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otherwhitemeat
Registered: 10/25/06
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Loc: Florida
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Psilocybin mushrooms produce harmala alkaloids! 1
#26345706 - 11/25/19 10:06 PM (4 years, 4 months ago) |
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Psilocybin mushrooms also produce MAOIs (harmala alkaloids). Can’t believe this is becoming known only now in 2019: https://www.ncbi.nlm.nih.gov/pubmed/31729089 . That’s right, the specific combination of DMT (4-HO) and harmalas that make ayahuasca through plant-blending artifice is made within mushrooms all by themselves. Psilohuasca may be at least somewhat redundant.
This has major implications for understanding of dose-effect curves, extraction and preservation methods, and the non-equivalency of synthetic or pure psilocybin/psilocin and whole mushrooms. Let’s say you wanted to patent a synthesis method, or regulate away from whole fungal bodies the way some parties have wanted to isolate THC from all the messy other plant components of cannabis: reductivist error. Even says the harmalas are concentrated in the hyphal apices, which are mainly in the mycelium but some in the stipes. So you’re missing out if you think caps are where it’s at or you trim the stipes too much.
Full article behind paywall but I might just part with $9 to read it. Or try this: https://sci-hub.tw/downloads/2019-11-15/39/10.1002@chem.201904363.pdf
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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breeg89
i'll tell ya hwhat
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: otherwhitemeat]
#26345751 - 11/25/19 10:27 PM (4 years, 4 months ago) |
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Very cool. I bet the perceived differences between stuff like 4-AcO-DMT and mushrooms is due to the presence of MAOIs in the mushrooms, rather than differences in metabolism between psilocbin and 4-AcO-DMT
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Alan Rockefeller
Mycologist
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: breeg89] 2
#26345930 - 11/26/19 01:33 AM (4 years, 4 months ago) |
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Quote:
breeg89 said: Very cool. I bet the perceived differences between stuff like 4-AcO-DMT and mushrooms is due to the presence of MAOIs in the mushrooms, rather than differences in metabolism between psilocbin and 4-AcO-DMT
I don't think there is enough MAOI's in the mushrooms to have any effect - the mycelium has 100x more.
See also https://www.shroomery.org/forums/showflat.php/Number/26321428
Other exciting psilocybin news also came out of Germany this week - the identity of the blue staining compounds have been elucidated.
See https://www.shroomery.org/forums/showflat.php/Number/26322744
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PsychoReactive
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: Alan Rockefeller]
#26345990 - 11/26/19 03:25 AM (4 years, 4 months ago) |
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Is it why you can eat them and trip as oppose to eating DMT and no able to have any effects?
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ReynardTheFox
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: PsychoReactive] 1
#26346271 - 11/26/19 08:22 AM (4 years, 4 months ago) |
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No. most people eat very little mycelium when they eat mushrooms. Also, synthetic psilocybin has been used in clinical studies to wondrous effect. Not to burst anyone bubble, but the effects of the maoi on psilocybin's effectiveness are probably not as strong as you might think. Or at least the mushroom effects you are currently used to don't have much to do with the maoi. I don't know many people who shovel mycelium into their mouths when eating shrooms.
A good way to test the effects of the maoi on potency would be to take a batch of mushrooms and eat a specific dose of only caps (which would have little or no mycelium) and then later after tolerance has disappeared take the same dose of only stems (which will almost certainly have mycelium at the base). Perhaps even ever so slightly increase the dose of the stems to account for psilocybin-lacking mycelium weight. If the stems make you trip harder then that might be some indication of maoi potentiation. However, doing this test only once and with only one person wouldn't yield very reliable data. Psilocybin effects are too varied from trip to trip regardless of dose, and yes, even tolerance.
-------------------- "Every actual State is corrupt. Good men must not obey laws too well" - Ralph Waldo Emerson "If I am the devil's child, I will live then, by the devil" - Ralph Waldo Emerson
Edited by ReynardTheFox (11/26/19 08:53 AM)
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Failboat
Fuck Up
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: ReynardTheFox]
#26346631 - 11/26/19 12:03 PM (4 years, 4 months ago) |
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What about the fuzzy feet?
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Fractal420
Psycellium
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: Failboat]
#26347822 - 11/27/19 02:46 AM (4 years, 4 months ago) |
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Thats FAE
-------------------- Dreaming of That face again. It's bright and blue and shimmering. Grinning wide And comforting me with it's three warm and wild eyes. Prying open MY third eye
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pablokabute
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: PsychoReactive]
#26348045 - 11/27/19 07:01 AM (4 years, 4 months ago) |
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Quote:
PsychoReactive said: Is it why you can eat them and trip as oppose to eating DMT and no able to have any effects?
No. Psilocybin metabolizes to Psilocin. Psilocin is simply a DMT molecule with an extra oxygen molecule which could be the main reason it gets absorbed thru the guts and not easily destroyed. I suspect that extra oxygen molecule binds the whole Psilocin molecule together but I could be wrong.
Edited by pablokabute (11/27/19 07:04 AM)
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Lucis
Nutritional Yeast
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: otherwhitemeat]
#26348955 - 11/27/19 04:12 PM (4 years, 4 months ago) |
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Another source here.
There are many mysteries surrounding psychedelic mushrooms (aka psilocybin mushrooms or magic mushrooms). One of the most critical questions is very basic; what compounds do these mushrooms contain? Historically, psilocybin (the most abundant compound) has received much of the attention. Psilocybin is a prodrug that the body metabolizes to psilocin, the compound that acts at the serotonin 5-HT2A receptor to produce the psychedelic effect.
Over the years, researchers have identified other compounds in magic mushrooms such as psilocin, baeocystin, norbaeocystin, and aeruginascin. Now, with the renewed interest in the possible therapeutic uses of psychedelics, scientists are revisiting magic mushrooms at a fundamental level—figuring out what compounds are in them.
Study Finds ß-Carboline Compounds in Magic Mushrooms German scientists have identified new compounds in four species of magic mushrooms and studied their roles in biosynthetic pathways the mushrooms use.1 The researchers isolated the known magic mushroom compounds psilocybin, psilocin, baeocystin, norbaeocystin, and norpsilocin. The new compounds they isolated belong to a family of chemicals known as ß-carbolines.
ß-carbolines are naturally occurring alkaloid compounds.2 They are most commonly known as components of the psychotropic beverage ayahuasca. Examples of ß-carbolines include harmine, harmane, and harmaline (ß-carboline is also another name for the compound norharmane).
Much of the effect of ayahuasca is due to the ability of ß-carbolines to inhibit MAO (monoamine oxidase) enzymes.2,3 This inhibition makes it possible for the psychedelic compound DMT (dimethyltryptamine, another compound in ayahuasca) to pass out of the digestive system and enter the circulation.
ß-carbolines has some psychotropic effects on their own. Still, without their ability to inhibit MAO enzymes, the full effects of ayahuasca are not realized. ß-carbolines also inhibit the uptake of serotonin, dopamine, epinephrine, and norepinephrine via competitive inhibition of the receptors4,5 (Keep in mind that the interactions between an enzyme and a molecule are different from how an allosteric modulator interacts with a molecule).
From a disease standpoint, ß-carbolines are known to play a role in the development of essential tremor (uncontrolled shaking) and have been implicated in Parkinson’s disease.6
Magic Mushroom Synthesize Several ß-Carbolines Using 1D and 2D NMR (nuclear magnetic resonance) spectroscopy, Blei et al. analyzed extracts from Psilocybe cubensis, P. mexicana, P. cyanescens, and P. semilanceata. They identified these ß-carbolines in the extracts: Cordysinin C, Cordysinin D, Harmane, Harmol, Norharmane, and Perlolyrine. Figure 1 shows their chemical structures. These compounds have previously been isolated from fungi and plants in genera such as Cordyceps, Peganum, and Banisteriopsis.
As part of this study, the researchers used stable-isotope labeling with 13C11-L-tryptophan to show the ß-carbolines were biosynthetic products of the Psilocybe species. This means that ß-carbolines in magic mushrooms may contribute to the entourage effect along with the known compounds. As the researchers put it,
We conclude that Psilocybe mushrooms produce an ayahuasca-like and potentially similarly synergistic set of metabolites that may impact upon onset and duration of their effects. 1
Also, using MALDI-MS (matrix-assisted laser desorption/ionization mass spectroscopy), the researchers showed that the ß-carbolines accumulated at the hyphal apices (the outer edges of the mycelium).
The Effects of Magic Mushrooms vs. Individual Molecules The Blei et al. paper is a pioneering step in studying the chemistry and variability of the compounds in magic mushrooms. This work highlights the chemical complexity of naturally occurring compounds. It helps with the understanding that ingesting magic mushrooms is very different from taking pure psilocybin (or any other single compound isolated from magic mushrooms). The pharmacology of mushrooms is different than individual compounds and understanding this is critical for optimizing the effects of formulations of magic mushroom compounds.
As is often the case with scientific discovery, these study results answer some questions but also pose more. The presence and known effects of ß-carboline compounds in the Psilocybe species they studied, displays the entourage effect in magic mushrooms in a new light. The study authors sum this up well by saying,
Future pharmacological research is therefore warranted to determine to what extent Psilocybe β-carbolines contribute to the actual psychotropic effects of magic mushrooms.
-------------------- ©️
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Fractal420
Psycellium
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: Lucis]
#26350001 - 11/28/19 06:08 AM (4 years, 4 months ago) |
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mushrooms can at least be taken with (or among) other medicines, which would be dangerous with regular maoi’s
And no, the reason they work orally is because 4ho/4po-Dmt (psilocybin and psilocin) are fully active orally.
-------------------- Dreaming of That face again. It's bright and blue and shimmering. Grinning wide And comforting me with it's three warm and wild eyes. Prying open MY third eye
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pablokabute
Hari ng Amag
Registered: 11/22/11
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Loc: rural ghetto
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: Fractal420]
#26350250 - 11/28/19 09:26 AM (4 years, 4 months ago) |
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Quote:
Fractal420 said: mushrooms can at least be taken with (or among) other medicines, which would be dangerous with regular maoi’s
And no, the reason they work orally is because 4ho/4po-Dmt (psilocybin and psilocin) are fully active orally.
from what I remember, all psilocybin becomes psilocin first before it passes thru the guts, nervous system and eventually pass thru the blood-brain barrier.
-------------------- Fermented Mushrooms!! --- https://www.shroomery.org/forums/showflat.php/Number/23378638/fpart/1/vc/1 'The second seal: “All CONTAMINATED things and events are unsatisfactory.”' "I envy you. You North Americans are very lucky. You are fighting the most important fight of all - you live in THE HEART OF THE BEAST." --Anonymous Guerilla, or is he..
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blackout
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: ReynardTheFox]
#26350766 - 11/28/19 03:31 PM (4 years, 4 months ago) |
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Quote:
ReynardTheFox said:I don't know many people who shovel mycelium into their mouths when eating shrooms.
there are plenty of reports of people eating colonised grains which proved to give a strong effect.
Recent thread on it here https://www.shroomery.org/forums/showflat.php/Number/26303098
Another guy grew on "soft agar" 1/10th the regular amount of agar is used. https://www.shroomery.org/forums/showflat.php/Number/7680608
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ReynardTheFox
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: blackout]
#26350823 - 11/28/19 04:13 PM (4 years, 4 months ago) |
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Quote:
blackout said:
Quote:
ReynardTheFox said:I don't know many people who shovel mycelium into their mouths when eating shrooms.
there are plenty of reports of people eating colonised grains which proved to give a strong effect.
Recent thread on it here https://www.shroomery.org/forums/showflat.php/Number/26303098
Another guy grew on "soft agar" 1/10th the regular amount of agar is used. https://www.shroomery.org/forums/showflat.php/Number/7680608
Thanks for the info. From what I understand though, only very few strains produce very active mycelium, whereas the maoi content in most strains is supposed to be pretty high (100x more than in the fruits according to Alan). My guess is its not the maoi thats particularly active or potentiating relative to the psilocin/psilocybin effects.
-------------------- "Every actual State is corrupt. Good men must not obey laws too well" - Ralph Waldo Emerson "If I am the devil's child, I will live then, by the devil" - Ralph Waldo Emerson
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Fractal420
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: ReynardTheFox]
#26351362 - 11/29/19 02:08 AM (4 years, 4 months ago) |
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Well hey if you wanna eat colonized grains feel free. Maybe you’d trip balls but I wouldn’t do it. I’d imagine it would be much harder to consume. But yes imagine all the psilo that goes into the mushrooms but eating a whole flush at once (If that’s how it even works, I don’t know). My guess is it all starts as DMT which becomes 4-PO and 4-Ho in the mushrooms but it’s gotta start somewhere.
Maybe by eating Myc you are consuming dmt psilo and Maois. And probably large amounts. Still. Bleh. I have enough trouble consuming mushrooms (I like tea and other non-direct methods)
-------------------- Dreaming of That face again. It's bright and blue and shimmering. Grinning wide And comforting me with it's three warm and wild eyes. Prying open MY third eye
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blackout
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: ReynardTheFox]
#26355036 - 12/01/19 06:42 AM (4 years, 4 months ago) |
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Quote:
ReynardTheFox said: From what I understand though, only very few strains produce very active mycelium
I have read nothing that convinced me that any of the species would not work. I would specifically want to see people saying they ate X amount after growing it out for 2+months, and I would want to believe that person is telling the truth as some would have reason to deceive.
In the thread I linked one said
Quote:
don_shadow said: I recently heard a report from a trusted friend that the mycelium of Panaeolus cyanescens is not potent enough to be of any use in this application, so check that one off the list. Howdy Asura!
There was no info given there, and another poster had strongly recommended pan cyan as being very potent.
Time is definitely a factor, so the previous report might have been from somebody who did not leave it long enough.
You will find plenty of posts saying cubensis myc will not work, you have to be careful as many are parroting what they heard, or possibly deliberately misleading & lying to people as they do not agree with the practice -which I also consider dangerous so can understand where they are coming from.
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musiclover420
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: Fractal420]
#26355666 - 12/01/19 02:21 PM (4 years, 4 months ago) |
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Quote:
Fractal420 said: mushrooms can at least be taken with (or among) other medicines, which would be dangerous with regular maoi’s
Not necessarily. The MAOI's being referenced here are the same type of reversible MAOI's found in Ayahuasca, they are very dose dependent and considerably less dangerous compared to modern non reversible MAOI's.
They are dangerous to combine with various medicine, but only at large enough doses. Most people are also probably avoiding eating mushrooms on SSRI's or other sketchy meds that would be the most dangerous with the harmalas.
So it's possible they'd be present in mushrooms enough to add to the effects but not enough for full on MAOI effects, which aren't even necessary to make the mushrooms orally active. It could still effect the experience or duration however.
Also the beta carbolines discovered in mushrooms do seem to be a bit unique:
Quote:
Cordysinin C, Cordysinin D, Harmane, Harmol, Norharmane, and Perlolyrine.
The harmalas found in Ayahausca tend to be more Harmaline/harmine and Tetrahydroharmaline. So this blend could be considerably different.
I don't know much about Cordysinin or Perlolyrine offhand but they could have some distinct properties from the beta carbolines found in Aya.
A quick search says perlolyrine is apparently found in Sake and Soy Sauce β‐Carbolines from Japanese Sake and Soy Sauce
Not seeing much info on it though. Cordysinin C is apparently found in Cordyceps not seeing much info in it either though.
-------------------- Don't worry about me, I've got all that I need. And I'm singing my song to the sky You know how it feels, With the breeze of the sun in your eyes. Not minding that time's passing by I've got all and more, My smile, just as before. Is all that I carry with me I talk to myself, I need nobody else. I'm lost and I'm mine, yes I'm free
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Fractal420
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: musiclover420]
#26356572 - 12/02/19 02:00 AM (4 years, 4 months ago) |
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I get the feeling that any Maoi content isn’t too high in mushrooms.
I know people who do take SSRIs with mushrooms or have tried it. I think it’s the tricyclic antidepressants that are most dangerous with maoi’s
As for the 4aco thing, many people believe it is active on its own, and rather than just being a prodrug has its own properties. For one thing, 4aco is a lot more like dmt in the sense of it being extremely deep and quite visual. Also very unpredictable. Once it turns to psilocin, it’s prolly all the same as pure 4ho-DMT, but when you first get a new batch, 4aco IMO has an effect that is significantly different from mushrooms.
I find 4ho-Dipt very similar though. Much more so than -det or -met which can be really intense (And many think they’re awesome tryptamines) but seem to lack depth. For whatever reason I’ve only been able to source 4aco-DET but not really the 4ho. But usually 4hoMet. Either way, they’re definitely worthy substances but they don’t have the deep dive of 4aco-DMT or psilocybin
-------------------- Dreaming of That face again. It's bright and blue and shimmering. Grinning wide And comforting me with it's three warm and wild eyes. Prying open MY third eye
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LosTresOjos
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: Fractal420]
#26359231 - 12/03/19 02:27 PM (4 years, 4 months ago) |
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Wasn't it the nitrogen atom that curled the molecule and that would protect from it's destruction. I thought I heard Paul statment say this on the jre podcast
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Holybullshit
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Re: Psilocybin mushrooms produce harmala alkaloids! [Re: ReynardTheFox]
#26362799 - 12/05/19 11:20 AM (4 years, 4 months ago) |
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Quote:
ReynardTheFox said:A good way to test the effects of the maoi on potency would be to take a batch of mushrooms and eat a specific dose of only caps (which would have little or no mycelium) and then later after tolerance has disappeared take the same dose of only stems (which will almost certainly have mycelium at the base). Perhaps even ever so slightly increase the dose of the stems to account for psilocybin-lacking mycelium weight. If the stems make you trip harder then that might be some indication of maoi potentiation. However, doing this test only once and with only one person wouldn't yield very reliable data. Psilocybin effects are too varied from trip to trip regardless of dose, and yes, even tolerance.
I have a group of friends, who eat way more mushrooms and do more psychedelics in general than I do, most know little about pharmacology and less about organic chemistry....who swear up and down that caps and stems give you a different trip, some of them prefer caps and some prefer stems.
Before now I always thought it was psychogenic or placebo, or some sort of self-fulfilling prophecy that keeps spreading to new and transient members of this social circle. But maybe they are onto something.
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