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Simultaneous Production of Psilocybin and a Cocktail of β‐Carboline MAOI's in Shrooms

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Bancopuma

Bancopuma

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I've long suspected that there is more to mushrooms than just psilocybin, as I've personally found different species to vary consistently in experiential quality or character, and this has been echoed by many others...this study provides hints as for a possible reason for this, and why different species may vary.

Study:

Blei et al. (2019) Simultaneous Production of Psilocybin and a Cocktail of β‐Carboline Monoamine Oxidase Inhibitors in 'Magic' Mushrooms. Chemistry - A European Journal, In Press.

Abstract

The psychotropic effects of Psilocybe “magic” mushrooms are caused by the L‐tryptophan‐derived alkaloid psilocybin. Despite their significance, the secondary metabolome of these fungi is poorly understood in general. Our analysis of four Psilocybe species identified harmane, harmine, and a range of other L‐tryptophan‐derived β‐carbolines as their natural products, which was confirmed by 1D and 2D NMR spectroscopy. Stable‐isotope labeling with 13C11‐L‐tryptophan verified the β‐carbolines as biosynthetic products of these fungi. In addition, MALDI‐MS imaging showed that β‐carbolines accumulate toward the hyphal apices. As potent inhibitors of monoamine oxidases, β‐carbolines are neuroactive compounds and interfere with psilocybin degradation. Therefore, our findings represent an unprecedented scenario of natural product pathways that diverge from the same building block and produce dissimilar compounds, yet contribute directly or indirectly to the same pharmacological effects.
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Very interesting, but if I read it correctly, the amount of carbolines is very small to really contribute to the effects.
 
I've just been sent a copy of the whole paper, and am just about to hit the road for a few hours but I'm very intrigued to look into this in greater detail. Full paper is attached.
 

Attachments

  • Blei+et+al+2019_Simultaneous+Production+of+Psilocybin+and+a+Cocktail+of+_Carboline+MAOIs+in+Ma...pdf
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doubledog said:
Very interesting, but if I read it correctly, the amount of carbolines is very small to really contribute to the effects.
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Agreed, they are quoting ~ug/g yields. I don't see how beta carbolines could have an effect in that range, unless I'm missing something (?).

Interesting anyway.
 
Just to clarify for anyone interested, while the occurrence of these compounds in the mushroom species is certainly interesting, it is worth noting that the concentrations of these ẞ-carbolines was indeed very low, with 1.6 micrograms per gram of P. mexicana mycelium), so one would ingest around 5-8 micrograms of harmine with a 2-5g dose of fungal material...whereas an active dose of harmane in pharmahuasca would be around 50 milligrams, and such a dosage would be 10,000-fold higher than that found in the mushroom. The actual P. cubensis mushrooms contained 100 fold less concentration than the P. mexicana mycelium, in other words 100,000th of the usual ẞ-carboline dose, so this is not going to be pharmacologically relevant.
 
I personally suspect something does, even if it isn't down to this. The researchers behind this have the view that the "secondary metabolome of these fungi is poorly understood in general." No doubting the power of external set and setting factors...but I tend to find quite clear differences between species, and these differences in experiential qualities are often consistent...for me, P. azurescens, P. cubensis and Panaeolus cyanescens are all highly distinct from each other...but some of the traits in signature/qualities are consistent across trips. Even basic potency data we have on the Psilocybe genus is out of date, in the past having used old, dried samples which likely were degraded, and these days we have access to higher precision analytical techniques. So definitely more work to be done here...we don't yet even have clear data on whether psilocybin analogue baeocystin is active in humans or not.
 
Another question that has come up is mannitol. It's present in mushrooms and can affect the blood-brain barrier osmosis. We have a thread suggesting to add mannitol to mushrooms to see if anything changes (kicked off because of some experiments done in rats).

Of course, the quantities in natural mushrooms may not be enough to make a difference and mannitol intestinal absorption is not trivial (rats were injected with it). There are reports that lemon juice can enhance mannitol absorption which may be part of why people like the lemon tek.

I did buy pure mannitol, but it's been in the pantry for months and I haven't touched it yet.
 
Even basic potency data we have on the Psilocybe genus is out of date, in the past having used old, dried samples which likely were degraded, and these days we have access to higher precision analytical techniques. So definitely more work to be done here...we don't yet even have clear data on whether psilocybin analogue baeocystin is active in humans or not.
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Yes agree with this. Would be nice to get more up to date data in this area.

Another question that has come up is mannitol. It's present in mushrooms and can affect the blood-brain barrier osmosis. We have a thread suggesting to add mannitol to mushrooms to see if anything changes (kicked off because of some experiments done in rats).
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Its certainly possible ingredients in mushroom could effect bioavailability / pharmacokinetics of psilocybin / psilocin. Interesting discussion.
 
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