the first reaction.

Just to give you an example, here you talk like you want things to go the way you wish, even though what you say makes no sense whatsoever in a scientific sense. Atoms cannot be created out of nothing and bonds cannot form unless there is a possibility of electrons participating in the bond formation. For example, nucleophiles cannot react with nucleophiles, when both participate in the reaction only as nucleophiles.

zed - 6-12-2013 at 16:25

That side chain looks to me to be a carbon atom short. Also, the indole ring, might not be stable to the presence of a strong acid like H2SO4. Finally, I know of no such reaction.

There is however a method of converting Indole-3-ethyl carbinols (Tryptophols) into tryptamines.

Somewhere, I have a paper on the subject. The process was developed to produce Sumatriptan type products.

[Edited on 7-12-2013 by zed]

[Edited on 7-12-2013 by zed]