Psychoactivity of pure tryptamine (not N,N-DMT)

[RipNDip]

Hello, I'm a new member and not allowed to post into the "other entheogens" category yet so I thought I'd try here.
I'm interested if there is any psychoactivity of pure tryptamine (isolated as the hydrochloride salt) from the decarboxylation of L-tryptophan. I understand that bufotenin, melatonin, and serotonin are all tryptamine derivates (as well as the obvious DMT, and 5meo), so I'm curious if it would be metabolized to something like that, or have psychoactive effects if smoked or taken with an maoi. I've done some research on "pure tryptamine" but all results seem to just be people taking DMT. Does anyone have any experience with this, or have a good understanding of biology and know what would happen?

 

[atomu235]

As far as I know tryptamine can be decarboxylated in a solvent using a ketone. I don't know the exact details without doing some in depth research though. You may also need to figure out how to separate tryptamine afterwards as well as I doubt you'll get a high yield (silica column?, guessing at this point).

Have a look at Tihkal. It seems to be similar in effect to a low dose of LSD:

Erowid Online Books : "TIHKAL" - #53 T

Entry #53 T from TiHKAL by Alexander & Ann Shulgin.

www.erowid.org

I don't think anyone will be able to explain with certainty the metabolic path of tryptamine. It's really not well understood at this point in time.

 

[RipNDip]

Sorry I should have clarified, I've already preformed the synthesis and isolation of tryptamine. I was just interested if it had any psychoactivity as im expecting terrible yields converting it to N,N-DMT and am always interested in new compounds, especially those with very little research and understanding. The TiHKAL article answered my question perfectly, so thank you.

 

[Loveall]

Hello, did you do the decarboxylation with OTC chemicals? If yes and it does not violate this rule can you explain what you did? I ask because I'm getting ready to work on this using Limonene/MEK/spearmint essential oil (as a carvone source).

You may know this, but you could use the tryptamines you made in mushroom grows. Let the mushrooms do the hard methylating work with their wonderful enzymes. That's what I plan to do with it if I can make it from Tryptophan.

Thanks!

 

[benzyme]

there is an article which showed that even decarboxylation with a ketone catalyst resulted in cyclized products (beta-carbolines)...
the dreaded Pictet-Spengler cyclization.

here's another

 

[RipNDip]

Everything I used was OTC or made very easily from OTC chemicals, nothing used was controlled or very dangerous (so long as proper safety and handling procedures are used) so I feel it is ok to post these links.
Here are some methods of decarboxylation:

Tryptamine from Tryptophan - [www.rhodium.ws]

For the first link I would recommend the spearmint catalyzed method, as it only requires OTC materials

Sciencemadness Discussion Board - L-tryptophan decarboxylation - Powered by XMB 1.9.11

I have never tried the method discussed in the second link, but it seems simple enough and relatively cheap


Oh I've never heard about using mushrooms to methylate the tryptamine, I'll have to look into that as I have basically no experience growing mushrooms

 

[Loveall]

So turpentine and spearmint oil, right?

Looks ok in the first paper benzyme posted too (60%+ yield and no beta-carboline side reactions).

How did you do the workup?

 

[RipNDip]

It's relatively simple, all OTC expect for chloroform which can be made very easily from bleach and acetone. Id recommend distilling the spearmint oil to get pure carvone, I got better yield that way. It took a couple tries to fine tune everything and get the right boiling rate to prevent oxidation without solvent loss, but overall I reached around a 67% yield, which is alright.

 

[atomu235]

How did you check final product purity? Simple MP? Did you need to do any final clean up?

I'm very curious now and may attempt to replicate the procedure in the future. Until now I did not know about the ketone process side products at all... You learn something new every day

 

[RipNDip]

So far all I've done is check mp, but it has a very strong tryptamine smell which leads me to believe it was successful. Cleanup depends on the purity you desire, my first successful attempt I simply basified, chilled, and washed with ammonium, final product still is a bit yellow and mp is off by about 1.5°. It is still very pure and it is perfectly fine for most to stop here, as the impurities will be removed later upon methylation. However I was in search of the pure white 99.9% purity so I went a bit overboard with my second attempt and destroyed the yield. I heated the oil to around 80°C and washed 5 times with household vinegar, then slowing added NaOH until the pH was around 12 (stopping every so often to filter off junk that falls out of solution). The solution was then then placed in the freezer until crystals crashed out, and then was filtered and washed a few times with chilled ammonia. Finally I placed it into about 25ml of heptane and refluxed, once crystals started to appear at the boil line I transferred the heptane to a beaker where crystals crashed out of the orange-y solution, these were filtered and washed with ammonia. Final yield was about 0.43 grams from around 4g of the slightly impure tryptamine, so I would suggest skipping this complex cleanup.