Author Topic: novel newbee tryp decarb question session  (Read 5723 times)

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  • Guest
novel newbee tryp decarb question session
« on: May 18, 2004, 03:08:00 AM »
This was passed on to me

“Tell me what cha think,

In a microwave reflux situation, tryptophan (about 7g) is refluxed in glycerin (about 125 mL) with a small amount of enone (pugelone) until no more gas comes out top of condenser, takes a few minuets for this to happen. As solution is heated, tryptophan appears to dissolve and solution begins to take on a dark reddish brown color. As this occurs there is the definite smell of something “DMT-ish” Solution is cooled, it is a deep dark rust color.

Solution is around ph 7.4 or 7.8 (author can’t remember what was told) Solution is then basified with saturated NaOH solution, pH is 11.5. What looks like some whitish-yellow substance has come out of solution. Solution is diluted with a small amount of H2o and thrown in to sep funnel. An amount of chloroform is added and sinks to bottom. Sep gets well shaken. The result is a clump of red-brown stuff floating about with the rest of solution now a lighter color of rusty orange-yellow. At the bottom of sep is a small amount of chloroform, noticeably less than what was originally put in, it is a rusty orangey color.

A small amount of the sticky brown stuff is taken out and subject to muritic acid and then boiling chloroform, both seem to have no effect on the substance (it does slightly color the chloroform yellow).

Should be noted that the individual has smelled free-base DMT but no other indole before (except tryptophan) The size of the brown lump is about the same size as the original amount of tryptophan.

Is glycerin a suitable for this?

Is this appropriate reasoning?>If one has an amine in an alcohol, then basifiy and extract with nonpolar solvent to get amine.

Was it over basified (too high pH) or too strong of base (saturated NaOH)?

Is that brown clump a nasty tar?

It seems strange that there is less chloroform than what was originally added.

What kind of crazy side reactions could be going on?

Does tryptamine smell like DMT, is that smell particular to indoles in general?

Can this be saved?

Sorry if this seems rushed, it is.”

So…….from this small amount of info any bee have any comments?
Thank you so much, any thoughts and speculations are welcome.


  • Guest
« Reply #1 on: May 18, 2004, 12:12:00 PM »
"Is glycerin a suitable for this?"

As glycerine decomposes upon boiling at atmospheric pressure I'd say no, not really.

"Is this appropriate reasoning?>If one has an amine in an alcohol, then basifiy and extract with nonpolar solvent to get amine."

Generally no, since many alcohols are soluble in the NP (glycerol is not soluble in chloroform however). Getting rid of the alcohol and keeping the water, then extract with NP is the usual way to go.

"It seems strange that there is less chloroform than what was originally added."

Some of the NP will dissolve in the water phase, it's not a problem if you do several extractions though.

"Can this be saved?"

There are lots of functional routes on The Hive, UTFSE and you'll see...


  • Guest
Mineral oil is a good solvent for this kind of
« Reply #2 on: May 18, 2004, 04:05:00 PM »
Mineral oil is a good solvent for this kind of thing. It's inert, clean, and very high boiling AFAIK.


  • Guest
Re: decarb question session
« Reply #3 on: May 18, 2004, 05:40:00 PM »
Was it over basified (too high pH) or too strong of base (saturated NaOH)?

Possibly yes, chloroform, upon contact with concentrated alkali, forms dichlorocarbene.

What kind of crazy side reactions could be going on?

Alpha-aminoacids turn into cyclic diketopiperazines when heated to a too high temp. Chloroform with alkali and primary amines could form isonitriles.

Does tryptamine smell like DMT

Tryptamine, as well as DMT and DET smells like plastic. The smell differs a little from one substance to another.

is that smell particular to indoles in general?

No  :)

From SWIM's experience, procedure with cyclohexen-2-one in cyclohexanol worked, but his maximum yield was 5,5 g of the tryptamineHCl from 15 g D,L-tryptophan, possibly due to overacidifying and heating TxHCl in an aqueous hydrocloric acid for some time during the workup. All the tryptophan did not dissolve during the decarboxylation, half of it remained unchanged after the sixth hour.

Swim wonders about possible mechanism of this reaction. Could imine, where the lone pair of amine nitrogen is delocalised on that double bond of ketene, be one of the important intermediates?


  • Guest
OK here are my personal tryp decarb newbee...
« Reply #4 on: June 27, 2004, 03:54:00 PM »
OK here are my personal tryp decarb newbee questions:

Does anyone know if MEK can be used instead of cyclohexenone? If this is the case: which solvent should be used then? Tetralin? Or maybe toluene/xylene? What about high boiling alcohols like n-nonanol (bp 215°)?



  • Guest
Won't do.
« Reply #5 on: July 05, 2004, 03:06:00 PM »
MEK and xylene/toluen won't work. Xylene and toluene have too low boiling points, not to mention MEK. I've tried it, the yield was about 2% or so.

Use MDP2P in tetralin, it should work  8)  ;)


  • Guest
this reaction is much trickier than it seems..
« Reply #6 on: July 05, 2004, 03:33:00 PM »
All these were tried by Yours Truly, and only resulted in tar, unreacted tryptophan, very low yields to no product at all, and the ever-present lingering smell of skatole:

DMSO/Trp copper chelate, DMSO/acetone, DMSO, turpentine/d-carvone, acetophenone and pyrolysis under vacuum.

It's amazing how much frustration this "simple decarboxylation" has cost me.


  • Guest
Oh my
« Reply #7 on: July 06, 2004, 06:07:00 PM »

didnt work? at all? that was to bee the last resort, ala "student"(see tryp decarb at rhodium)any details you feel like sharing are still appreciated

vary lame


  • Guest
not for me
« Reply #8 on: July 06, 2004, 08:07:00 PM »
But looking back I now have the impression that my stirring wasn't efficient enough. For Student's procedure you certainly need good overhead stirring.


  • Guest
« Reply #9 on: July 06, 2004, 11:09:00 PM »
would never think that that would be an issue, as long as there is nice reflux


  • Guest
there is an issue
« Reply #10 on: July 06, 2004, 11:51:00 PM »
As tryptophan will not dissolve in hot turpentine, you need to have a constant even distribution as you want as much surface area as possible exposed to the ketone-containing solvent, so that it can form the imine in a steady manner. Next to that, it will help a lot to drive the CO2 out of the reaction mixture.

If you omit stirring, you will encounter heavy bumping and the process will take forever and a day to complete.


  • Guest
Are there any reports of people who have ...
« Reply #11 on: July 07, 2004, 09:43:00 PM »
Are there any reports of people who have gotten this reaction to work? So far I've only read about failures.


  • Guest
« Reply #12 on: July 08, 2004, 08:26:00 AM »
I'm successfully decarboxylated DL-tryptophan (DMSO, menthone+acetone). Reaction completes at half a hour.
Pictures and procedure (w/pictures, on russian):

Post 509654 (missing)

(dennis_pro: "Èëëþñòðèðîâàííîå äåêàðáîêñèëèðîâàíèå", Russian HyperLab)


  • Guest
Your reaction mixture seems to be reddish...
« Reply #13 on: July 08, 2004, 09:03:00 AM »
Your reaction mixture seems to be reddish right from the start. What's the trick to get it working?


  • Guest
How have you tested if it is indeed tryptamine
« Reply #14 on: July 08, 2004, 10:15:00 AM »
How have you tested if it is indeed tryptamine and not a cyclization product?


  • Guest
tryptamine carbonate
« Reply #15 on: July 08, 2004, 05:22:00 PM »

Post 512109

(jemma_jamerson: "purifying tryptamine and co2", Tryptamine Chemistry)

Patent US2943093

gives a method for purifying tryptamine compounds by treatment with CO2 in a solvent to form the carbonate which precipitates from the solution. CO2 is in the air. I wonder if this could cause problems when handling tryptamines. Tryptamine carbonates tend to be insoluble in solvents like alcohol and methylene dichloride. Heating the tryptamine carbonate decomposes it into the tryptamine and CO2.

Maybe you should try this out on the product you've obtained..


  • Guest
crude translation of dennis_pro's post
« Reply #16 on: July 08, 2004, 06:33:00 PM »
My Russian isn't what it used to be anymore  :) , but here is a translation of Dennis_pro's post:
(I'll include the pictures too)

(HyperLab Bee)
05-26-04 05:23

Post 509654 (missing)

(dennis_pro: "Èëëþñòðèðîâàííîå äåêàðáîêñèëèðîâàíèå", Russian HyperLab)

Illustrated decarboxylation
(Rated as: excellent)

As the catalyst was used menthone, which was obtained by the oxidation of menthol using potassium dichromate in the presence of sulfuric acid, employing the general procedure as described in Organikum.

20 g DL- tryptophan was placed into the flask, equipped with a reflux condenser and stirrer (? don't see one on the pictures -VV) , and there was added 50 ml of dimethylsulfoxide (pharmaceutical grade "dimexid"), followed by a solution of 0.5 ml menthone in 5 ml of acetone, and, using good stirring (caution: evolution of carbon dioxide, strong frothing!) was heated to 150-180°C for an hour (actually the reaction already subsided after 30 min).
(That last part of the sentence, is that correctly translated? "????????? ??? 150-180? ? ??????? ????"))

30 minutes after the reaction started boiling, there was added through the condensor 5 additional ml of acetone (the vapors of acetone protect the reaction mixture from oxidation by atmospheric oxygen). When the reaction was finished, the solution became completely transparent and the evolution of carbon dioxide ceased.

The resulting pink coloured solution was allowed to cool and was diluted with 200 ml water, causing the mixture to become cloudy and the base of tryptamine is liberated in the form of a red oil.

70% acetic acid was added which led to the complete dissolution of oil. This was neutralized with sodium bicarbonate until no more CO2 was evolved. This caused part of resins to float together with the foam. The mixture was filtered through cotton, which removed floating resins. Nevertheless, the solution remained a red color. For a more complete removal of resins the mixture was washed with a small quantity of dichloromethane.

Aqueous NaOH was added, which caused the mixture to become cloudy, and after standing overnight tryptamine precipitated, which was filtered off and dried. Tryptamine obtained this way will still contain traces of NaOH. Attempts at washing the precipitate on the filter with water will lead to the significant losses of tryptamine as a result of its significant solubility in the water (34 g/l).

Since tryptamine possesses significant solubility in the water, it is better to extract the resulting alkaline suspension of tryptamine three times with benzene. Extracts are pooled and dried with anhydrous MgSO4, and to this is added just enough petroleum ether to turn the solution cloudy, and the solution is left overnight in the refrigerator. During the night tryptamine is crystallized in the form of completely colorless needles.

/zavtra I will report this fotku, forgot krassota:) / The general output not of schitan, since with the experiments separation of candy (tryptamine) from govna resin) product threw out itself on nemnogu into the toilet. Procedure will be improved on the following week, with the application of the almost inert gas:)

P.S. The use of the organic (?) solvents, acetic acid and bicarbonate is compulsory, an attempt at the acidification by sulfuric acid, and the extraction of resin by petroleum ether did not succeed, since resins and tryptamine in it were left mostly undissolved.
Attempts to directly basify the solution and to immediately extract tryptamine with benzene lead to the isolation of red noncrystallizing resin:



  • Guest
« Reply #17 on: July 08, 2004, 07:42:00 PM »
Muito agradável! Vitus, você é o mais melhor!  ;D


  • Guest
FOOK YA!!! (i hope)
« Reply #18 on: July 08, 2004, 08:05:00 PM »
ok, dare i ask? yes, what are the yields?


  • Guest
From Rrrraaashhia with love ;-)
« Reply #19 on: July 08, 2004, 08:14:00 PM »
Dos Agradecimentos GC_MS!  ;D

Now, my impression is that the small amount of menthone is not the relevant ketone, but much more so acetone, although considering its low boiling point this would be quite unlikely too.

Let's say there is 3 mmol of menthone available for every 100 mmol tryptophan, compared to the 68 mmol acetone in which the menthone was added. Maybe it would be a good idea to add 5 ml acetone every 5 minutes or so?

Also... --> ?? ?????????? ??????  :)  
You didn't tell us what your final yield was..