"Eloquent examples of this(Manipulation of Biosynthesis in organisms) are the delightfull reports of indole syntheses
that were explored in Germany over the last few years. Visualise a vigorous growing mycelium culture that is synthesising psilocin
by bringing together the natural DMT in it's diet with a vital but non-too discriminating enzyme that has the capacity for
putting a hydroxyl group onto a Tryptamine. The mycelium has the knowledge of how to 4-hydroxy-late something, but doesn't
really care what that something is. The available target for this skill, in the natural mushroom, just happens to be DMT.
The product is 4-hydroxy-DMT, or psilocin and this is what the organism makes, because this is all that can be made.
There is 1 starting material, there is 1 synthetic capability, and there is 1 product.

Now let's manipulate things a bit. Let's keep this little fungal factory going, but wash out the DMT and replace it with
something like DET. The hydroxylating compulsion appears to be still there and is quite intact. What happens?
The mycelium produces a bunch of 4-hydroxy-DET, an interresting compound and an active psychedelic, which was first
reported by Sandoz laboratories, but a compound that is unknown in nature. I will wager that if the mycelia were to
be sprinkled with MIPT, the enzyme system would produce 4-HO-MIPT which is fully as potent as psilocin and unrecognised
in any legal system in any country that I am aware of. You are exploiting a natural process by providing it with an
unnatural starting material, and allowing it to generate a product that is intrinsically unnatural."

Hai Nexians,

I was reading about Biosynthesis in the "DMT is everywhere" -Chapter of A.Shulgin's TIHKAL and this bit completely ignited my imagination.




Now for me this raises some questions.

1) If mushrooms need DMT in their diet to produce 4-HO-DMT, does that mean the most commonly used grow-materials for
psilocin mushrooms, like straw, riceflower & Cowdung, contain DMT?
(would explain why I find DMT's smell strangely similair to cowdung-smell to a degree )

2) What if I were to crush a handfull of Anadenanthera Colubrina seeds(very rich in 5-HO-DMT) to powder and sprinkle this
powder onto a growing mycelium and/or mix it into the straw/riceflower/cowdung/vermiculite-cake before innoculation...
What would the Magic mushroom make out of the given 5-HO-DMT?

3)Now what compound would a Psilocybe mushroom make if I fed it dried, powdered plant material rich in 5-MeO-DMT?


Has anyone here ever experimented with this? I really feel this subject needs more research.

Yes indeed Shulgin continues on the next page about how DMT is made in plants/fungi and the role of decarboxylases & N-methyl-transferases.
He mentions how Tryptophane is decarboxylated to produce Tryptamine, which in turn is converted by methylation into DMT.

I assume mushrooms produce DMT in the same way, except that they proceed to hydroxylate the DMT at the 4 position, creating psilocin.
So for psilocin-rich magic mushrooms you'd need a Tryptophan-rich substrate. Correct?

Does anyone have more specific information on the biosynthetic enzymatic steps/processes Psilocybe mushrooms use to produce Psilocin?

Of course this web site has a graphic showing the N-Methylation step first.

http://en.wikipedia.org/...locybin_biosynthesis.png

Now I ned to go back and double check some references because I really don't think mushrooms have significant quantities of DMT present and I'm pretty sure if the production was similar to the above link there would be DMT present.

However.... I have read reports of people spiking the substrate with tryptamine and dramatically increasing the potency...sorry don't have a link right now. This should allow the mushroom to produce Psilocin/Psilocybin at a rate equal to the next rate limiting enzyme catalytic step.

Don't believe everything wikipedia says...

The presence of both norbaeocystin and baeocystin in mushrooms argue that the methylation steps occur after the hydroxylation and phosphorylation steps.

If not this, then you'll have to assume that baeocystin and norbaeocystin are degradation by-products, which is difficult to envisage. You may also want to entertain the idea that the biosynthetic pathway of psilocybin is different from psilocin, i.e. whereas psilocybin is formed by the methylation of norbaeocystin and baeocystin, psilocin is formed by a dmt intermediate. But there's little if any evidence for any of the above.

It is far more likely that psilocin is a degradation product of psilocybin in mushrooms rather than a substrate for psilocybin, which makes the wiki diagram wrong. If methylation proceeds prior to hydroxylation, then you should be able to see DMT and NMT in mushrooms (which you don't) and if phosphorylation occurs in the end you should be able to see 4-HO NMT (which to my knowledge you don't).

I concur and that is essentially what I was proposing, but you never know. In all likelihood there is some trace amount of DMT in shrooms as the laws of statistical mechanics pretty much state that every reaction that can happen will happen in some capacity... In any event unless someone can show a journal article or other experimental evidence of significant quantities of DMT I'll stand bye the original biosynthesis I laid out in the prior post... Always good to have a sanity check with the other member though!

Gracias Amigo!

But another possible explanation for why you don't find 4-HO-Tryptamine and 4-HO-NMT in Magic Mushrooms could be if they decarboxylate Tryptophan into Tryptamine first,
then Methylate that Tryptamine into DMT and then 4-hydroxylate that DMT into Psilocin.

Shulgin specificly mentions the Magic Mushrooms 4-Hydroxylase enzyme being not-too-discriminating on what it 4-hydroxylates.
He also sais that sprinkling DET into the mycelium, makes the mushrooms growing from it produce 4-HO-DET.
I suppose he didn't make that up. I wish he had gone in more detail about this.

Are we hypothising about how mushrooms make psilocin because none of us is a biochemist? Or because simply no one really knows?

So do you think baeocystin and norbaeocystin are by products or stepping stones in the mushroom's enzymatic process to change a certain starting material into psilocyn?

I was just looking on Wikipedia at the Chemical constituents of Brown Rice & Barley; 2 plants often used to grow potent Psilocybe Mushrooms.
Both have a very high Niacin content(Vitamin B3) content. Looking at the moleculair structure of Niacin, it shows to bare a vague resemblence to
a Tryptamine-structure.

Could there be an enzymatic process in the Mushroom that turns Niacin into Psilocin stepwise and happens to form norbaeocystine & baeocystine in the process?
Niacin, in comparison to the Indole-ring structure, is missing the Benzene ring that Tryptamines have.
Could it be that the mushroom draws Benzene rings from other compounds in it's diet that it enzymatically breaks down and merges these Benzene rings onto Niacin molecules to form an Indole structure?

The original papers can be found on Shroomery over here, they documented up to a 300% increase in alkaloid production, iirc. There was a member of the nexus who successfully added tryptamine to his substrate about a year or a year-and-a-half ago and reported, in addition to an increase in potency, that the fruits were greatly mutated and dwarfed. His results seemed to confirm the old experiment and sounded rather impressive to me.

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.

Sister has also read about mushroom growers adding either tryptamine or DMT to their growing medium to make shrooms more potent, but has no first hand experience with it.