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Invisible4HO-DMT
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Editor’s Choice Award – Best Psychedelic Chemistry/Synthesis Study of 2020 * 1
    #27113909 - 12/29/20 11:24 AM (27 days, 18 hours ago)

Interesting that baeocystin is a prodrug for norpsilocin.


Article


Quote:

As the year comes to a close, Psychedelic Science Review is acknowledging some of the best research papers of 2020. So much has been learned this year that it’s difficult to choose the one best study in any category. However, based on the overall impact of the work in the chemistry/synthesis category, one study stood out.

The Editor’s Choice Award for the best psychedelic chemistry/synthesis paper of 2020 goes to Dr. Alexander Sherwood of the Usona Institute and his research team, who developed a synthesis method for making the magic mushroom compound psilocybin and four of its lesser-known analogs; norpsilocin, aeruginascin, baeocystin, and norbaeocystin.1 Additionally, the study evaluated the compounds using several biological tests, providing some first-ever data and observations in the growing field of psychedelic science.

In March 2020, Psychedelic Science Review summarized the paper written by Dr. Sherwood and his team shortly after it was published in the Journal of Natural Products.

The authors noted a key improvement made in their synthesis method compared to previous work. It eliminates the need to purify the compounds using chromatography. Their method isolates the compounds by precipitating them from a pH-adjusted aqueous solution via the addition of acetone.

Of the biological tests that Sherwood et al. performed on the analogs, two findings are especially critical to psychedelic science. First, they discovered that norpsilocin is more potent than psilocin (the bioactive form of psilocybin) at the serotonin 5-HT2A receptor. Also, they confirmed that baeocystin is a prodrug of norpsilocin.

Second, Dr. Sherwood and his team observed that baeocystin is not psychedelic when compared to psilocybin using the mouse head twitch response (HTR) test. Psilocybin induced the HTR in a dose-dependent manner. However, the effects of baeocystin in HTR testing were indistinguishable from those mice given saline.

The researchers hypothesized that baeocystin might not cross the blood-brain barrier due to the phosphate group it has in position 4 of the tryptamine ring. However, when baeocystin undergoes dephosphorylation in the body, it becomes norpsilocin, which they observed is more potent than psilocin.

This study has advanced psychedelic science by providing general synthesis routes for four of the minor tryptamine compounds present in magic mushrooms. For the first time, this work gives scientists meaningful access to these compounds for further study.

Also, Dr. Sherwood and his team conducted biological testing on some of these compounds for the first time. This testing is essential for understanding the pharmacology of all the psychedelic and non-psychedelic compounds in naturally occurring organisms like magic mushrooms. Applying these testing practices to future work could make a difference in harnessing the full benefits of psychedelic compounds.




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InvisibleHolybullshit
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Re: Editor’s Choice Award – Best Psychedelic Chemistry/Synthesis Study of 2020 [Re: 4HO-DMT]
    #27114038 - 12/29/20 12:32 PM (27 days, 17 hours ago)

Wow I was just referring to this study, in a comment on how, to me, MAOI's change a mushroom trip rather then just potentiating them.


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Invisibleopenmind
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Re: Editor’s Choice Award – Best Psychedelic Chemistry/Synthesis Study of 2020 [Re: 4HO-DMT]
    #27114276 - 12/29/20 02:41 PM (27 days, 15 hours ago)

Quote:

Quote:

4HO-DMT said:
Interesting that baeocystin is a prodrug for norpsilocin.






....they discovered that norpsilocin is more potent than psilocin (the bioactive form of psilocybin) at the serotonin 5-HT2A receptor. Also, they confirmed that baeocystin is a prodrug of norpsilocin.







That is super interesting!

We've known about baeocystin being present in some mushrooms for a long time now, yeah?...But we're just now learning that it is a prodrug for an alkaloid that is even more potent than psilocin !?


So psilocybin is to psilocin, as baeocystin is to norpsilocin....

....and norpsilocin is even more potent than psilocin!



So it's possible for mushrooms that have relatively low levels of psilocybin & psilocin to still be "potent" if they contain enough baeocystin(?).

Makes me wonder what norpsilocin is like by itself, its mechanism of action and how it would feel compared to psilocin. Or how it contributes to the effects/trip one experiences.

I wonder if we'll see any "RCs" based of baeocystin or norpsilocin?




While IME I haven't really noticed much of any difference between "strains" or species of mushrooms, but it does seem like over the recent years we're learning more about the alkaloid profile of mushrooms that points towards some species definitely having some unique activity/alkaloid profile.

Aren't there only a few species that produce baeocystin beyond miniscule trace amounts?








Quote:

Holybullshit said:
Wow I was just referring to this study, in a comment on how, to me, MAOI's change a mushroom trip rather then just potentiating them.






Totally!

I find that things like rue or caapi bring different "layers"/aspects to the experience and "modulate" the experience, rather than just potentiating and extending the duration of the trip.






-OM

.


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Invisible4HO-DMT
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Re: Editor’s Choice Award – Best Psychedelic Chemistry/Synthesis Study of 2020 [Re: openmind]
    #27114815 - 12/29/20 08:27 PM (27 days, 9 hours ago)

Quote:

openmind said:
That is super interesting!

We've known about baeocystin being present in some mushrooms for a long time now, yeah?...But we're just now learning that it is a prodrug for an alkaloid that is even more potent than psilocin !?


So psilocybin is to psilocin, as baeocystin is to norpsilocin....

....and norpsilocin is even more potent than psilocin!




Yeah, it seems so. I think it's pretty cool that this research is finally being done.



Quote:


Quote:

Holybullshit said:
Wow I was just referring to this study, in a comment on how, to me, MAOI's change a mushroom trip rather then just potentiating them.






Totally!

I find that things like rue or caapi bring different "layers"/aspects to the experience and "modulate" the experience, rather than just potentiating and extending the duration of the trip.






-OM

.




Here is a link to another article that goes into a bit more detail on the same study.

They suggest that norpsilocin is inactive in the presence of MAO.

Quote:

The authors attribute the lack of activity by norpsilocin in the HTR test to the action of monoamine oxidase enzymes (MAO). MAOs use oxygen atoms to remove amine groups from molecules. They noted that secondary amines tend to be broken down readily by MAOs compared to tertiary amines.4 Therefore, they hypothesize that norpsilocin (secondary amine) gets degraded faster in the body compared to psilocin (tertiary amine).

The authors summed up their observations by saying, "…baeocystin and norpsilocin may be rendered inactive by metabolism before reaching targets in the central nervous system."




So, taking rue or caapi would probably activate norpsilocin. Maybe that is why psilohuasca is reported to have a different feel? It might be the activation of norpsilocin!?

Neat stuff! I hope this research continues to get funding and evolves!


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Invisibleopenmind
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Re: Editor’s Choice Award – Best Psychedelic Chemistry/Synthesis Study of 2020 [Re: 4HO-DMT]
    #27116114 - 12/30/20 12:43 PM (26 days, 17 hours ago)

Quote:

4HO-DMT said:


Here is a link to another article that goes into a bit more detail on the same study.

They suggest that norpsilocin is inactive in the presence of MAO.

Quote:

The authors attribute the lack of activity by norpsilocin in the HTR test to the action of monoamine oxidase enzymes (MAO). MAOs use oxygen atoms to remove amine groups from molecules. They noted that secondary amines tend to be broken down readily by MAOs compared to tertiary amines.4 Therefore, they hypothesize that norpsilocin (secondary amine) gets degraded faster in the body compared to psilocin (tertiary amine).

The authors summed up their observations by saying, "…baeocystin and norpsilocin may be rendered inactive by metabolism before reaching targets in the central nervous system."




So, taking rue or caapi would probably activate norpsilocin. Maybe that is why psilohuasca is reported to have a different feel? It might be the activation of norpsilocin!?

Neat stuff! I hope this research continues to get funding and evolves!






I see....

I didn't catch that part of the study.

That is quite interesting too though!


I've been planning on getting some caapi vine sometime in the near future, definitely looking forward to combining it with the mushrooms I've been working with for years now and seeing how different the experience is (I've only had a few relatively mild experiences with mushrooms & syrian rue so far).





-OM

.


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OfflineskOsH
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Re: Editor’s Choice Award – Best Psychedelic Chemistry/Synthesis Study of 2020 [Re: openmind]
    #27122011 - 01/02/21 01:37 PM (23 days, 16 hours ago)

A synthesis for psilocybin??? Hmm, I might need to...check their work, lol. Imagine a high yield synthesis where you can get a few grams of essentially pure psilocybin and put a little amount in gel capsules

I can just picture psilocybin precipitating out of solution and forming some crystals.


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OfflineFractal420
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Re: Editor’s Choice Award – Best Psychedelic Chemistry/Synthesis Study of 2020 [Re: skOsH]
    #27123065 - 01/03/21 02:28 AM (23 days, 3 hours ago)

First, they discovered that norpsilocin is more potent than psilocin

Quick China! Nor-4hos! Maybe even aco


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And comforting me with it's three warm and wild eyes.

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InvisibleHolybullshit
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Re: Editor’s Choice Award – Best Psychedelic Chemistry/Synthesis Study of 2020 [Re: Fractal420]
    #27124792 - 01/03/21 10:09 PM (22 days, 7 hours ago)

It's just 4-HO-NMT...Baeocystin is a prodrug for it the same way psilocybin is a prodrug for psilocin, so I don't imagine 4-aco-nmt would work any better, I guess it's just too susceptible to MAO. I wonder what 5 substituted NMT would do if taken with an MAOI, considering 5-meo-dmt's effects I might not want to know.

Quote:

A synthesis for psilocybin??? Hmm, I might need to...check their work, lol. Imagine a high yield synthesis where you can get a few grams of essentially pure psilocybin and put a little amount in gel capsules




I don't know what kind of set up you have, but its not generally something that can be done at home.


Edited by Holybullshit (01/03/21 10:15 PM)


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