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Conditions required for Psilocybin converting into Psilocin?

Jabberwocky

Jabberwocky

Frumious Bandersnatch
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hello,

All I can find is that a thermal event has to occur to activate the breakdown of the phosphor group into the hydroxyl

Can water also cause this breakdown? I was under the impression that it could but now I am told otherwise

Isn't this why almost immediately you'll turn water blue/green if you dump some mushroom powder in (thats the psilocin decomposing) and then slowly the solution will turn even darker blue (I thought that was the psilocybin converting to psilocin then decomposing?).
 
Yeah, that makes sense. I wonder how much 4-po actually makes it into your bloodstream, or if it's all 4-ho by then?
 
Psilocin the actual active constituent, psilocybin is merely a prodrug, so I am betting that much of the phosphate moieties are chewed off by gut enzymes or simply by the pH of the gut.
 
I'm pretty sure that the change in coloration of any water you dump shroom powder into is due to substances other than psilocybin/psilocin that are present in the shrooms.
 
wait wait good sir. That cannot possibly be correct. A friend has dumped pure psilocin (synthetic) in water and has reported a bluing.

RZ, I'm talking about out of the body. Yes, I think you are correct that the gut enzymes chew the phosphor apart (converting it to psilocin).

I'm wondering what could provide the necessary requirements to convert psilocybin into psilocin OUTSIDE the body. Like hot boiling water maybe?
 
Gaian Planes said:
wait wait good sir. That cannot possibly be correct. A friend has dumped pure psilocin (synthetic) in water and has reported a bluing.
Click to expand...

I would not consider this as a specific proof for decomposition. Even synthetic psilocybin can contain traces of psilocin (depending on the route), which will yield the blue coloration.
In general is psilocybine much more stable than psilocin. See this paper for an answer: Journal of Forensic Sciences 1985, 30(1), p.247 (don't have access, otherwise I would check it myself)

- Murphy
 
Psilocybine is a phosphate ester. The hydrolysis will, therefore, be catalyzed by any acid. Driving force of the cleavage will be the energetic stabilization of the free phosphate anion in aqueous media (= citric acid or HCl in water).

Peace! - Murphy

Edit: I found some other methods, but those are rather 'complicated' in comparison to boiling acidic water. Can't go too much into detail (=synth discussion?!), but catalytic amounts of certain binuclear boron halide compounds are able to cleave the P-O-C-bond. The reaction takes place at room temperature and is effective enough to make said compounds suitable for gas maks (check the structures of VX, sarin or tabun!)
Other examples employ polyoxomolybdate clusters, Ce3+, Ce4+, La3+ and other metal ions of the d- and f-group.
 
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MurphyClox said:
I would not consider this as a specific proof for decomposition. Even synthetic psilocybin can contain traces of psilocin (depending on the route), which will yield the blue coloration.
In general is psilocybine much more stable than psilocin. See this paper for an answer: Journal of Forensic Sciences 1985, 30(1), p.247 (don't have access, otherwise I would check it myself)

- Murphy
Click to expand...

I was answering HT2's comment that he thought it was something in mushrooms OTHER than the 4-ho-DMT/4-PO-DMT that turned it blue.

thanks for the article
 
For maximum potency mushroom tea, you want to grind your mushrooms to a powder and steep in boiled distilled water and ascorbic acid. Psilocin is unstable in basic conditions.
 
^Agree with Coolio.

The oxidation needs some time. Normally such 'tea' gets consumed directly after preparation, so one must not fear to loose much material. Applying an alkaline pH would only (unnecessarily) increase the decomposition rate.

If we are talking about quantitative use of psilocybine obtained from natural sources (i.e. dried msuhrooms), I would always try to go with psilocybin and not psilocin! It was repeatedly shown that the former one gets converted in vivo into the latter one with high efficacy, so there's no need to perform the transformation in vitro before consumption.

- Murphy
 
MurphyClox said:
^Agree with Coolio.

The oxidation needs some time. Normally such 'tea' gets consumed directly after preparation, so one must not fear to loose much material. Applying an alkaline pH would only (unnecessarily) increase the decomposition rate.

If we are talking about quantitative use of psilocybine obtained from natural sources (i.e. dried msuhrooms), I would always try to go with psilocybin and not psilocin! It was repeatedly shown that the former one gets converted in vivo into the latter one with high efficacy, so there's no need to perform the transformation in vitro before consumption.

- Murphy
Click to expand...

what your saying is that there is no need to convert it before as when you drink it your body will convert it after, is how i am understanding it. but i had this tea years back and although it was strong in shroom content the cranberry tea in high concntrations which was really tangy and bitter might have been responsible for oe of the fastest come ups in history-15 minutes and i was spinning round like a rollercoaster. because it hit so quick the high was way more intense. seems like a rapid come up leads to mad super strong trips-in fact the ones made with acidic fruit tea have been top notch joy fests way more disorientating way more visual
 
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MurphyClox said:
^Agree with Coolio.

The oxidation needs some time. Normally such 'tea' gets consumed directly after preparation, so one must not fear to loose much material. Applying an alkaline pH would only (unnecessarily) increase the decomposition rate.

If we are talking about quantitative use of psilocybine obtained from natural sources (i.e. dried msuhrooms), I would always try to go with psilocybin and not psilocin! It was repeatedly shown that the former one gets converted in vivo into the latter one with high efficacy, so there's no need to perform the transformation in vitro before consumption.

- Murphy
Click to expand...

but who has shown this? MY understanding is it is a theory. Lots of us have had the chance to sample a wide smorgasbord of tryptamines. We have generally found substantial difference in the phenomenal experience of mushrooms, 4-HO-DMT, 4-AcO-DMT compared to each other.

Could the 4-PO-DMT convert in vivo to 4-HO-DMT yet the 4-aco-DMT does not and somehow gets across the BBB?
 
Gaian Planes said:
but who has shown this? MY understanding is it is a theory. Lots of us have had the chance to sample a wide smorgasbord of tryptamines. We have generally found substantial difference in the phenomenal experience of mushrooms, 4-HO-DMT, 4-AcO-DMT compared to each other.

Could the 4-PO-DMT convert in vivo to 4-HO-DMT yet the 4-aco-DMT does not and somehow gets across the BBB?
Click to expand...

I'll look up the references but I remember several publctions who showed practically quantitative conversion of psilocybin in vivo, and not just quantitative but also fast conversion!

The "substantial difference" between the mentioned compounds resp. preparations could be explain by other means IMO:

- Acetyl esters get cleaved by other enzymes than phosphate esters. I would think that the activity of the respective enzymes can indeed lead to different results, even if one used in both experiments the same molar amount of DMT-derivate.

- Also I wonder if it isn't possible that non-deacetylized 4-AcO-DMT could get deactivated (MAO) before it gets deacetylated. That would make comparison of the same starting amount a bit difficult. But this point is more a bit of a speculation...

- I think that while psilocybin does not cross the BBB (the phosphate group is charged!), 4-AcO-DMT does, as does psilocin. That makes up a different pharmacokinetic, don't ya think?

- How could you ensure the same dose when trying out mushrooms vs. pure psilocybine vs. pure psilocin?! Mushrooms are a complex composition of at least 4 psychoactive tryptamines (in addition to the already mentioned ones: baeocystine and the nor-congener), in some way bound to a cellular matrix. Even if some of them are not as active as the "standard" (i.e. psilocybin), they may modulate the whole experience. Plz do also consider that when comparing a pure crystalline substance with such a complex natural product, one must not forget the liberation of the respective substance(s) from the plant/mushroom material. Was it powdered? Or just chewed into pieces? Was it dried before consumption or still wet or maybe fresh mushrooms?

This all makes a qualitative difference for the resulting trip, the main difference probably being different speed of upcoming of the effects. But, as elaborated above, we do also encounter differences in the pharmacokinetics (think: LADME!).

YO! Murphy
 
Ok, there are some studies done with liver homogenates, as well as with living mice, IIRC. But I think it makes more sense to consider this publication performed in humans instead:

"Determination of psilocin and 4-hydroxyindole-3-acetic acid in plasma by HPLC-ECD and pharmacokinetic profiles of oral and intravenous psilocybin in man."
F. Hasler et al.
Pharmaceutica Acta Helvetiae 1997, 72(3), p.175

Abstract

In order to investigate the pharmacokinetic properties of psilocybin (PY), the main psychoactive compd. of Psilocybe mushrooms, high performance liq. chromatog. procedures with column-switching coupled with electrochem. detection (HPLC-ECD) for reliable quant. detn. of the PY metabolites psilocin (PI) and 4-hydroxyindole-3-acetic acid (4HIAA) in human plasma were established. Sample work-up includes protection of the highly unstable phenolic analytes with ascorbic acid, freeze-drying and in-vitro microdialysis. The data of two controlled clin. studies with healthy volunteers are presented. The subjects (N = 6 for both studies) received single oral PY doses of 0.2240+/-02 mg/kg b.wt. (10-20 mg) and i.v. doses of 1 mg PY, resp. Peak plasma levels of PI after oral administration of PY were measured after 105+/-37 min showing an av. concn. of 8.2+/-2.8 ng PI/mL plasma. 4HIAA peak concns. of 150+/-61 ng/mL plasma were found 113+/-41 min after ingestion of PY. After i.v. administration, a mean PI max. plasma concn. of 12.9+/-5.6 ng/mL plasma was found 1.91.0 min after injection. The max. plasma levels appearing within a very short period indicate a rapid dephosphorylation of PY also when administered systemically; 4HIAA was not detected after 1 mg of i.v. PY. Ests. for the abs. bioavailability of PI after oral administration of PY were 52.720% (N = 3).
Click to expand...

Sounds convincing to. The Vollenweider-group got quite a good reputation when it comes to psiloccybin-pharmacology and I would, therefore, trust this date.

Peace! - Murphy
 
Gaian Planes said:
wait wait good sir. That cannot possibly be correct. A friend has dumped pure psilocin (synthetic) in water and has reported a bluing.

RZ, I'm talking about out of the body. Yes, I think you are correct that the gut enzymes chew the phosphor apart (converting it to psilocin).

I'm wondering what could provide the necessary requirements to convert psilocybin into psilocin OUTSIDE the body. Like hot boiling water maybe?
Click to expand...

Well..if it is in an acid environment it can turn into psilocin..acid like honey or chocolate ;)
 
^ due to hydrolysis? I have been interested in the conversion, because when I take mushrooms, i do the so-called "lemon trick". Basically about 2-3 fl. oz of cold water, and 1-2 lemons worth of juice squeezed into the cup of water. The mushrooms are finely shredded by hand or ground up as much as possible. They are placed in the lemon/water solution for about 20-30 mins. Then the liquid/Shroom mix is taken as a shot or two. The shroom peices become soaked In the solution making it easier to swallow all at once, liquid and shroom peices. I have done it about 4 times of the 20-30 shrooms trips and it is much faster comeup, more intense/gram shroom used, and lasts about 2/3-3/4 as long as just eating the mushies alone. I have long been wondering why this method is so successful. It also avoids nausea as long as you aren't sensitive to the lemon juice acidity.
 
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