downwardsfromzero
Boundary condition
Do you have the means to analyse for these compounds? Otherwise the experiment is just a way of making growing mushrooms a slightly more expensive hobby.SKA said:
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Biosynthesis of Novel Tryptamines Aspirations.
- Thread starter SKA
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Hieronymous
Rising Star
I've only skimmed this thread so apologies if I'm off the mark.
A large part of this discussion regarding mushrooms seems to focus on the alkaloids present in the fruit bodies of the mushrooms, are there any known metabolic pathways that could utilise mycelium to produce DMT as a metabolite excreted from the mycelium ?
ie could mycelium be doped with a precursor to produce alkaloids as a waste product that doesn't appear in the fruit bodies ?
A large part of this discussion regarding mushrooms seems to focus on the alkaloids present in the fruit bodies of the mushrooms, are there any known metabolic pathways that could utilise mycelium to produce DMT as a metabolite excreted from the mycelium ?
ie could mycelium be doped with a precursor to produce alkaloids as a waste product that doesn't appear in the fruit bodies ?
Hieronymous said:
Psilocin = 4-HO-DMT. Psilocybin = 4-PO-DMT.
It is theorised that DMT is an intermediary product of the
mushroom's biosynthesis of Psilocin & Psilocybin, but that is theory and no more.
AFAIK DMT has never been found in magic mushrooms.
That COULD be because, for instance, the DMT produced by mushrooms gets so quickly converted into Psilocin & Psilocybin that DMT levels never build up to the quantity where it becomes detectable by chemical analysis.
So even assuming DMT indeed IS an intermediary product in the mushroom's process of making 4-HO-DMT & 4-PO-DMT, you would somehow have to shut down the enzymes that 4-hydroxilise Tryptamines and the enzymes that 4-Phosphoryloxy-ate Tryptamines. Then you MIGHT get DMT containing mushrooms, but even if that is enzymatically possible the question remains wether the mushrooms could still grow & survive without these enzymes.
That in itself is already a long-shot, let alone making mushrooms/mycelium excrete DMT.
Talking about DMT excretions: I was talking about DMT plants & fiddling around with their Enzymes with a friend of mine who studies Biochemistry. I was suggesting taking an easy & fast growing DMT-producing plant, like Phalaris, & significantly raising it's DMT content by feeding it nutrients that would boost the enzymatic activity of the Enzymes it uses to biosynth DMT. This guy is also learning alot about genes. Learning to splice DNA, RNA, Isolate components of cells, basic genetic manipulations...etc
He suggested that this could be done by taking out or significantly surpressing the inhibiting factors that normally limit the speed of DMT production & the quantity of DMT produced in these plants. Basically making their DMT-producing mechanism go double or triple speed & power... If that could be done effectively, the plants may indeed become so DMT-rich that after a certain point DMT would "proliferate" the plant matter and be excreted in the surfaces of it's leaves, stems, flowers...etc.
But that is a different topic altogether. Fascinating, but different from this topic, which is to feed Psilocybin Mushrooms unusual Tryptamines in hopes they enzymatically turn these into unusual analogues of Psilocin & Psilocybin.
Nathanial.Dread
Esteemed member
No clue. You'd probably end with with some kind of 4-HO-5-MeO substituted tryptamine, but I have no idea how the enzymes would treat the acetyl group.SKA said:
If you could cleave the acetyl group from the amine, you could get 5-MeO-tryptamine, and if you fed THAT to the mushrooms, you could probably end up wiht 4-HO-5-MeO-DMT (assuming, of course, that the pathway is Tryptamine -> oxidation -> 4-HO-Tryptamine -> methylation -> 4-HO-N,N-DMT).
If that's possible (and all of this is, in fact, true), that sounds to me like the most cost-effective rout towards 4-HO-5-MeO-DMT)
SKA said:
what he's not mentioning is that it's not sustainable in future generations. progeny revert back to wild-type genetics.
it's similar to what has been observed with mutated strains of claviceps spp.
the same is true for mushrooms. each generation has to be treated with precursors, or genetic modification...yes, the nmt->dmt->baeocystin step is spontaneous and irreversible, so manipulating DMT production isn't the issue. Dope 'em with NMT or tryptamine.
as far as feeding them melatonin, I don't think the sterics of the end product would elicit any central activity.
downwardsfromzero
Boundary condition
4,5-MDO-N-alkyltryptamines appear to hold more promise than 4-OH-5-MeO-N-alkyltryptamines, especially if one looks at the parallels in the phenylethylamine worldbenzyme said:
But that becomes a different ball game unless one finds the enzyme and/or corresponding gene for the reverse of the MDO- ring-opening reaction that occurs in various metabolic systems.Clearly, numerous plants are capable of forming benzodioxole ring systems and AFAIK this is usually from a methoxy group adjacent to a hydroxy group. Whether this would work for indoles ultimately depends on the enzyme(s) concerned.
What examples of 4,5-MDO- and 4-OH, 5-MeO-tryptamines are there in the plant world?
Apologies here for a bit of an off-the-top-of-the-head ramble!
datdmt
Rising Star
im really interested in using a tryptamine 4-hydroxylase inhibitor within the substrate. would i be correct in assuming that if you theoretically inhibited the psilocin step, then the enzymes responsible for psilocybin would not convert the DMT into anything? this would be 10x easier than even attempting to isolate enzymes,putting them into vectors and expressing them inside E. coli. i have already found an inhibitor discussed in a peer reviewed paper.
Fenclonine - Wikipedia .as well as the chemical p-ethynylphenylalanine
this is medicine that acts to inhibit the creation of serotonin by inhibiting tryptophan hydroxlase, and with serotonin being a tryptamine , is it safe to assume that tryptophan hydroxylase is the enzyme responsible and not tryptamine hydroxylase. what im asking is, are those the same thing?
this could also prove or disprove the theory of DMT being a intermediary product.
edit: i also just found this 4-Chloro-DL-phenylalanine readily available online. its also a tryptophan hydroxylase inhibitor. i would really like to hear some feedback on this. i am quite excited.
Fenclonine - Wikipedia .as well as the chemical p-ethynylphenylalanine
this is medicine that acts to inhibit the creation of serotonin by inhibiting tryptophan hydroxlase, and with serotonin being a tryptamine , is it safe to assume that tryptophan hydroxylase is the enzyme responsible and not tryptamine hydroxylase. what im asking is, are those the same thing?
this could also prove or disprove the theory of DMT being a intermediary product.
edit: i also just found this 4-Chloro-DL-phenylalanine readily available online. its also a tryptophan hydroxylase inhibitor. i would really like to hear some feedback on this. i am quite excited.
Nathanial.Dread
Esteemed member
Given that phosphyrlation seems to happen before methylation, the question becomes whether the enzymes that methylate the tryptamine molecule will still work with the hydroxyl or phosphoryl group is not present.
I say go for it though. That sounds excellent.
I say go for it though. That sounds excellent.
datdmt
Rising Star
I've done enough research to conclude that psilocin IS vaporizable. So I will experiment with this first. If hyperspace is achievable with pislocin. Then it would be fair enough to say that psilocin is superior to DMT. It would be a lot of work to even see the results of tryptophan hydroxylase inhibitor. Thin layer TLC , controlled studies and lots of time. Etc etc. for those of us who have no availability of DMT , vaping pislocin would be a stellar alternative.
Nathanial.Dread
Esteemed member
Psilocin freebase is pretty hard to get ahold of, unless you have a synthesis. There's been talking here on The Nexus about trying to find a working extraction, but that hydroxyl group makes things kind of difficult.datdmt said:
You might be able to put some dried up mushrooms in an electric vape though.
All the best
~ND
It is highly unlikely that a drug that inhibits a mammmalian enzyme would ever work on a fungal one. Despite the fact that the latter has a similar activity to tryptophan hydroxylase, the mammalian and the fungal hydrozylases have different substratesand different productsaanf chances are that they share very little sequence similarity.datdmt said:
Also, tryptophan hydroxylase and tryptamine hydroxylase are not the same thing.
SKA said:
Hello SKA, did you ever try this? If yes, What happened? Thank you.
benzyme mentioned that the central position may not be affected in post #45:
benzyme said:
I think this applies to 5-position substituted tryptamines. If so, this means 4-OH may not attach due to the 5-MeO interfering with the psiH enzyme (today we know the enzymatic pathways thanks to the paper published in 2017).
So with melatonin in the substrate this may happen:
Melatonin-> 5-MeO-MT + CO2 (this is catalized by the enzyme psiD and could be a rate limiting step)
5-MeO-MT + 2 SAMe -> 5-MeO-DMT + 2 SAH (catalized by psiM)
So you could get 5-MeO-DMT as inmotion mentioned earlier in this thread. Once upon a time shulgin said you could get 4,5-HO-MeO-DMT (see Ask Dr. Shulgin Online: 4-Hydroxy-5-methoxy-N,N-dimethyltryptamine, Psilocybe mushrooms, Psilocin )
Either way you would probably get something interesting by feeding mushrooms melatonin.
PS: Thanks to werd for pointing me to this interesting thread
Loveall said:
On the other hand, if the mushrooms can attach a 4-OH group to a 5-OH substituted tryptamines (5-HTP or bufotenine) they may produce the neurotoxin 4,5-dihydroxytryptamine.
Even though this may not happen, since the possibility exists, I am not going to pursue this and would recommend to proceed with caution if someone really want to do this. Thank you.