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 Pinback
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 Re: Sublingual usage of psilocybin extraction precipitates [Re: fastfred]
#6052679 - 09/12/06 08:12 AM (5 years, 8 months ago) |
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Hello fastfred,
your structure breaks aromaticity of the benzyl moiety because one of the carbons no longer has a p orbital where electrons can roam. In an orto- or para-quinoid structure, aromaticity would be conserved because all carbon atoms have a p orbital, and Hückel's rule is also fulfilled (reality is a bit more complex though).
Typically, fenols give p-quinones when oxidized, unless the para position is blocked. In this case, orto oxidation is observed, giving the o-quinoid structure. Oxidative coupling of two or more aromatic moieties is also commonly observed, giving a complex mixture of compounds.
Serotonin (5-hydroxytryptamine) can be oxidized to give the 4,5-dione. Maybe this is why a o-quinoid structure was proposed in that paper.
Electrolytic oxidation of 4-hydroxyindole leads not to a quinoid structure, but to oligomerization (the compound was described as "greenish-black", but I don't think one can draw any conclusions from that).
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fastfred
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Re: Sublingual usage of psilocybin extraction precipitates [Re: Pinback]
#6053651 - 09/12/06 01:25 PM (5 years, 8 months ago) |
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Thanks for the discussion Pinback. It's been quite a while since I've worried about Huckel's rule.
It's true that the double bond eliminates one of the free p orbitals on the benzene ring that is required for aromaticity. But aromaticity is not a requirement for producing color. The simple presence of conjugated bonds is more indicative of color production than aromaticity.
Maybe I'm wrong, but I think the conjugated bonds look like they could produce a blue color. Even without conjugated bonds there still could be a color produced.
Electronic configuration and color theory are not strong points of mine, so until this post I hadn't even really considered them. I proposed a few o-quinoid structures in a post years ago, but I couldn't seem to figure out anything that looked plausible.
My structure accounts for psilocin's instability in alkaline solutions and that hydroxyl group simply looks the most vulnerable to oxidation to me.
O=C- groups are good chromophores so I think it's definitely possible that my structure is compatible with the observed blue color. Nitro groups are also good chromophores, but if the structure was an oxidized indole N type, then I would think that it would be more likely to be unstable in acidic solution rather than in basic solution, which doesn't fit.
Anyhow, I would love to see what structures you propose. Could you draw up a few to illustrate what you mean?
As far as I know I'm the only person to have proposed an actual structure for the oxidation product. The only other suggestion I've seen is the rather vague "possibly of an O-quinoid structure," in the literature.
Here is my first stabs at a structure that I posted back in 04.
http://www.shroomery.org/forums/showflat.php?Cat=0&Board=Forum4&Number=3128800
Kind of sucks that the thread is now dead. It must have simply expired.
Hmm... Looking back I see you did post something on the subject. Looking in my old post it seems like electrooxidation of seritonin produces the structure corresponding to the structure I've proposed.
I'm fairly satisfied with my structure, but I'd love to hear some discussion on it and/or proposal of alternate structures.
-FF
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Pinback
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Re: Sublingual usage of psilocybin extraction precipitates [Re: fastfred]
#6056504 - 09/13/06 08:05 AM (5 years, 8 months ago) |
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True, I should not have mentioned color as color prediction is extremely complex. However, the structure you are proposing is still not an oxidized version of psilocin, but a (highly unfavoured) tautomer. It is only a transfer of the proton from the oxygen to the 7-position (bottom carbon on the drawing). While you could say that the carbon binding to oxygen is oxidized, the bottom one is reduced.
Here are some ideas of other structures:
Dimerization (or oligomerization) could also be done in other positions, for example on the oxygen and 5-position.
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 TrancedShroom
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Re: Sublingual usage of psilocybin extraction precipitates [Re: Pinback]
#6061122 - 09/14/06 01:28 PM (5 years, 8 months ago) |
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^This guy knows his science.
Sounds like he has made LSD before............
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coctyle
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Re: Sublingual usage of psilocybin extraction precipitates [Re: wiggles]
#6061887 - 09/14/06 04:41 PM (5 years, 8 months ago) |
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So, did anyone actually read the post by geko127? This gives the answer to the original question of how to make a pure psilicin crystal extract!
To summarize, dilute acetic acid, aka vinegar, is an ideal solvent for both psilicybe and psilicin. Heating the acidic solution will dephosphorylize the psilicybe, leaving pure psilicin. Of course, I'm not sure if I would want to do that as it would be most reactive in that form. The solution can then be basified, which will precipitate salts and the "free-base" psilicin. This can then be dissolved by a non-polar solvent, everything else filtered and discarded, and the n-p solvent evaporated to leave a pure crystal.
You could stop at the vinegar solution, which can be evaporated to give something potent enough that you can drink a small quantity of it (a few ml maybe) and have a good effect. But from what I understand, it won't keep long. The acid will destroy the psilicin eventually.
Anything with water, even Everclear, will dissolve the enzymes that convert psilicybe to psilicin, and dephosphorylization will occur in vitro. Everything I have read tells me that psilicybe is not soluable in ethanol, but psilicin is, so the ethanol only holds the stuff that has been converted by the phophatase enzyme in the solution. The crystals in an everclear solution, I believe, are psilicybe crystals that precipitate out from the water as the solution cools (presuming you are doing Everclear ext at elevated T). It makes sense that the solution with crystals in it is stil potent even if the crystals themselves are not consumed for two reasons. First, the existance of the crystals means that the water in the solution is saturated with psilicybe Second, crystals may be a sign that the supply of phosphatase enzyme in the solution has been completely exhausted, thus meaning that there is a lot of psilicin dissolved in the ethanol.
I still agree that storing of a pure crystal would be a problem. Do we have any pharmacists here. How do the active ingredients in pressed tablets stay potent? I'm sure some OTC and prescrip meds are subject to oxidation, but I always assumed that they were pressed with some additive that resists the absorbtion of oxygen beyond the surface. Or maybe the standard fillers and binders create a good enough barrier.
Caplets would be a diffeent thing. Perhaps dissolve the powder in as small amount of honey as possible, and fill the caps with the honey? For an inert environment, how about you get a box that can be sealed, but install a small valve in the top that will let air out, but not let air in. This could be as simple as a tube that curves down into a glass of water. Air could bubble out through the water, but O2 could not get in. Then put some dry ice in the box and seal it up. As the dry ice evaporates, the gas will push out the air. After awhile I think the chamber would be clear of O2. Of course you would need to put everything you need inside in advance, or have a pass-through chamber that would allow you to put stuff in and only transfer a small amount of air with.
Check this out: http://www.cognitiveliberty.org/shulgin/adsarchive/extraction.htm
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geko127
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Re: Sublingual usage of psilocybin extraction precipitates [Re: coctyle]
#6063663 - 09/15/06 05:21 AM (5 years, 8 months ago) |
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And anyway, Why the fuck would ya want some bitter tasting tablet or powder or some shit under ya tung, When ya can just have a shot glass with the extraction liqior in it, YUK AAAAWWWWW , fuck that, its bad enough as it is.
Simple, Thats 30ml.
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LIFE IS A BITCH, AND THEN YOU MARRY ONE.
BUT SUCH IS LIFE !
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shymanta
Mad Scientist
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Re: Sublingual usage of psilocybin extraction precipitates [Re: wiggles]
#6066814 - 09/16/06 12:12 AM (5 years, 8 months ago) |
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In response to ridding a chamber of O2, if that is still an issue, I once put an alcohol lamp into a glove box that had been sprayed with Lysol. Yeah, I know.  Bad idea. It never ignited until I had some Lysol on the glove use to light the lamp. A poof and warm gloves was all that ever happened. But the point is the lamp could not be re-lit. No O2. Tamadragon suggested something like this.
On another thought, I've heard of people using Everclear to extract this or that and use it under the tung. They say its hell but its not poisonous. Maybe extract in Everclear to a one drop dose and mix with two drop of water before dosing.
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Quake3
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Re: Sublingual usage of psilocybin extraction precipitates [Re: shymanta]
#6071908 - 09/17/06 06:44 PM (5 years, 8 months ago) |
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I don't know why you guys are making this so complex. It sounds like you're attempting a total synthesis of Psilocybin. Extracting the alkaloids is trivial for most substances.
Extracting alkaloids from Psilocybe: http://leda.lycaeum.org/?ID=13433
Kitchen chemistry: http://leda.lycaeum.org/?ID=13378
It usually doesn't involve anything more than mixing things together and straining. You don't need to know anything more than how to read.
There are pictorials around if you search Google.
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shymanta
Mad Scientist
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Re: Sublingual usage of psilocybin extraction precipitates [Re: Quake3]
#6072152 - 09/17/06 07:48 PM (5 years, 8 months ago) |
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Did you really just tell everyone in this thread they're making it too hard, that its really quite easy and at the same time post two links to rather complex extraction methods?
Just to be clear...
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wiggles
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Re: Sublingual usage of psilocybin extraction precipitates [Re: shymanta]
#6072684 - 09/17/06 10:48 PM (5 years, 8 months ago) |
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The reason i want to avoid using an aqueous everclear solution is simple. If you've ever used an everclear solution before without all of the everclear extracted, it burns like 10 bitches on a bitch pole of bitchery when you apply it sublingually.
I've used multiple drops of a thc tincture prepared with everclear sublingually, and managed to keep it there for about 45 seconds. That portion of my bottom jaw had a rough spot on it for close to a week (it seemed like a chemical burn), not to mention it put me through mindbending pain to keep it there.
It would be much, MUCH easier if you could simply take a precipitate and sprinkle it sublingually.
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You can turn your back on a person, but never turn your back on a drug, especially when its waving a razor sharp hunting knife in your eye.
Hunter S. Thompson
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shymanta
Mad Scientist
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Posts: 904
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Re: Sublingual usage of psilocybin extraction precipitates [Re: wiggles]
#6072756 - 09/17/06 11:08 PM (5 years, 8 months ago) |
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Hmm... I just read the crystal myth thread. http://www.shroomery.org/forums/showflat.php/Cat/0/Number/6033769/an/0/page/0 Which suggests that the precipitates wouldn't do anything anyway since they seem to be just carbohydrates. But I think they would if you evaporated all the alcohol away. This would deposit the actives on the precipitates and they would work. That's how the THE CRYSTALS OF THE GODS - PF Extraction describes it. http://www.fanaticus.com/mycoalki.htm It assumes the crystals are active but that doesn't matter as long as you don't discard the liqueur. This might work sublingual, I think.
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Feelers
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Re: Sublingual usage of psilocybin extraction precipitates [Re: shymanta]
#6072777 - 09/17/06 11:15 PM (5 years, 8 months ago) |
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Quote:
The reason i want to avoid using an aqueous everclear solution is simple. If you've ever used an everclear solution before without all of the everclear extracted, it burns like 10 bitches on a bitch pole of bitchery when you apply it sublingually
It's not that bad - I "procured" some 95% ethanol from my lab and doing shots of that was a very quick and easy way to get drunk. 
My best was a 350ml glass full, and in ten secs it's like downing 5 or six beers I think. Sometimes it would leave you with a dry mouth but nothing unmanagable.
And also why is it such a problem to boil off the alcohol? Surely left on a window sill for a day or two should make it all evapourate.
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TheBotanist
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Re: Sublingual usage of psilocybin extraction precipitates [Re: Pinback]
#6098791 - 09/25/06 01:37 PM (5 years, 7 months ago) |
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Quote:
Pinback said:
All this talk about getting rid of the oxygen also ignores the fact that the oxygen that gets oxidized is already present in the psilocybin. All that's needed is a base (electron donor) to oxidize the psilocin.
I think you are confusing the concepts. A base (in the Lewis sense) is a chemical species that can form a bond by donating an electron pair. It is not closely related to redox reactions. Also, if a species were to lose a single electron to the psilocin, the psilocin would be reduced, not oxidized.
your wrong their. Oxidation involves loss of electrons, whereas reduction involves gain of electrons. An easy acronym is OIL RIG. I just had to clear this up.
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Pinback
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Re: Sublingual usage of psilocybin extraction precipitates [Re: TheBotanist]
#6101192 - 09/25/06 11:08 PM (5 years, 7 months ago) |
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your wrong their. Oxidation involves loss of electrons, whereas reduction involves gain of electrons. An easy acronym is OIL RIG. I just had to clear this up.
Your definition is right, but your conclusion is not.
If species X loses an electron to psilocin, then
X is oxidized (has lost an electron) and
psilocin is reduced (has gained an electron).
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shirley knott
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Re: Sublingual usage of psilocybin extraction precipitates [Re: TheBotanist]
#6102510 - 09/26/06 09:05 AM (5 years, 7 months ago) |
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meh
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