Growing Synthetic Tryptamines Naturally

Hedgeclipper · Apr 9, 2012

I'm not entirely sure where to post this due to its very cross-catagory nature. it sort of fits into synthetic drugs, mushroom cultivation and both organic and synthetic compounds, but I like the input I get from you guys and this is my favourite forum so I'm going to post here

I've always liked the idea of being a DIY Shaman and growing/creating your own psychedelic compounds so I've recently been working on a medium-sized hallucinogenic mushroom grow with a friend.

We're fruiting in monotubs on coco coir/perlite and injecting the spored (albino A+ psylocybe cubensis) on a millet substrate. Since I got access to a serious autoclave -- instead of a shitty pressure cooker -- my success rate has been growing mycelium has drastically increased.

Now I've recently been reading into Ethocybin (4-PO-DET), a homologue of Psylocybin which apparently has a shorter duration but similar affects to those of mushies. Upon further research, this stuff basically is converted into 4-HO-DET in the body and, similarly to the relationship between 4-PO-DMT (psylocybin) and the 4-ACO-DMT we all know and love, we can also have 4-ACO-DET (which I have access to) hydrolyze into 4-HO-DET for the same result in humans.

Strangely I have never looked into this compound before, but I opened up TiHKAL and found that the 4-HO-DET entry is one of shulgins most interesting:

Some fascinating studies have been done in Germany where the metabolically active mycelium of some Psilocybe species have been administered diethyltryptamine as a potential diet component. Normally, this mushroom species dutifully converts N,N-dimethyltryptamine (DMT) to psilocin, by introducing a 4-hydroxyl group into the molecule by something that is probably called an indole 4-hydroxylase by the biochemists. You put DMT in, and you get 4-hydroxy-DMT out, and this is psilocin. Maybe if you put Mickey Mouse in, you would get 4-hydroxy-Mickey Mouse out. It is as if the mushroom psyche didn't really care what it was working with, it was simply compelled to do its sacred duty to 4-hydroxylate any tryptamine it came across. It was observed that if you put N,N-diethyltryptamine (DET, not a material found in nature) into the growing process, the dutiful and ignorant enzymes would hydroxylate it to 4-hydroxy-N,N-diethyltryptamine (4-HO-DET) a potent drug also not known in nature. This is the title drug of this commentary. What a beautiful burr to thrust into the natural versus synthetic controversy. If a plant (a mushroom mycelium in this case) is given a man-made chemical, and this plant converts it, using its natural capabilities, into a product that had never before been known in nature, is that product natural? What is natural? This is the stuff of many long and pointless essays.
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(from grampa Shulgin)

So for someone like me who is successfully growing quite a few jars of mycellium this brings up many interesting possibilities. I'm starting to get thinking about all the different things that could be added to our substrate since the fantastic psylocybe enzymes seem to be able to accomplish so much. Everything from adding many different tryptamines to the mix, to adding 5-HTP or DMT-containing mimosa hostilis rootbark and producing either extra-potent mushrooms or mushrooms containing whole new naturally produced (but not naturally occuring) alkaloids. I read through a few of the Dr's blog posts and find this interesting one:

However there is a very interesting study that took place in Leipzig about 15 years ago. Jochen Gartz, a mushroom explorer whom I know quite well, has done some fascinating studies with Psilocybe species by raising them on solid media containing strange tryptamines that are alien to the mushroom. Apparently the enzymes that are responsible for the 4-hydroxy group of psilocin are indifferent to what it is they choose to 4-hydroxylate. He has taken things like DPT or DIPT and put them in the growth media and the fruiting bodies that came out contain 4-hydroxy-DPT or 4-hydroxy-DIPT instead of psilocin. In fact, he has a patent on the process. These active compounds are made by the mushroom so they really are natural and yet they never have been observed in nature. I'll give you even odds that if you put spores of a psilocybe species on cow droppings loaded with 5-MeO-DMT you would come out with mushrooms containing 4,5-HO-MeO-DMT. This way you avoid a 10 step synthesis by growing a psychoactive mushroom that contains no illegal drug.
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(http://www.cognitiveliberty.org/shulgin/blg/2005/12/4-hydroxy-5-methoxy-nn_07.html)

Now I would like to do some experiments to see what different things we could manage to create with the fantastic psylocybe mycelium. Although my initial interest was sparked from the 4-PO-DET possibilty, we could just order 4-ACO-DET in order to get 4-HO-DET to our brains, but with the method that the germans created 4-PO-DET, we could make all sorts of other fantastic things:
-add 5-meo-DMT -> 4,5-HO-MeO-DMT
-add AMT -> 4-HO-AMT and maybe even have some methylation occur and get 4-HO-a,n-DMT (or TMT) (and the same could be done with 5-MeO-AMT)
-add mimosa hostilis or 5-HTP -> not sure, but I feel it might increase potency and/or yield. I've heard of good results in other experiments
-add DiPT?
-add DPT?

If I could access any chemical analysis equipment it should be a rather simple experiment with some potentially very interesting results. I am particularly interested in the possibility of producing 4-hydroxy-DPT, as I have a very special relationship with this compound.

EDIT: For those who'd like to read more into it, here is a nice study with some good references that you guys could look into: (I found it posted in an old thread on drugs-forum)

BIOTRANSFORMATION OF TRYPTAMINE IN FRUITING MYCELIA OF PSILOCYBE CUBENSIS.

Jochen Gartz
Institute of Biotechnology, Academy of Sciences of the GDR,
Permoserstrasse 15, GDR-7050 Leipzig, German Democratic Republic
Received: March 13, 1988
ABSTRACT
Mycelial cultures of Psilocybe cubensis, with the ability to form psilocybin and psilocin de-novo, also hydroxylated and methylated fed tryptamine to give psilocin in up to 3.3% dry mass of the obtained fruit bodies. By using HPLC and TLC, it was found that these mushrooms contain only a small amount of psilocybin (0.01-0.2% dry mass). The values of psilocin are the highest described in any mushrooms.
INTRODUCTION
Psilocybe cubensis (Earle) Sing, is a subs-tropical mushroom and contains the indole alkaloid psilocybin and only small amounts of its dephosphorylated counterpart psilocin (1-4). Variations in these metabolites have been well demonstrated by investigations of fruit bodies cultivated under controlled conditions of a rye-grain medium (2) and rice substratum (3), respectively.
The study of psilocybin biosynthesis in submerged culture of P. cubensis showed that radioactive tryptamine functioned as a better precursor than tryptophan (5-7). It was found that not less than 22.4% of the psilocybin formed was derived from the labeled precursor tryptamine (5). The level of psilocin was generally zero in the mycelial tissue from these experiments (5-7).
In the present paper, the bio-transformation of fed tryptamine in fruiting mycelia of Psilocybe cubensis is described.
MATERIALS and METHODS
Cultivation of Psilocybe cubensis
A dried cow dung/rice-grain mixture (2:1) with twice the amount of water was used to obtain fast fructifications without casing of a strain (3) of Psilocybe cubensis . A 25 mM concentration of tryptamine (as hydrochloride) was added to this medium. Cultivations without the addition of tryptamine were also tested. The methods of cultivations were described in (3).
The first sporocarps were produced by cultures of Psilocybe cubensis in 3 to 4 weeks. The cultures continued to produce mushrooms in five flushes. Each flush was harvested as soon as the sporocarps were mature. The mushrooms were immediately freeze-dried, sealed in plastic, and stored at -10 degrees C until analysis.
EXTRACTION and ANALYSIS The extraction procedure and the analysis of the indole alkaloids by using HPLC and TLC were described in the previous papers (3,8-10). The presence or absence of tryptamine was demonstrated by TLC as described by Stijve et al. (11).
RESULTS and DISCUSSION
The cow dung-rice mixture actually produced the first flush of mushrooms earlier than the cultivations on ry (with casing) (2) and rice (3), respectively. They yielded an average of 3 g dry mass per 10 g substratum.
Under the same culture conditions, the fructification times, the yields, and sizes of the mushrooms as well as the bluing feature (3) were equal when the growth media also contained high concentrations of tryptamine. Initial experiments without the addition of tryptamine were performed to determine the content of psilocybin and psilocin in comparison with experiments using other culture conditions and/or media (2,3).
The levels of psilocybin and psilocin varied from one flush to the next, but generally were much the same as those in the other experiments (2,3) (table 1). Consistently low levels of psilocin were found in the mushrooms without the addition of tryptamine to the substratum. Additionally, psilocin generally was absent in the first flush as was also observed in earlier investigations (2,3). Table 1 shows that the fed tryptamine gives high values of psilocin in each flush from the cultures.
Table 1 Variation of psilocybin and psilocin levels in Psilocybe cubensis as a function of flush number from the cultivations with (a) and without (b) addition of tryptamine (25 mM concentration).

Flush no. Psilocin Psilocin Psilocybin Psilocybin
a b a b 1.2.1 - 0.01 0.55 2.3.30.010.020.48 3.2.80.020.20.51 4.3.10.090.070.46 5.2.90.150.130.61 These psilocin levels are uncommonly high (from 2.1 to 3.3%) since values reported for psilocin in dried mushrooms are always below 1% (1-4,12,13).
Inocybe Aeruginasens Babos contains only traces of psilocin but high amounts of the incompletely methylated psilocybin (baeocystin) (9). In contrast to the intitial experiments without an addition of tryptamine, the mushrooms generally contained only small amounts of psilocybin. The tryptamine level was always zero in each mushroom. In this case no tryptamine was additionally found in the methanolic extract of the vegetative mycelia from the substratum.
In a previous report, Gartz (3) was unable to detect baeocystin in P. cubensis. But Repke et al. (14) reported traces of baeocystin in other strains of Psilocybe cubensis about 10 years ago. They suggested that many non-specific enzyme systems exist in fungi which have the ability to oxidise exogenously added compounds, as well as normal, obligatory intermediates (14).
The results in Table 1 show that the enzyme systems in Psilocybe cubensis have a high hydroxylation and methalation capacity to convert added Tryptamine to psilocin. It is possible that a reduced amount of phosphate in the culture media decreased the bio-synthesis of psilocybin from psilocin in the media.
P.cubensis also failed to produce detectable amounts of baeocystin under these culture conditions.
Acknowledgments
The author thanks the following persons: G. Drewitz, T. Stijve, G.K.Muller, and M. Gey who generously supplied valuable information.
REFERENCES
Heim, R., Hoffman, A. (1958) Compt. Rend. 247,557.
Bigwood, J.. Beug, M.W. (1982) J. Ethnopharm. 5, 287.
Gartz, J. (1987) Beitrage zur Kenntnis der Pilze Mitteleuropas 3, 275.
Badham, E. (1984) J. Ethnopharm. 10, 249
Agurell, S., Blomkvist, S., Catalfomo, P. (1966) Acta Pharm. Suecica 3, 37.
Agurell, S., Nilsson, J.L.G. (1968) Acta Chem. Scand. 22, 1210.
Agurell, S., Nilsson, J.L.G. (1968) Tetrahedron Lett. 1063.
Gartz, J. (1985) Pharmazie 40, 134.
Gartz, J. (1987) Planta Med. 53, 539.
Semerdzieva, M., Wurst, M., Koza, T., Gartz, J. (1986) Planta Med. 52, 83.
Stijve, T., Hischenhuber, C., Ashley, D. (1984) Z. Mykol. 50, 361.
Beug, M.W., Bigwood, J. (1982) J. Ethnopharm. 5, 271.
Ohenoja, E., Jokiranata, J., Makinen, T., Kaikkonen, A., Airaksinen, M.M. (1987) J. Nat. Prod. 50, 741
Repke, D.B., Leslie, D.T., Guzman, G. (1977) Lloydia 40, 566.
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Anyways, any input you guys have on this idea would be greatly appreciated
4-Hydroxy-DPT could be a very interesting thing ideed...

IslandHippie · Apr 9, 2012

I have no ideas, but am interested in what you are experimenting with, and look forward to hearing about the results with what you try.

Hedgeclipper · Apr 9, 2012

Well I probably won't be doing too much of this (aside from maaybe adding mimosa hostilis rootbark to the substrate) for another month or two, as I'm going treeplanting and my grow-op will be on hold while I get my summer work done. When I get back, though, I should have more investment money and I am planning on doing a lot more experimentation and increasing the size of my grow-op with a martha (a shelving unit full of trays) in addition to the 3 monotubs I already have.

For the moment I'm just trawling for ideas and working on a detailed experimenta procedure. More studies/academic references would be useful aswell.

Isn't the concept of growing compounds that don't occur in nature through a natural process fascinating? What would we call them? Semi-synthetic? Semi-organic? I'm not sure but I like what Shulgin has to say about it: "This is the stuff of many long and pointless essays"

IslandHippie · Apr 14, 2012

Changing the outcome of a fungus with chemicals would be genetic modification, wouldn't it?

CannbisSouL · Apr 14, 2012

I am pretty sure it would not be genetic modification.

The mushrooms are genetically designed to 4-hydroxylate whatever tryptamines are in their growing medium. All this experiment does is introduce a new variable to the growing game.

Genetically modifying the mushrooms would be like changing their genetics to 5-Methoxylate (I don't even know if that is possible) any tryptamine that you were to have in the substrate.

The Real Peter Parker · Apr 19, 2012

Sounds possible from your sources, it would be really cool if you had access to a place tests whats in the shroom.

Except wouldn't you need to add a lot of chemical to have enough for the mushrooms to take it in and produce? Possible waste?

It would be interesting to compare mushrooms grown on a certain chemical to normally grown mushrooms taken with that chem?

The Real Peter Parker · Apr 19, 2012

CannbisSouL said:

Changing the outcome of a fungus with chemicals would be genetic modification, wouldn't it?
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I am pretty sure it would not be genetic modification.
All this experiment does is introduce a new variable to the growing game.
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Its like if you fed a cat all spinach and another all cat food, not genetic modification. Selective breeding is the only "genetic modification" example I can think of, and I'm not even sure if that's accurate.

Hedgeclipper · Apr 21, 2012

The Real Peter Parker said:

Sounds possible from your sources, it would be really cool if you had access to a place tests whats in the shroom.

Except wouldn't you need to add a lot of chemical to have enough for the mushrooms to take it in and produce? Possible waste?

It would be interesting to compare mushrooms grown on a certain chemical to normally grown mushrooms taken with that chem?
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I may be able to do some tests on the mushrooms, not sure, but maybe. And, yes, there could be a minor waste of tryptamines, but its for science so its okay.

I would really like to try mushrooms with 4-hydroxy-DPT in them.

pr0ne420 · Apr 21, 2012

cool shit dude

The Real Peter Parker · Apr 24, 2012

Can't wait for results

guerillabedlam · Oct 12, 2012

I know you haven't been on HF for a couple weeks but this thread randomly entered my consciousness and I'm curious if you have followed up on some of these ideas, so thought I'd bump it.

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