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Offlineuneasyone
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psilocin vs psilocin salts
    #2931576 - 07/27/04 08:07 AM (12 years, 4 months ago)

does anyone know which is more stable the freebase or the hcl salt?


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Edited by uneasyone (07/27/04 12:04 PM)


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Offlineuneasyone
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Re: psilocin vs psilocin hcl [Re: uneasyone]
    #2931595 - 07/27/04 08:29 AM (12 years, 4 months ago)

also i would like to know if ascorbic acid dissolved in water or better yet 70% ethanol then added to the nonpolar phase of the a-b extraction would be enough to strip the psilocin away from the ether and create a salt maybe psilocin ascorbate? would that be more stable than the hcl salt or the freebase?


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Edited by uneasyone (07/27/04 11:38 AM)


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Invisiblemicro
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Re: psilocin vs psilocin hcl [Re: uneasyone]
    #2933590 - 07/27/04 07:18 PM (12 years, 4 months ago)

The salt would be the more stable form. You don't want to add alcohol because it is miscible with the np. I don't see why the base + ascorbic acid wouldn't undergo a reaction, but I've never tested it. I don't know how stable that would be, but there's no particular reason it would be unstable. The only reason a salt is more stable is because the amine site (which is the most basic part) is blocked from attack by an electrophile. If it reacted with an acid it's the salt of that acid -- vinegar would yeild the acetate salt and yes -- ascorbic acid yeilds an ascorbate.

JMO

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Offlineuneasyone
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Re: psilocin vs psilocin hcl [Re: micro]
    #2933630 - 07/27/04 07:32 PM (12 years, 4 months ago)

do you think the acetate salt would more stable than the hcl or ascorbate salts? the reason i was thinking about adding an excess of ascorbic acid was because it is supposed to be an antioxidant (which would help in preserving the extract) plus it's just vitamin c which would be a pretty harmless cutting agent. i don't know if this would be the best route though so i need some advice from you chemistry guys out there


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Offlineuneasyone
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Re: psilocin vs psilocin hcl [Re: uneasyone]
    #2934264 - 07/27/04 10:48 PM (12 years, 4 months ago)

oh yeah do any of you know of another polar solvent that would be quicker to evaporate than water, dissolve ascorbic acid, would not mix with the diethyl ether, and most importantly not kill the magic or another nonpolar solvent besides diethyl ether that would dissolve psilocin freebase and that would not mix with ethanol


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anything i might say is just something i heard from the voices in my head
uneasy1


Edited by uneasyone (07/28/04 08:35 AM)


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Invisibletrade_om
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Re: psilocin vs psilocin hcl [Re: uneasyone]
    #2935491 - 07/28/04 06:10 AM (12 years, 4 months ago)

HA!
Psilocin as a rule is not veyr stable, as are all 4-hydroxy substituted indoles. A salt would be more stable then the freebase form. The free base form will decompose veyr rapidly. Any 4-subtituted indole (tryptamine) is very unstable at basic conditions.


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OfflineChuangTzu
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Re: psilocin vs psilocin hcl [Re: uneasyone]
    #2936347 - 07/28/04 03:17 PM (12 years, 4 months ago)

Ethanol mixes with all common solvents according to:
Solvent miscibility chart .
Assuming you have an ethereal solution of psilocin and want to obtain its salt, you need to dissolve that stuff in the most non-polar stuff possible (since in the end you will be trying to get the salt out of it and you may have to use a not-very-ideal polar solvent since ethanol is out of the question and we want to minimize the amount of water involved..)  This can be done by crystallizing from the ether and then redissolving in the chosen solvent.  Psilocin is soluble in a chloroform/heptane mix (1:3) Extraction Method for the Isolation and Identification of Psilocin - [www.rhodium.ws].  Is this non-polar enough?  I don't know.  You'd have the best results if you had some data on relative solubilities of the salt you are trying to obtain but this probably isn't available.  Maybe you can collect some after you get it :smile:

From there, you can try to form the salt in an acidic methanol phase and then crystallize  since there will be relatively little water getting in your way. But again, I don't know if the salt will be more soluble in the polar but light methanol or the heavier heptane.
If you have access to more exotic solvents, then perhaps you could try something a bit more crafty. 
Maybe it's just easier to get some psilocin crystals and store them in a cool, dark, dry place.  Who knows what the gain in stability would be anyway...

After all that, I just found the following:  Synthesis of Psilocybin & Psilocin  - [www.rhodium.ws]  which indicates that the lithium salt of psilocin is much more stable than the free base and that it can be prepared from tetrahydrofuran (if you have access to it...)

Hope that helps.


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Offlineuneasyone
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Re: psilocin vs psilocin hcl [Re: ChuangTzu]
    #2945528 - 07/30/04 05:49 PM (12 years, 4 months ago)

i think it did thanks


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Invisiblemicro
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Re: psilocin vs psilocin hcl [Re: ChuangTzu]
    #2950248 - 07/31/04 11:59 PM (12 years, 4 months ago)

Quote:

From there, you can try to form the salt in an acidic methanol phase and then crystallize since there will be relatively little water getting in your way. But again, I don't know if the salt will be more soluble in the polar but light methanol or the heavier heptane.




What is acidic methanol, and how do you seperate alcohol and heptane? Just curious.

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Offlineuneasyone
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Re: psilocin vs psilocin hcl [Re: micro]
    #2951193 - 08/01/04 10:28 AM (12 years, 4 months ago)

according to that link he posted micro heptane and methanol are not miscable


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OfflineChuangTzu
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Re: psilocin vs psilocin hcl [Re: micro]
    #2954708 - 08/02/04 02:52 AM (12 years, 4 months ago)

Acidic methanol is simply methanol to which an acid has been added. And, like uneasyone said, methanol and heptane don't mix so you just let them sit (they form layers like oil and water) then siphon one off the other. Or use a seperatory funnel.


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Re: psilocin vs psilocin hcl [Re: ChuangTzu]
    #2960254 - 08/03/04 03:20 PM (12 years, 4 months ago)

Quote:

Acidic methanol is simply methanol to which an acid has been added.




No -- there is no such thing as "acidic methanol."  You could mix an aqueous solution of HCl and methanol, but it is just that -- you still need water.  Methanol does not dissociate the same way as water, so the pH scale does not apply to it.

Quote:

And, like uneasyone said, methanol and heptane don't mix




I stand corrected.  I was looking at ethanol :wink:

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OfflineChuangTzu
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Re: psilocin vs psilocin hcl [Re: micro]
    #2960791 - 08/03/04 05:26 PM (12 years, 4 months ago)

Quote:

Methanol does not dissociate the same way as water, so the pH scale does not apply to it.




Methanol usually contains some percentage water, unless freshly distilled, so that is not a problem. Also if your acid is HCl (which it would be if preparing the hydrochloride salt) it will, unless in gas form, carry its own water with it. Lastly, you can dissolve an acid directly in pure methanol, and it can be considered acidic relative to neutral methanol, that is, methanol that doesn't have acid dissolved in it -- no need for a pH scale. The acid will dissociate and protonate the OH but achievable concentrations will be much lower than they would be in water with the same acid.

Quote:

No -- there is no such thing as "acidic methanol."




Have you seen how many abstracts you can find by simply searching google for the term "acidic methanol?"


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Offlineuneasyone
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Re: psilocin vs psilocin hcl [Re: ChuangTzu]
    #2961009 - 08/03/04 06:18 PM (12 years, 4 months ago)

I've got three questions. 1. do you guys think the hcl salt would be more stable than the acetate or ascorbate salts? 2. just how nonpolar is heptane more or less than ether? 3. if i were to gas the nonpolar with hcl precipitate the salt then add methanol stir and separate layers then add an excess of ascorbic acid to the methanol phase then evaporate. would the ascorbic acid acid turn the hcl salt into the ascorbate salt or would i have a mixture of the hcl salt and vitamin c?


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Offlineuneasyone
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Re: psilocin vs psilocin hcl [Re: uneasyone]
    #2961534 - 08/03/04 09:13 PM (12 years, 4 months ago)

i just looked at a msds sheet for vm&p naptha it said contains n-heptane would this be sufficent for extraction instead of di-ethyl ether?


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Re: psilocin vs psilocin hcl [Re: ChuangTzu]
    #2974155 - 08/07/04 01:28 AM (12 years, 3 months ago)

Well, first of all, the salt is not soluble in heptane. Secondly, where is your evidence that the reaction will even take place in an alcohol? Third of all, what OH is being "protinated?" Fourth of all, you have no idea what you're talking about, so please go away.

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OfflineChuangTzu
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Re: psilocin vs psilocin hcl [Re: micro] * 1
    #2977502 - 08/08/04 06:07 AM (12 years, 3 months ago)

Who ever said anything about the salt being soluble in heptane? That would be ridiculous.

If you can dissolve an acid with a high enough pKa in the alcohol, the salt will be formed. It just can't be too high or the methanol will start substituting itself and forming ethers. Free bases are just that, basic, so they're pretty easy to turn into salts. So if it's possible to dissolve in the methanol something acidic enough to form the salt but not acidic enough that an appreciable amount of methanol undergoes reaction, the procedure should work. Ascorbic acid should fulfill this criteria.

The OH I was talking about is the hydroxyl group of the methanol, obviously. To protonate is a real verb, it doesn't need quotes.

You're right, I learned absolutely nothing from the portion of my life during which I spent 80% of my waking hours in the lab doing natural product isolation. Or the years of sitting in organic chemistry classes. Or my time working in a chemistry lab. You definitely know a lot more so I'll just step aside and let you do all the thinking.


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OfflineNeurogenesis
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Re: psilocin vs psilocin hcl [Re: ChuangTzu]
    #13729644 - 01/04/11 03:57 PM (5 years, 10 months ago)

Quote:

ChuangTzu said:
"Acidic methanol is simply methanol to which an acid has been added"

I understand this thread is extremely old, but this is crucial.

If you add and acid with a Pka < ~15, the hydroxyl group will become protonated, and leave as H20. Depending on the anion group of the acid, you can get many different products. Under NO circumstances use HCl as your acid for this! Your product will be methyl chloride which will flash immediately and violently, not to mention poison you. This kind of chemistry should be left to the chemists and chemical engineers.

I felt that this was important enough to post ... hope nobody tried it


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Re: psilocin vs psilocin hcl [Re: Neurogenesis]
    #13732803 - 01/05/11 01:46 AM (5 years, 10 months ago)

HCl in methanol is nothing to worry about (for that reason). It is quite commonly used and one can even buy it pre-prepared. I can explain why you will not get CH3Cl in a PM if you want, it is highly likely off topic :crazy:


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OfflineRogerRabbitM
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Re: psilocin vs psilocin salts [Re: uneasyone]
    #13734121 - 01/05/11 01:46 AM (5 years, 10 months ago)

This thread has been closed.

Reason:
This thread was off topic six years ago when it was current.  I must have missed it back then.
RR


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