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Registered: 11/09/04
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Sam, A stab at the stomach acid question....
    #3345122 - 11/11/04 03:54 AM (11 years, 11 months ago)

Hey sam and others, I have a pretty good idea of what stomach acid does to psilocin and psilocybin. in the case of psilocin, there is a hydroxyl group coming off the benzene ring. Stomach acid has a very low PH, sometimes as low as two or three. This means lots of protons floating around. Whicn means taht the hydroxyl group -OH will stay protonated in the stomach since it is surrounded by a sea of protons. This molecule is highly non-polar in this form and can pass through membranous structures. It may pass through passively here but this is highly unlikely since its such a large molecule. Likely it will tend to be passed down into the small intestine. Here, the environment is more basic, and the hydroxyl group will become deprotonated giveing psilocin a full negative charge. This makes psilocin an enolate ion and very polar. It can now cross over into the blood stream via some polar transmembrane protien. It is very unlikely that the polar form of the molecule simply diffuses through the membrane into the bloodstream because it cannot in its full and negative glorious charge span the non-polar membrane. "LIKE DISSOLVES LIKE". And besides its too big. If it does diffuse through the membrane however on its own, then its more likely that in the stomach is the sight of diffusion as the molecule is non-polar here.
It is liekly as well that in the stomach, psilocybin is converted to psilocin by dephosphorylation and protonation of the 5-terminus on the benzene ring. So it is likly that psilocybin can not be utilized at all by the seratonin and dopamine receptors in the brain, but must be in the form of psilocin. This is ok, since the body has a way of converting to psilocin. It would be interesting and I would think there would be a strong correlation between psilocybin content and time of peak activity. In otherwords, dephosphorylation takes time. I would be willing to put money on it, if the psilocybin/ psilocin ratio is high (high psilocybin content, low psilocin content) in a batch, the longer they take to start working but also the longer the trip. If the psilocybin/psilocin ratio is low (low psilocybin, high psilocin) then the trip takes effect faster, because the body doesnt have to dephosphorylate and protonate the molecule, but i bet it wears off faster. This is all speculative but based on real biochemistry!!! Its my major, I should be able to at least make a logical stab at it.

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Registered: 10/25/04
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Re: Sam, A stab at the stomach acid question.... [Re: thashaman]
    #3345335 - 11/11/04 05:03 AM (11 years, 11 months ago)

u've got them book smarts learning  :muppet:


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Re: Sam, A stab at the stomach acid question.... [Re: thashaman]
    #3347730 - 11/11/04 06:16 PM (11 years, 11 months ago)

My trips always come on faster when I eat fresh mushrooms (higher psilocin content) than when I eat dry mushrooms so this makes sense even if I don't understand most of it.

"Of all tyrannies, a tyranny exercised for the good of its victims may be the most oppressive. It may be better to live under robber barons than under omnipotent moral busybodies. The robber baron's cruelty may sometimes sleep, his cupidity may at some point be satiated; but those who torment us for our own good will torment us without end, for they do so with the approval of their own conscience." - C.S. Lewis

"I would rather be exposed to the inconveniencies attending too much liberty than to those attending too small a degree of it." - Thomas Jefferson

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Re: Sam, A stab at the stomach acid question.... [Re: thashaman]
    #3348944 - 11/11/04 11:15 PM (11 years, 11 months ago)

Great job reasoning that out.... :thumbup:

"..all those molecules thrashing their kinky little tails, hot for destiny and the street."  Gibson

Nuke baby seals for Jesus!

(This has been a +1 production.)

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Re: Sam, A stab at the stomach acid question.... [Re: thashaman]
    #3350666 - 11/12/04 10:51 AM (11 years, 11 months ago)

i always thought that shroom-kool-aid hit you faster (waaay faster) because the compunds didn't have to be mechanically extracted from the fruitbody by your stomach/intestines. now, i'm wondering if the low pH (from ascorbic acid) helps speed things along as well.

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