forgotten - 11-10-2007 at 20:12
A few years ago there was discussion in regards to synthesis of 3 dimethylamino indole from a starting reagent 3, indole acetic acid
It has been a while, and this post is merely to see if anyone can confirm this hypothetical sequence of events, accurate.
Indole -> 3-acetyl indole -> 3 bromoacetyl indole -> 3 dimethylamino indole -> dimethyl tryptamine
(please forgive me if these compounds are not named correctly, infact, the main reason for this post is to get some sort of confirmation that this is
the theoretical synthesis)
The end product in theory could be reduced with NaBH4, instead of the more well known and dangerous methods requiring LAH or cyano-borohydride..
The use of NaBH4 is what made this hypothetical synthesis stand out quite some time ago. I can vaguely remember details. My brain has this habbit of
making room for new information. If only I had saved the details on actuall paper!! Once the site I used went down, so did this synthesis..
Lego, Manichi, my friend who eats the belgium waffles wearing a gas mask in his attic/lab?
much appreciated =D
forgotten - 11-10-2007 at 20:17
Another note.. and of great importance.. The reduction utilizing NaBH4, of 3, dimethylamino indole -> dimethyltryptamine HAD to take place in a
specific alcohol.. n-propyl alcohol.
ring any bells?
Why is there no litterature on this? So wo isn't me went through a lot of work to provide a full photo essay with all details and it was never
published.. if I am wrong, and I surely hope I am, then please enlighten me.
Sauron - 11-10-2007 at 20:28
DMT is not 3-dimethylaminoindole. It is Dimethylaminoethylindole.
Tryptamine is 3-(2-aminoethyl)indole
Was that helpful?
DETRITUS
[Edited on 12-10-2007 by Sauron]
forgotten - 11-10-2007 at 20:30
3, dimethylamino indole is the precursor to DMT in the above text.
Sauron - 11-10-2007 at 21:37
Nope
If that's what the "text" says then the text is not worth the paper it is written on.
Let's assume Ind = indole
3-Ind-CH2-COOH -> 3-Ind-CH2-COBr -> 3-Ind-CH2-CONMe2 ->
3-Ind-CH2-CH2-NMe2 the last step being the reduction of amide to amine usually done with LAH.
Problem typical of NaBH4 is poor solubility also I don't know why you think sodium cyanoborohydride is dangerous. It is MORE selective than NaBH4.
LAH is not particularly hazardous in competent hands. In less than competent hands MANY things are hazardpus.
3-dimethylindole is 3-Ind-NMe2. How would you explain the disappearance of the two intervening carbons? That is no reduction. That is a stupid
mistake. Will not happen and the claimed product is not DMT nor a precursor of DMT.
forgotten - 11-10-2007 at 22:04
NaBH4 is just more readily available than cyano or LAH and thats why the promise of this reaction scheme was very anticipated. The only downside was
the yeild, which was very low, if I recall, 30-40%.
Please help me here, how would you hypothetically propose a synthesis from what I have provided? As I said, this is a few years ago, and details are
very fuzzy, but I can assure you 100% the end result was dynamite. Too much time has passed and too much new knowledge has overcome me in my studies
for me to remember much more.
However, after the bromination, the compound recovered then is reacted with aq. dimethylamine to what I thinkkkk produced 3, dimethylamino indole
This was then reduced using NaBH4 in n-propyl alcohol to DMT (in pretty low yields) but after workup and chomatography the results were very much
worth the work.
Sorry I can not remember much more. I never thought "that" site would have gone offline.. it did so a few weeks after the details of this route were
posted
ah well, maybe someone will read this and remember what I am speaking of. Not many people were contributing to this back then as it was purely
theoretical until actually carried out. The light is green..
[Edited on 11-10-2007 by forgotten]
forgotten - 11-10-2007 at 22:13
yes, you are right! You do make the amine! I think that takes place after the reduction using NaBH4.. I rememeber rhod explaining this to me. I was
confused as to the nomenclature when reffering to these compounds. Does this make a little more sense now?
I am certainly not a chemist, I am only in my 2nd year of chemistry classes, currently taking Organic and Clinical Med Labs, so go easy on me, I am
just trying to get the correct sequence using the proper nomenclature.
Thanks for your patience =)
[Edited on 11-10-2007 by forgotten]
[Edited on 11-10-2007 by forgotten]
Sauron - 11-10-2007 at 23:55
BTW indole-3-acetic acid is easily made in an autoclave (pressure reactor) from indole, aqueous glycollic acid and KOH at 250 C for 18 hours with
shaking or stirring (it's not a vodka martini!) in 90% yield on a half a Kg yield basis. Biggest problem is where to get 350 g indole to start with.
See Org.Syn. Glycollic acid is hydrocyacetic acid.
It is a natural plant auxin and is used as a control in plant growth research, so if you are a phytochemist or a botanist maybe you can buy some but I
don't think you will find it down at the seed store.
Indole can be synthesized somewhat tediously from o-toluidine, but damn, the DEA watches that too, because of its use in making methaqualone. I
suppose you could buy o-nitrotoluene or even nitrate toluene and seperate the isomers. It's the oily liquid one. Then reduce it to o-toluidine with
tin and HCl. The indole prep is a bit of a pain and indole smells EXACTLY like shit only more so and very intensely and persistently. Its N-methyl
derivative is even named for shit (skatole). If you can succeed in making indole without making yourself and your lab smell more or less permanently
like an outhouse you will get a certificate as a good chemist.
[Edited on 12-10-2007 by Sauron]
Attachment: CV5P0654.pdf (140kB)
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Nicodem - 12-10-2007 at 00:10
Glycolic acid is used in the Org. Synth. method and not acetic acid.
Forgotten, your posts and questions make little sense. If you don't know how to use chemical nomenclature then draw the structures and reactions you
are asking about. It also helps if you post in correct forum sections and avoid talking about off topic stuff. Searching before posting also helps (if
you know how to UTFSE correctly).
Sauron - 12-10-2007 at 01:10
brother Nicodem, this young man would not gave gotten very far if he UTFSE for 3-dimethylaminoindole, now, would he?
anyway TFSE sometimes JDFW, which stands for Just Doesn't Fucking Work. All too often in fact. Its performance is at best spotty. Posts on this forum
show up faster in Google than in our own beloved FSE.
Maya - 12-10-2007 at 05:21
yep, TFSE is WS ( worth sh$t ) on this board, doesn't work.......
use another search engine instead
If you use google type in what you are trying to find and also "www.sciencemadness.org" in parenthesis and google will search that particular website
for you
forgotten - 12-10-2007 at 06:13
googling 3, dimethyaminoindole did no goood as Sauron said. This was this all was clarified to me. Nomenclature and the process of the amide forming
the amine was not clearly stated in my posts. The amide is not soluble in H2O as this is remembered when vacuum filteration was performed after the
bromo compound was treated with aq. dimethyamine. (dimethylamine gas dissolved in water). When added to n-propyl alcohol the amide went into solution
at which point the NaBH4 was added for amination to dimethyltryptamine.
It 100% certifiably mind blowingly worked, just wasn't clear exactly the correct sequence of events that would be only properly described by a
chemist. Once again, thank you Sauron.
Now, off to ace major exam.
-ciao
Maya - 12-10-2007 at 07:19
<<< googling 3, dimethyaminoindole did no goood as Sauron said >>>
Well if you start with cr@p, you end up with cr@p. simple as that. You have to tweak the search engine for correct and very precise terms, sometimes
many times in many different combinations . a search engine is no mind reader
Polverone - 12-10-2007 at 09:35
I think I'm going to close this one before it completely flies off the rails. Nicodem's suggestion about drawing structures is very good to keep in
mind for the future. Chemical names can be confusing and variable but a drawing tells all.