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Microwave-assisted Tryptophan decarboxylation into Tryptamine Options
 
Hailstorm
#1 Posted : 2/5/2021 6:17:31 AM

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Disclaimer: this post does not describe a synthesis that involves closely watched or highly dangerous materials.

The following tek allows synthesizing tryptamine (T) from L-Tryptophan with no deep knowledge of chemistry or expensive equipment. T should not be confused with DMT (N,N-dimethyltryptamine) - T is not psychedelic and therefore legal in most of the world. Although DMT can be made from T rather easily, doing so is outside the scope of this thread.

The spoiler below contains information about the equipment and ingredients.

The instructions are below. It takes a while to get it right, so please allow for some learning-by-doing, and feel free to ask questions.

Decarboxylation

1. To a small boiling flask add 4.0 g Tryptophan powder and 15 mL Carvone (or spearmint essential oil). Stopper the flask but ensure there is a small hole for CO2 to escape through.
2. Gently microwave the flask at ~250-300 W (enough to reach the boiling point, not too much to cause an eruption) for ~3-4 minutes (longer if you are using spearmint oil). Stop immediately after the mixture becomes transparent, with little or no unreacted tryptophan powder at the bottom.
3. Stopper the flask airtight (keep as much CO2 inside as possible) and let the mixture cool down to room temperature. Avoid contact with air or acids.

Tryptophan forms an imine with Carvone, which decarboxylates into T imine, releasing carbon dioxide.

The red hue is due to decomposition products (indole, skatole, etc.) dissolved in carvone.

Low power and short reaction time are necessary to minimize the thermal decomposition of T. If the mixture is brown, opaque, and smells like feces - you have overheated it.


Extraction

4. At room temperature, add 30 mL of 10% AcOH and stir the mixture for 5-10 minutes at a very high speed. The emulsion should look homogeneous and orange while mixing, but will separate into 2 layers whenever you pause: a yellow aqueous layer at the bottom, a darker organic layer at the top.
5. Pre-wet filter paper with water and pour the entire mixture through the filter into another small flask. The acidic extract will pass through the filter and should be collected, while the dark hydrophobic liquid will be retained and can be discarded.

T imine gets protonated and dissolves in the aqueous layer.

The pre-wetted paper acts as a membrane that slows the organic liquid down. This trick only works with liquids that are poorly soluble in water. If your paper is too porous, use a pair of paper filters instead of one.

If you want to increase the yield you can perform three smaller (3 x 10 mL) extractions instead of one larger extraction (1 x 30 mL): after collecting the aqueous extract place the filter on the empty reaction flask and puncture the paper to drain the organic liquid back.


Hydrolysis (recommended)

6. Insert a thermometer into the flask with the filtered acidic extract. Add a thin layer of heptane to shield the dissolved T from atmospheric oxygen. With very slow stirring, bring the temperature to 70-75 °C and keep it in that range for ~10 minutes. A dark layer will appear and thicken on top while the rest of the mixture will gradually become semi-transparent - you will begin to see the magnetic stir bar and the tip of the thermometer. Cool the mixture down to room temperature.
7. Filter the mixture through pre-wetted filter paper (just like you did in step 5). Sprinkle the filter with a bit of fresh AcOH to push all T through. The collected filtrate should be transparent yellow.

The elevated temperature accelerates T imine hydrolysis into T and Carvone from a day at room temperature to a few minutes at 70 °C.

A thermometer adapter with a thermometer in it can help you minimize contact with air.

With a hotplate stirrer you could try to save time by combining the extraction and hydrolysis steps: heat the reaction mixture up and stir it at 70-75 °C for 10+ minutes at maximum speed, filter through a pair of wet paper filters.


Workup

Salt route (easier)

8a. With medium-speed stirring, slowly saturate the acetic acid solution with NaCl (about 26 g NaCl per 100 mL of 10% AcOH). Only add more salt after the previous batch dissolves (when stirring becomes quiet again). If drops of Carvone appear on top, soak them out with a small piece of paper towel. Crude T hydrochloride (T·HCl) will begin to precipitate early, but you should continue to add NaCl. After the entire planned amount has been added, allow stirring to continue for some time to dissolve as much NaCl as possible.
9a. Filter the precipitate through filter paper, dry and weigh it.
10a. Optionally, recrystallize T·HCl from boiling MeOH: 1 g pure T·HCl dissolves in ~9 mL boiling MeOH (so you will need a bit more MeOH to dissolve impure T·HCl). Filter any undissolved solids out. Add seed T·HCl crystals or scratch the inner side of the flask to promote crystallization. Stopper the flask to prevent evaporation. Allow the solution to cool down to the room temperature. After several hours move it to a refrigerator. A few hours later - to a freezer; leave it there overnight. Filter off-white T·HCl crystals (picture attached): about 79% will be recovered, 21% will remain dissolved in MeOH.
11a. Wash T·HCl with fresh ice-cold MeOH from the freezer, dry and weigh it.

NaCl has reverse solubility in MeOH, so it will not precipitate when cooled down.

It is possible to recrystallize T·HCl from anhydrous ethanol instead of methanol, but larger volumes of ethanol will be required. T·HCl is soluble in water, so it is possible to recrystallize it from ethanol-water mixtures, but losses in water will be substantial.


Freebase route (harder)

8b. With continuous stirring, add NaOH pellets to the acidic solution very slowly, letting the mixture cool down before adding more. As T begins to precipitate, the color will change from clear yellow to cloudy yellow. Around pH 9-10 the color will change again - to pale orange, you will see droplets of carvone floating around - a lot of them, if you skipped the hydrolysis step above.
9b. Filter the mixture through a pre-wetted cotton ball. Squeeze the cotton to push the last drops out. The filtrate should be cloudy white.
10b. Continue to add NaOH until pH goes well above 12. Filter and dry precipitated T. Depending on your technique, its color (and purity) will vary from snow-white to off-white to pale yellow.
11b. To get rid of microscopic NaOH crystals, wash T with ice-cold concentrated ammonia.
12b. Optionally, recrystallize T freebase from very large amounts (liter per gram) of hot/boiling n-Heptane. T recrystallized from heptane is snow-white. A Soxhlet extractor is a convenient device for purifying T without large amounts of heptane or manual effort.

The residual T imine undergoes alkaline hydrolysis into T and Carvone. Carvone droplets and T particles coalesce into sticky goo. Cotton fibers capture that goo, and the remaining T will precipitate clean.

You will need to develop a sense for when (at what pH) to perform the final filtering. If you filter too soon, not all carvone will precipitate, and your final product will not be snow-white. If you take pH too high before filtering, too much T will precipitate and get trapped in the cotton ball.

Concentrated (10-28%) ammonia is basic enough to keep T in the freebase form, has enough water to dissolve NaOH, and evaporates away cleanly as water vapor and ammonia gas.


Storage

T freebase will darken when exposed to light, heat, and oxygen. It is therefore best stored in a closed container in a freezer. T hydrochloride appears to be resilient to oxidation.

Conversion

T hydrochloride can be converted to T freebase by dissolving it in a small amount of ice-cold concentrated ammonia, filtering and drying the precipitate.
T freebase can be converted to T hydrochloride by dissolving it in diluted (5-10%) acetic acid and salting out as described in step 8a above.

Purification

T freebase can be purified by either recrystallizing it from hot heptane (step 12b above) or converting it to T hydrochloride and back. T hydrochloride can be purified by recrystallizing it from boiling methanol (step 10a above).

Characterization

TLC
Rf = 0.45 (experimental, YMMV) in MeOH:conc.ammonia 7:1 v/v

Melting points (literature)

T: 118 °C
T·HCl: 254 °C

*** Photos ***

1) tryptamine hydrochloride recrystallized from boiling methanol
2) tryptamine freebase recrystallized from heptane (with a Soxhlet extractor)
Hailstorm attached the following image(s):
THCl.jpg (91kb) downloaded 143 time(s).
Tryptamine_Soxhlet.jpg (42kb) downloaded 56 time(s).
 

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Woolmer
#2 Posted : 2/6/2021 7:34:29 PM

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Thanks for sharing! This is very cool info for non-chemists like myself. Would just need to figure out what to do with Mr. T then Laughing
 
Hailstorm
#3 Posted : 2/7/2021 1:54:58 AM

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Woolmer wrote:
Thanks for sharing! This is very cool info for non-chemists like myself. Would just need to figure out what to do with Mr. T then Laughing

You are welcome!

You can use T to practice handling DMT, legally and inexpensively. T is quite similar to DMT in terms of properties: T is more basic, less soluble in heptane, melts at a higher temperature, but its behavior in acidic and basic environments is quite similar to that of DMT. For example, if you want to practice making or freebasing DMT fumarate, you can perfect your FASI technique on T fumarate first (T reacts with acetone, so FASA is not recommended).
 
grimlid
#4 Posted : 2/7/2021 7:28:46 PM

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https://www.talktofrank.com/drug/tryptamines
Would you consider this information accurate?
"I think; therefore I might be."
 
Hailstorm
#5 Posted : 2/7/2021 10:35:35 PM

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grimlid wrote:
https://www.talktofrank.com/drug/tryptamines
Would you consider this information accurate?

It looks accurate but overly simplistic as it attempts to describe an entire family of psychedelics in one article. There are dozens of tryptamines, and they are quite different.

To see what I mean, check out TiKHAL. It is written 24 years ago so it does not describe many novel tryptamines, but I am not aware of a newer work that would be just as comprehensive. In each chapter, skip the chemistry and read the subjective comments.
 
Woolmer
#6 Posted : 2/8/2021 11:24:36 AM

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Considering that there are so many different tryptamines, do you know of (or think there may exist) a synthesis that leads to a psychoactive tryptamine that is simple, relatively safe, and does not use watched chemicals?

I suppose since there is no common knowledge on this, that there does not exist such a synthesis. Surely it would often be discussed on forums like the nexus, or perhaps I am just being lazy in gathering info.
 
Hailstorm
#7 Posted : 2/9/2021 6:59:47 AM

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Woolmer wrote:
Considering that there are so many different tryptamines, do you know of (or think there may exist) a synthesis that leads to a psychoactive tryptamine that is simple, relatively safe, and does not use watched chemicals?

It depends on how you define "simple", "safe", and "watched".

"Simple" really depends on your knowledge and experience. What is simple to some folks on this forum would be beyond others' reach.

"Safe" is also very relative. Is lye safe? There is a horrific story on reddit about a NaOH particle getting stuck under someone's eyelid (he did not use goggles). Most non-polar solvents are toxic, so are most alcohols, etc.

"Watched" is a moving target that also depends on the country. Almost every compound, including tryptophan and acetone, is watched in the US - but there are different levels of "watched", so tryptophan is less likely to trigger an investigation compared to, say, iodine.

If we use the tek in this thread as a standard, then my answer will be "no, I am not yet aware of a full psychedelic synthesis that would be equally simple, safe, and legal". Both reductive amination and exhaustive methylation involve handling carcinogenic liquids and obscure lab chemicals, and therefore cannot be published and discussed here.

Quote:
I suppose since there is no common knowledge on this, that there does not exist such a synthesis. Surely it would often be discussed on forums like the nexus, or perhaps I am just being lazy in gathering info.

Nexus has a "no synthesis" rule - no synthesis that involves dangerous or watched chemicals can be discussed in the open.

The rule has its merits. If you lurk around a bit, you will see posts like this by people (children?) who are likely to hurt themselves and others by doing even traditional plant extractions. They are also unprepared legally and will incriminate themselves if the law enforcement knocks. A few busts or deaths linked to DMT Nexus - and the forum will be at risk; so much for psychedelic liberty.

The door is not closed completely - the rule just raises the bar on the safety of any synthesis that can be published here. As of 2021, to the best of my knowledge, nobody has been able to clear that bar. I am aware of an ongoing effort to produce a "Nexus-friendly" DMT tek, however.
 
benzyme
#8 Posted : 2/9/2021 12:52:49 PM

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This is a good thread Big grin
Hailstorm is correct, and made some excellent points regarding the responsibility that comes with the information.
I'll need to try this with limonene with a dash of PhAc. Microwave chemistry works best with solvents that lack a dipole, like limo, because they won't superheat. Limonene is used for microwave decarboxylation and extraction of cannabinoids, to great effect.

Tryptamine chemistry is tricky, what appears simple on paper, is not necessarily the case in practice. Transamidation reactions can occur with temps above 220 C, when decarboxylating. And that's just decarboxylating tryptophan.

Tryptamine hcl can be added to PF substrate, to boost psilocin/psilocybin content; 10-20 mM. Higher than that tends to stunt growth.

~aniracetam/pinoline
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
 
Woolmer
#9 Posted : 2/9/2021 4:58:14 PM

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benzyme wrote:
Tryptamine hcl can be added to PF substrate, to boost psilocin/psilocybin content; 10-20 mM. Higher than that tends to stunt growth.

This is very interesting. Do you have a link to a study on this? I have only been able to find one study by Jochen Gartz done in 1989 but it seems this has not been repeated quantitatively.
 
benzyme
#10 Posted : 2/9/2021 6:05:56 PM

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https://www.dmt-nexus.me...aspx?g=posts&t=79967
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
 
Woolmer
#11 Posted : 2/9/2021 6:28:04 PM

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Nice work! Seems blatantly ignorant of me to miss this. Apologies.
 
benzyme
#12 Posted : 2/9/2021 6:39:29 PM

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Woolmer wrote:
Nice work! Seems blatantly ignorant of me to miss this. Apologies.

Thanks.
And not at all. A search for common keywords probably wouldn't bring up that thread, or it would be buried in pages of search results.
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
 
famine
#13 Posted : 2/9/2021 11:29:03 PM

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Microwave is very interesting! Only a few minutes Wut? What yield do you get?
 
benzyme
#14 Posted : 2/10/2021 12:29:24 AM

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related thread https://www.dmt-nexus.me...spx?g=posts&t=62377

I may have uploaded an ebook on microwave-related chemistry. It is a well known method for pi-bond (double-bond) rearrangements, aka hydride shifts; and redox rxns. Microwave and ultrasonic emitters (ultrasound chemistry...I posted another thread on that).

further reading
https://b-ok.cc/s/microwave%20chemistry
https://booksc.org/s/microwave%20chemistry
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
 
benzyme
#15 Posted : 2/10/2021 12:59:11 AM

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This is my typical approach; nitrogen-purged reflux, 95:5 limo:acetophenone.
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
 
Fruit is life
#16 Posted : 2/10/2021 4:47:24 AM

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benzyme wrote:
This is my typical approach; nitrogen-purged reflux, 95:5 limo:acetophenone.


Woah..oneday I will have a lab like that, and hopefully the skill to know what I am doing with it all Laughing
The self that talks doesn't know, the self that knows doesn't talk.
 
Hailstorm
#17 Posted : 2/10/2021 8:52:49 AM

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famine wrote:
Microwave is very interesting! Only a few minutes Wut? What yield do you get?

I got 86% (2.7 g) beige (somewhat impure) T using one 30 mL extraction, freebase route (after step 10b).

This tek forgoes best practices like multiple extractions, inert atmosphere, etc. for simplicity. I would be happy with anything north of 50% as long as it is reasonably pure.

benzyme wrote:
I'll need to try this with limonene with a dash of PhAc.

I was actually inspired by studying aniracetam's/pinoline's many contributions Smile Invaluable was your reddit comment about T reacting with ethyl acetate, adding to the list of many gotchas.

Random notes:

Limonene's auto-ignition temperature is 237°C (for folks reading this: please be careful). I could not find the auto-ignition temperature for carvone.

I have come across an article that found isophorone to be the highest-yielding (higher than acetophenone). It is also cheap and somewhat less stinky. However, like acetophenone, isophorone is partially soluble in water, which makes the workup more tedious than just throwing everything into a piece or two of wet filter paper - one needs a sep. funnel or syringe/pipette, a wash with DCM/chloroform, etc.

Tryptophan in neat benzophenone results in a lot of decomposition products (indole, skatole), possibly from overheating due to benzophenone's high boiling point. Similar issues may arise with raspberry ketone - however, it is cheap and non-watched; there is conflicting data on whether it is soluble in water or not.

I do not know the rate of imine hydrolysis for acetophenone or isophorone. Carvone imine only begins to hydrolyze at an appreciable rate above 60°C. If acetophenone imine hydrolyzes at room temperature, during the acidic extraction step, that would be convenient. If not, then, unlike carvone, acetophenone formed via hydrolysis is going to remain dissolved in water, and a few non-polar washes may be necessary to drive the hydrolysis equilibrium.

L-Carvone has a faint, pleasant minty smell.

When I tried to pour acetic acid into the reaction mixture which was still too hot, the aqueous layer became green'ish. I'd be wary of producing beta-carbolines and therefore would not recommend heating the acidic extract above 70°C.
 
benzyme
#18 Posted : 2/10/2021 12:51:05 PM

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Hailstorm wrote:
benzyme wrote:
I'll need to try this with limonene with a dash of PhAc.

I was actually inspired by studying aniracetam's/pinoline's many contributions Smile Invaluable was your reddit comment about T reacting with ethyl acetate, adding to the list of many gotchas.


Thanks.
Like so many others, including yourself, I'm a student of Shulgin. So enamored by the process, I had to throw analysis in the mix, since I readily have the tools to do so. TLC is a great tool for preliminary studies; I don't have plates, I use HPLC instead. And as you undoubtedly have guessed, my avatar is the same on reddit and other boards. It's the mass analyzer, quadrupole ion trap.

I'm glad my work inspired others; some have used benzyl alcohol to good effect. Pugelone is also effective, not sure if anyone has used it yet. I did also crash out tryptamine extracted with dcm, by bubbling it with carbon dioxide, to get carbamate salts. I bet the microwave treatment would convert it back to the free base.
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
 
 
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