• Neuroscience & Pharmacology Discussion Welcome Guest
    Posting Rules Bluelight Rules
    Recent Journal Articles Chemistry Mega-Thread
    FREE Chemistry Databases! Self-Education Guide

  • N&PD Moderators: Skorpio

Phosphorus attachment to Psilocybin chemical Structure

EarthBounded

EarthBounded

Bluelighter
Joined
Mar 2, 2013
Messages
992
Location
Right between the Solar Plexus and Heart Chakras W
I am intrigued that most substances than run American run on are Carbon, Oxygen, Hydrogen and Nitrogen based. I am actually trying to find Pharmaceuticals and Scheduled substances with Elements that are not bound to the four elements above.

This one intrigued me, C12H17N2O4P Psilocybin.

Would this Phosphorus attachment mean anything important?
Is this hitting 5-HT Receptor's differently then other popularized substances because of the Phosphorus attachment?

Thanks

EB
 
That still doesn't help me much for the answer I was looking for, however it is helpful information, it is one of the only Traditional psychedelics with an attachment that is not C,H,N,O.

I did notice psilocin was dephosphorylated I guess no one else cares much, I think there is something special about that Phosphorus attachment. call me crazzy

So does the dephosphorylation occur because of H20 content in Human body?
 
That still doesn't help me much for the answer I was looking for, however it is helpful information,
Click to expand...

I thought that does answer your question.

Would this Phosphorus attachment mean anything important?
Click to expand...

If it's being dephosphorylated into psilocin, then the chemical that gives you the effects is the psilocin (which only contains C, H, N, and O). The P part is basically useless towards the effects unless there's something I'm missing here.

EDIT: Btw, there are other compounds that aren't solely C/H/N/O. For example, the thienodiazepines (e.g. etizolam). They contain a sulfur atom.

EDIT#2: Also, it is common for there to be halides on there: Chlorine, Fluorine and Iodine.

EDIT#3: And Bromine, I'm not sure why I forgot that one...
 
Last edited:
Jackeh said:
I thought that does answer your question.



If it's being dephosphorylated into psilocin, then the chemical that gives you the effects is the psilocin (which only contains C, H, N, and O). The P part is basically useless towards the effects unless there's something I'm missing here.

EDIT: Btw, there are other compounds that aren't solely C/H/N/O. For example, the thienodiazepines (e.g. etizolam). They contain a sulfur atom.

EDIT#2: Also, it is common for there to be halides on there: Chlorine, Fluorine and Iodine.

EDIT#3: And Bromine, I'm not sure why I forgot that one...
Click to expand...


Coo thanks this is the information I am looking for/

amanitadine said:
Phosphorus houses the Gaian energy when it bonds with your pineal antennae. Duh.
Click to expand...

So it is true!!!
 
Are we 100% sure that psilocybin loses its phosphorus?

It was said that the acetylated compounds would be turned into their hydroxyls but that clearly isn't the case as they have their own unique character. Would it not be possible to have the phosphoryloxy to be active as well and and only partially converted?

And for that matter, are we 100% sure that the body doesn't phosphorylate hydroxyls in some capacity?

I know the body is capable of doing both but I don't know how that works so its a legitimate question.
 
MagickalKat777 said:
Are we 100% sure that psilocybin loses its phosphorus?
Click to expand...


The Pharmacology of Psilocybin
According to the two above-mentioned pharmacokinetic
studies in humans it was found that
after oral administration (on an empty stomach),
psilocybin is detectable in significant amounts in
the plasma within 20–40 minutes.
[...]
Psilocin appears in the plasma
after 30 minutes. A significant first-pass effect
with the vast majority of psilocybin converted
into psilocin mainly by hepatic metabolism can
be assumed.29 Another early biochemical study
showed psilocin to be the main, if not the solely
pharmacologically active substance by decreasing
the dephosphorylation of psilocybin to psilocin
using a competetive substrate (beta-glycerophosphate)
for blocking the alkaline phosphatase.30
Click to expand...

So yes it's pretty much 100% proven that psilocybin is enzymatically converted to psilocin in the liver.
 
Well yes, I get that part but doesn't injected psilocybin come on quicker than it would if it had to be turned into psilocin in order to become active?

I guess it doesn't matter at the end of the day although it does make me curious as to why we don't see phosphorloxy tryptamines in the research chemical community instead of acetyloxy.

It would be fascinating to compare the phophorloxy of, say, miprocin, with miprocin itself.
 
Psilocybin is charged at physiological pH (the phosphate group is acidic) and would not cross the blood brain barrier so would only produce peripheral effects, were it not for the rapid removal of phosphate by serum phosphatases.

It was said that the acetylated compounds would be turned into their hydroxyls but that clearly isn't the case as they have their own unique character
Click to expand...

As judged from exclusively subjective experience reports?

If you want natural heteroatom containing drugs, some sponges produce brominated tryptamines.
 
MagickalKat777 said:
Well yes, I get that part but doesn't injected psilocybin come on quicker than it would if it had to be turned into psilocin in order to become active?

I guess it doesn't matter at the end of the day although it does make me curious as to why we don't see phosphorloxy tryptamines in the research chemical community instead of acetyloxy.

It would be fascinating to compare the phophorloxy of, say, miprocin, with miprocin itself.
Click to expand...

It is more difficult to make phosphorylated compounds than acetylated. The phosphorylation reactions are messy, and the purification of polar compounds like phosphate esters is challenging. That was the reason Sasha developed the acetylated analogs
 
Help?!?! said:
Psilocybin is dephosphorylated to psilocin quite quickly once ingested.
Click to expand...

I was just having a conversation with my brothwr who happens to be am orgamic chem/pharmacology student about the proposed hydrolysis that would immediately follow dephosphorlyzation, and he didn't seem to believe it has been proven 100% that this woul be the metabolic answer and psilocybin could possibly remain unchanged through first pass metabolism. Where is your peer reviewed study proving with 100% accuracy that all higher analogies of the free phenol tryptamines are rapidly metabolized into the indolol prior to entering the BBB. It seems fishy that this concept has been circulating for so many years yet no one can provide substantial evidence to solidify it as scientific fact.
 
entheo said:
I was just having a conversation with my brothwr who happens to be am orgamic chem/pharmacology student about the proposed hydrolysis that would immediately follow dephosphorlyzation, and he didn't seem to believe it has been proven 100% that this woul be the metabolic answer and psilocybin could possibly remain unchanged through first pass metabolism. Where is your peer reviewed study proving with 100% accuracy that all higher analogies of the free phenol tryptamines are rapidly metabolized into the indolol prior to entering the BBB. It seems fishy that this concept has been circulating for so many years yet no one can provide substantial evidence to solidify it as scientific fact.
Click to expand...

Did you get a chance to read the review I linked above? I found the evidence they presented fairly convincing, but feel free to read back through their sources and see for yourself.
 
The AcO versions are definitely different than the hydroxy versions.. Someone should do the same thing as the psilocybin study but with 4-AcO-DMT to find out wtf is going on.. cause they definitely have different effects. I don't doubt psilocin and psilocybin feel identical though (except for things like come-up time etc).

Also i've noticed that when i've taken 4-AcO-DMT there is never any point during the trip where it feels like it turns into a psilocin trip (which you'd think would happen if the aco gets chopped off, even if it takes time).


Whats even more weird is i've tried to turn 4-AcO-DMT into psilocin by dissolving a little NaOH in water and mixing that with a water/4-AcO-DMT solution (when it turned dark I put some ascorbic acid in to stop the reaction). The trip from that stuff was different to both psilocin and 4-AcO-DMT (I wonder what was produced?)
 
Last edited:
two words: expectation effects

shulgin got knocked out by a cup of sugar water he thought might have sedatives in it. that doesn't mean he has the right to claim that sugar water is a powerful sedative.
 
You must log in or register to reply here.
Top