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Mushrooms / Psilocin and Psilocybin Workthread Options
 
endlessness
#1 Posted : 10/23/2012 4:57:20 PM

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Feel free to add any information you might find on different mushrooms, their habitats/geographical distribution, traditional uses, identification, cultivation, extraction, analysis etc.

I'll start:

(info below from Trout's Notes on Some Simple Tryptamines)

Psilocybin

Free base:
Stable compound. Colorless crystals. Hofmann 1971
pH 5.2 (in 50% EtOH) Merck 9th
More stable than psilocin. Shulgin & Shulgin !997
mp 175-180° Repke & leslie 1977
mp 185-195° (from boiling methanol) Ott 1996
mp 185-195° (from methanol) Picker & Rickards 1970
(Also in Perkal 1981)
rnp 185- 195° (dec.) (white crystals) Clarke 's 1986
mp 190° Mantle & Waight 1969
mp 218-228 (colorless needles from n-butanol saturated with water) Koike et al. 1981
mp 219-222° (6-angled plates from methanol) Troxler et at. 1959
mp 200-210° (dec.) Bellman 1968
mp 204-210° (rod-shaped crystals from methanol; after 10days in a freezer) [co-mp with reference material was 205-210°Pleased Leung et al 1965
mp 220-228° (crystals from boiling water) Ott 1996

Solubility:
White crystals '~fairly soluble in ·water" . Hofmann 1959
Readily water soluble. Hofmann 1971
Forms crystals from boiling methanol or boiling water;
Soluble in boiling water (1 :20),
Slightly soluble in boiling methanol {1 : 120);
Slightly soluble ("difficultly"Pleased in ethanol;
Practically insoluble in chloroform or benzene.
Merck 9'th
Practically insoluble in ethanol, chloroform or benzene. Hofmann
et al. 1958
"practically insoluble in the usual organic solvents'' Hofmann
1959
Insoluble in ether. Picker & Rickards 1970
Soluble 1:20 in boiling water; 1: 120 boiling ethanol. Pcrkall981
Many workers have successfully used cold or ,room temperature methanol for isolations.
Soluble in dilute acetic acid (as acetate) Clarke's 1986
Soluble in dilute acids
Soluble in di lute bases
Insoluble in butyl chloride
Lee 1985
Base is amphoteric. Hofmann 1959 (Soluble in acids & bases; can 't extract from either with organic solvent)

Hydrochloride:
Insoluble in acetone; insoluble petroleum ether; soluble in hot
ethanol; poorly soluble in cold ethanol. Isolate·d via crystal-
lization with cold from ethanol. Anon 2003


Unlike psilocin. wlllch is readily oxidi:ted, psilocybin is stable
enough to be detectable for many years in herbariums (Dried
psilocybin shrooms appear to remain usable for around 9 years
or sometimes longer if kept in proper storage; sbrooms wruch
contain psilocin o ften appear to rapidly degrade in storage)



Isolation:
Hatfield el a/. 1978
Hofmann e1 a/. 1958 & 1959
Koike eta/. 1981 (Using preparative TLC followed by a column of cellulose & also using an anion exchange resin.)
Leung et at. 1965 (via LC on a column of cellulose.)
Picker & Rickards 1970 (LC on column of cell ulose.)
Crude isolation from initial extract using cellulose column with Butanol saturated with water as elutant. Separated from baeocystin using silica gel column with n-propanol-5 % ammonium hydroxide (5: 1) as elutant. Leung & Paul1967

"Optimum extraction"
Homogenizing 2 minutes in 30 ml of methanol per gram of powdered pshrooms recovered all psilocybin . Perkal 1981
Repke & Leslie 1977 used n-propanol-5% ammonium hydroxide (5:2) on silica gel for preparative tlc. Elution was with methanol containing 5% aqueous ammonia.

Many workers have used methanol successfully. It appears that it works fine either cold or at room temperature.

One trend noted in the literature though, after the extraction is complete, the faster it can be processed to pure or concentrated material (with the minimal heat exposure possible) the higher the potential yield appears to be. This is likely due to degradation despite psilocybin being a fairly stable compound.

Butanol or ethanol combined with acetic acid and water also appears to be ao excellent extraction solvent.
Wurst eta/. 1984 made the statement that "Boiling ojji·uit bodies in water results in a quantitative extraction of psilocybin. The subsequent extraction ... with methanol did nor yield even traces." but provided no further detail.

For direct consumption, the simple extraction of chopped or shredded mushrooms with water and lime juice (or citric acid) works extremely well (color of the resulting solution is tawny not blue) Heat & cooking time should be minimized (2X of 15 minutes or less of simmering each) as prolonged cooking is neither needed nor desirable. Works well in a microwave if allowed to stand following the each heating.

Hofmann et al. 1963 used a methanol extract, concentrated it to a low volume and cleaned it with petroleum ether. Heim & Hofmann . 958a had taken a residue from a methanol extract and cleaned it up with a successive series of solvents: petroleum ether, chloroform & chloroform-ethanol. The remaining residue was taken into the least possible amount of water and more contaminants precipitated with the addition of absolute alcohol. The residue remaining after the evaporation of the filtrate, was then passed through a column of cellulose using butanol saturated with water to elute and selection made for the appropriate fractions. For smaller quantities they used butanol saturated with water on ascending paper chromatography to separate.

Gartz l986a used dried powdered shrooms (2 gm) and extracted for 4 hours with petroleum ether (30 ml) and ether-chloroform ( 1 : 1) (30 ml) prior to soaking the recovered mushroom mass in methanol (100 ml) for 24 hours and isolated using preparative TLC with n-propanol-watcr-acetic acid (10:3:3) on 30 em ofkicsclgcl.
Neal eta/. 1968 found that using I() ml of methanol for each dried and powdered gram ofshroom shaken (mechanical) for one hour and this perfom1ed twice produced a clear solution but exhausted the marc of any detectable tryptamines.

Pederson-Bjergaard et al. 1997 used dried pulverized mushrooms (100 mg) in 3 ml of methanol in an ultrasonic bath for 15 minutes: repeated with 2 ml of methanol, to obtain a 98% extraction efficiency.
Christiansen et al. 1981 found methanol (hot) worked acceptably but only 91% of the psilocybin was extracted. They raised this to 98% by using 10% 1N ammonium nitrate in methanol. (They used 2X 30 minutes extraction times with a rotary mixer using a high potency mushroom.) (They also determined beat-drying shrooms removed 92% water by weight.)

Christiansen & Rasmussen 1982a used hot methanol to extract& Methanol- Water- 1M Ammonium salts (240:50: 1O) for preparative chromatography. (Buffered to pH 9.6 with 2 N Ammonia.)

" Psilocybin extraction": Taken from Anonymous 1992 as posted on the Internet. Printed in The Entheogen Review 3(2): 4.

Claimed to be derived from page 97 in Olah, Gyorgy 1970 Le Genre Paneolus: Essai taxonomique et physiologique.'(This work is currently unavai lab le to me so unable to verify.)

1. Dry the mushrooms (caps or mycelium).
2. Crush or grind to a powder.
(Note: For each of the following solvents use twice the dry
weight of the powder or enough to cover the powder well.)
3. Shake then allow to stand 30 minutes in Chlorofom1.
4. Filter and discard the Chloroform.
5. Shake then allow the residue to stand in Acetone
6. Filter and discard the Acetone.
7. Shake then allow the residue to stand in Methanol.
8. Filter.
9. Repeat 7 and 8 twice more.
10. Discard residue.
11. Combine Methanol extracts; evaporate to dryness.
The final product is a crude extract said to be a whitish-grey
crystalline substance. [Psilocin, if present, will be lost in step 4.]

Hofmann 1971 comments; " The synthetic production of psilocybin is much more rational than obtaining it from the mushrooms." [He was working with shrooms that contained 0.2-0.4% psilocybi]

Beug & Bigwood 1981 commented that extraction at higher temperatures or in a Soxhlet caused partial or complete loss of psilocin but generally less than a 20% loss of psilocybin. Methanol extracts stored at - 5° showed little changes after more than a year but within a few month storage at room temperature lead to

Interestingly, it appears that dried mushrooms with PSOH should be kept stored under freezing conditions, to prevent degradation, while those with ONLY PSOP or trivial amounts of PSOH can keep their potency (when dried) for many years even at room temperature.


Psilocin:

Free base:
White oil; then crystallizing
mp 103-104° (white crystals from ethyl acetate/ hexane)Shulgin & Shulgin 1997
mp 173-176° (prisms from ethyl acetate) Troxler et at. 1959
mp 173-176° (plates from methanol) Ott 1996
mp 173-176° (white crystals) Clarke's 1986
mp 173-176°(dec.) Perkal1981


Very sensitive to oxidation. Hofmann 1971
Forms plates from methanol; very slightly soluble
("difficultly"Pleased in water; unstable in solution, especially alkaline solutions. Merck 9th
Slightly soluble in water.
Soluble in methanol [See note by Kysi lka & Wu rs t 1990
below], ethanol, chloroform. Ott 1996
Soluble in ethanol and in dilute acetic acid (will be as acetate)
Clarke's 1986
Soluble in ether. Koike et al. 1981
Soluble in dilute acids
Soluble in dilute bases
Soluble in butyl chloride or chlorofonn [or others?]
Lee 1985

Crystal structures monoclinic Weber & Petcher 1974

Chloroform \ Water Partition coefficient: 5.52
Gessner et al. 1968 (this had been manually changed in the UT library copy to 3.30; Migliaccio et at. 1981 also gave this latter figure as that reported by Gessner)
Octaooi-Water partition coefficient: 0.68 (uncorrected);
1.45 (corrected for ionization)
Migliaccio eta/. 1981

pKa 8.47 (N); 11.33 (OH) Migliaccio et at. 1981
(Degrades above pH 7; Casale 1985)


Isolation:


Hofmann et al. 1958 & 1959
Cold & room temperature methanol have been employed by multiple workers successfully. Butanol or ethanol combined with acetic acid and water also appears to be an excellent solvent.

For direct consumption, simple extraction with lime juice and water works ex tremely well (color of solution is tawny not blue.)

Mushrooms were soaked for half an hour in methanol
( 15 ml for 2 gm of material) The methanol was removed and the residue dissolved in a 0.1 K sodium hydroxide solution (25 ml). This was then extracted with butyl chloride (25 ml) Evaporation of the butyl chloride apparenily left relatively pure Psilocin. (Alternately the butyl chloride was extracted with a dilute acid and the Psilocin migrated into the acid phase for spectroscopic purposes.)

There was no mention of the % of efficiency for either the initial extraction or any steps of the subsequent

Dried powdered mushrooms (210 gm) were combined with dilute acetic acid ( 100 ml) in a beaker. glacial acetic acid then used to bring the pH to 4. The beaker was allowed to stand for one hour and then heated for 8- I0 minutes in a boiling water bath. (Or until solution temperature reached 70°Pleased The beaker was then cooled to RT using running water and vacuum filtered through glass wool. After the filtrate was brought to pH8 using concentrated ammonium hydroxide, it was quickly extracted
twice with 50 m1 of ether. (Psilocin degrades at pH >7 hence the need for speed.)
To prevent emulsion formation they recommended a gentle mixing and not shaking.
After separation and combining, the ether is then dried over sodium sulfate, filtered and evaporated w ithout heat under nitrogen.
The greenish residue was crude Psilocin. White crystals were obtained by recrystallizing from Chloroform-Heptane ( 1 :3).
The product was said to be "reasonably pure." Casale 1985 (No indication of efficiency)

Kysilka & Wurst 1990 commented that due to the use of methanol as an extraction solvent by many workers, a lot of the published figures for PSOH content and prob-
ably notes of its absence were likely to be low or erroneous. They found that replacement of methanol with 75% aqueous ethanol and use of a longer extraction
time (160 minutes) provided them with an increase in yield. Ga1tz on the other hand apparently claimed completely opposite results

Hasler eta/. 1997 foun d addition of ascorbic acid to PSOH effectively prevented oxidation at RT but was inadequate for use during autoclaving.

Perkal 1981 found that purging with nitrogen dramatically helped prevent degradation of Psilocin. He also found it to be unstable in alkaline solutions but morestable than psilocybin under neutral or acidic conditions. Storage in the dark helped preserve his mushroom's activity even at room temperature.

 

Good quality Syrian rue (Peganum harmala) for an incredible price!
 
SWIMfriend
#2 Posted : 10/23/2012 5:05:24 PM

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Beautiful. A lot of info--and a lot contradictory.

We DO know beyond any doubt that hot water extraction is efficient and easy, since trip effects of mushroom tea are about the same level as direct ingestion of an equal quantity of dried material.

Soon I'm going to try some comparisons involving:

1) tea made steeped in boiling distilled water vs made with citrus juices added to water.
2) dried and reconstituted tea vs tea immediately used.

I'll post here when I have sufficient results (at least a month, for several tests, using personal "bio-assay" ).
 
SWIMfriend
#3 Posted : 10/24/2012 5:20:42 AM

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Here's quite a bit of practical extraction work from Psilocybe Fanaticus himself.
 
Jees
#4 Posted : 10/24/2012 6:23:14 AM

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Thank you for this thread Thumbs up
 
dondonaldson
#5 Posted : 10/27/2012 5:51:10 PM

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hey, nice thread for beginner like me..
thanks!Thumbs up
creative people
 
Morris Crowley
#6 Posted : 11/3/2012 8:37:03 PM

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For a historical perspective on psilocybin/psilocin and the mushrooms that contain them, Wasson gives us a good place to start. In 1962, he published a bibliography in the Harvard Univeristy Botanical Museum Leaflets covering a huge number of sources. Many of the entries, especially anthropological/historical ones, include a description of the source and the sort of information it contains.

I'm attaching the article to this post.


BibTex bibliography entry for the article:
Code:
@Article{WassonPsiloBiblio1962,
  Title = {The hallucinogenic mushrooms of Mexico and psilocybin: A bibliography},
  Author = {Wasson, R. Gordon},
  Year = {1962},
  Journal = {Botanical Museum Leaflets, Harvard University},
  Volume = {20},
  Number = {2},
  Pages = {25--73}
}
Follow me on Twitter (@morris_crowley) and on Facebook

Help us grow The Nexian
 
nen888
#7 Posted : 11/3/2012 11:05:45 PM
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..good idea for a thread endlessness..here's what i can add for now..

in https://www.dmt-nexus.me...spx?g=posts&t=27807 nen888 wrote:
Quote:
jamie wrote:
nen888 wrote: ( [...] i have addeded to text)
it worked vaporized!


it worked? Can you elaborate?
..in his final editorial of E.R. in 199[7]...Jim de Korne said that he had tried the 'Albert Hoffman' technique for psilocybin extraction (i posted this earlier in thread) and had produced a 'blue-grey crystal' which, vaporized, led to a 45 minute psilocin experience similar to a milder smoked DMT experience, but with it's own character (sounds a bit like DET)..it was probably not actually pure crystal, but sounds quite refined (compared to the dark brown gunk i got the one rushed attempt i had at this method [in the 90s, as a 'youth'] - this still had activity smoked, but was too mild for visuals [except light enhancement and very faint CEVs..good music/thought enhancement])
..he had written up this info in the journal before, and was surprised that no one else had reported trying it..i have been planning to try this properly one day..
.


the so-called 'Hoffman technique referred to above is in fact

Le Genre Panaeolus: Essai taxinomique et physiologique par Gyorgy Miklos OLA'H Laboratoire De Cryptogamie du Museum National D'histoire Naturelle 12, rue de Buffon, Paris. Memoire hors-series No 10, 1970. Page 97.
"Dry the mushrooms.
This important step is most likely to cause the greatest loss of yield depending on how it is done. Crush or grind the dried carpophores or mycelium to a powder.
Shake and allow to stand (e.g. 30 mins) in chloroform. Use maybe twice the dry weight in solvents at every step, or enough to well cover the powder.
Filter and discard the chloroform.
Shake the reidue and allow to stand with acetone.
Filter and discard the acetone.
Shake residue and allow to stand with methanol.
Filter.
Shake residue and allow to stand with methanol.
Filter.
Shake residue and allow to stand with methanol.
Filter.
Discard residue.
Combine methanol extracts.
Evaporate methanol to dryness, preferably in a vacuum, although low heat will do.

This will yield a crude extract containing the active tryptamines, suitable for most purposes. This can be further chromatographed on cellulose etc. to give pure psilocin and psilocybin. The recommended solvents are n-Butanol saturated with water, and n-butanol:acetic acid:water (24:10:10). Anyone wishing to do chromatography should check the relevant texts for more detailed instructions."


however, i think this method can be improved on without the need for Chromatography [see further on]
..from the same thread quoted above:
Quote:
..when i first read De Korne's statement 14 years ago it immediately struck me that there was no logical reason why freebase psilocybin/psilocin would not be active, and as potent as oral ingestion..it made sense that the duration was shortned..the onset was not as fast as DMT..

..so, the next time i see a big shroom fruiting season (which probably won't be for a while) i will adapt the 'Hoffman Proceedure' as follows:
1. Dry the mushrooms within 24-48 hours.
2. Crush the dried carpophores to a powder.
3. Add twice volume of chloroform (or other halogenated hydrocarbon non polar solvent).
Shake vigorously and allow to stand for 2-4 hours.
4. Filter and discard the chloroform.
5. Add chloroform as step 3, shake, stand for 30 minutes.
6. Filter and discard the chloroform.
7. Add twice volume of acetone, shake and stand for 1-2 hours.
8. Filter and discard the acetone. Probably repeat this step one more time.
9. Add 150% volume methanol, shake and allow to stand 4-8 hours. Filter, keep methanol.
10.Add methanol, repeat step 9, stand for less time. Filter, keep methanol.
11.Repeat methanol step third time. Discard residue.
12.Combine methanol extracts.
...at this point i am improvising..
13.Add NaOH+very small amount H20, or other basifying agent, until methanol somewhere between ph 9-12.
14.Evaporate methanol to dryness, preferably in a vacuum, or low heat will do.
15.Recrystalize solid from methanol. Store cold, away from air, light, moisture.

..vaporize 10-15mg [working up to] 30mg in glass chamber..

any suggested improvements? can't wait to try it again, in this fashion..[don't think i'll have the time this year..]

..would be great to hear from anyone who's actually chromatographed psilocin/psilocybin etc..

and from Extraction Method for the Isolation of Isolation and Identification of Psilocin from Hallucinogenic Mushrooms, J. F. Casale ;J. Forens. Sci. 30(1), 247-250 (1985)

Quote:
Several extraction techniques..have been used to isolate psilocin and psilocybin from more than two dozen species of mushrooms in four genera (Conocybe. Panaeolus, Psilocybe, Stropharia). The techniques that use methanol co-extract other compounds such as urea, ergosterol, ergosteral peroxide, α,α-trehalose, baeocystin, and norbaeocystin... At present, a useful aqueous extraction procedure has not been reported for psilocin and psilocybin.

Concentration and detectability of psilocin and psilocybin are dependent on several variables, including:
The absence of glucose, which will prevent the production of psilocybin.
Low levels of ammonium succinate, which will give poor yields of psilocybin.
The growing medium, which requires a pH of less than 7.
Timing: maximum production of psilocybin occurs on the seventh day after germination, while maximum production of the mycelium is reached by the ninth day.
Temperature: complete loss of psilocin and psilocybin will occur in harvested mushrooms left at room temperature for an extended period of time.
Oxidation: psilocin will oxidize to a blue product (possibly accounting for the bluing color in the four genera containing psilocin and psilocybin).

.

images below:
1. from [the mycellium-masters at] https://mycotopia.net/forums/bot...-crystal-psilocybin.html - psilocybin crystal needles;
2. from http://mycotopia.net/archives/d...us/messages/5/17249.html - less pure psilocybin xtals evapping;
3. from http://www.erowid.org/ar...silocin.extraction.html - mass spec of psilocin[cybin] after isolation method;
4. microscopic image of psilocin and psilocybin crystals.
nen888 attached the following image(s):
DSC01809.jpg (76kb) downloaded 1,097 time(s).
17678.jpg (22kb) downloaded 1,109 time(s).
psilo.xtract.fig1.gif (24kb) downloaded 1,102 time(s).
microscope images.gif (23kb) downloaded 1,098 time(s).
 
SWIMfriend
#8 Posted : 11/4/2012 12:28:23 AM

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What about the fact that the listed melting point for psilocybin is above 220 C (vs 40 C for DMT--and boiling point AT LEAST twice as high)?

Is it realistic that people have vaped at such high temperatures? Is it realistic that the molecule can survive such high temperatures in an oxygen environment?
 
nen888
#9 Posted : 11/4/2012 2:25:13 AM
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^..those melting points surely can't be for the freebase..? the quoted pH in the OP stats is 5.2..that's not FREEBASE..

?chemists...?
 
SWIMfriend
#10 Posted : 11/4/2012 2:57:37 AM

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I suppose that's right. If you can get it into a freebase form it would be reasonable to expect physical properties somewhat similar to DMT freebase.
 
SWIMfriend
#11 Posted : 11/4/2012 3:15:21 AM

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BTW, a bioassay test I carried out yesterday suggests to me that tea made in the usual way (from well-powdered mushrooms: steep, filter, steep, filter; making sure filters are ultimately squeezed for last drops) is actually only about HALF the strength of mushrooms taken in the usual way. I took a dose of powdered mushroom in plain, RT water, that was half the last dose I took as tea--and the effects were nearly identical (or even slightly stronger).

I'm quite sure about this. Keep in mind I am using the PE strain--I can only speak for that.
 
The Meddling Monk
#12 Posted : 11/6/2012 5:22:59 AM

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hi, newbie but oldie. but not a chemist, as such. just a meddler.
according to an old synthesis of Psilocybin http://www.erowid.org/ar...emistry/psilocybin.html
Quote:
The reported pH of a solution of psilocybin in 50% aqueous ethanol is 5.2. Anion exchange resin (OH- form) was added in portions, with vigorous and extended stirring, to the filtered reaction solution until the pH of the solution was 5.2. When this pH was reached, the resin was removed by filtration and the filtrate was concentrated under vacuum. The crude product was then recrystallized from a small amount of methanol, and a large volume of isopropanol, followed by storage in the freezer. Psilocybin (1) crystallized as long colorless needles.

isn't the phosphoroloxy aspect of Psilocybin (N,N-dimethyl-4-phosphoryloxytryptamine) what would make it naturally acidic? doesn't that make it like a salt of DMT? and then would basifying it effectively break off the phosphoros, hydrogen and oxygen? making it, well - dmt? or could pyrolisis do this? so i'm asking, isn't Psilocybin kind of like a form of DMT. also, i should have that old 1997 E.R. will post the Jim de Korne article when i can find it. i also recall him saying he had smoked psilocybin and it worked.


 
benzyme
#13 Posted : 11/6/2012 6:24:50 AM

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The Meddling Monk wrote:

isn't the phosphoroloxy aspect of Psilocybin (N,N-dimethyl-4-phosphoryloxytryptamine) what would make it naturally acidic?


no.

phosphoryloxy (and phosphate) groups have a partial negative character because of localized electrons due to the oxygens, which are quite electronegative. the amine group has a partial positive charge. alkaline hydrolysis of the phosphate would leave an oxyanion (O-) at the 4-position..this would not be dmt.
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The Meddling Monk
#14 Posted : 11/6/2012 9:02:18 AM

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thanks benzyme Smile. i hope i'm wiser soon.Surprised
 
benzyme
#15 Posted : 12/16/2012 11:43:06 PM

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SWIMfriend wrote:
If you can get it into a freebase form it would be reasonable to expect physical properties somewhat similar to DMT freebase.


no it wouldn't

for one, the OH has its own pKa. there are three possible species of psilocin at its isoelectric point, none of them above 50%. deprotonating the amine at a pH > 9.37 means giving the OH a negative charge.
since the OH a polar side group with a proton donor and acceptor, it readily absorbs moisture and undergoes autooxidation from air. proximity to the beta carbon likely also gives it unique physical characteristics.
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TheMystic
#16 Posted : 12/21/2012 5:47:11 AM

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Wow, I feel like such a fool. I am already scratching my head and saying what the F. I ony thought there was good old shroom tea, Texas Tea. Drink of choice when camping. Hey it is finally winter in Texas and cold enough outside to relax by the fire and gaze at the stars. I am afraid if I have a freebase that I can not get as many friends to share in the experience with me.

Anyhow I wanted to add my two cents.

"psilocybin is stable
enough to be detectable for many years in herbariums (Dried
psilocybin shrooms appear to remain usable for around 9 years
or sometimes longer if kept in proper storage; sbrooms wruch
contain psilocin o ften appear to rapidly degrade in storage)"


I have had very good resuelts from dried and then ground P-Subcubenis for 8 years when it was stored in a vaccume sealed container and left in the gun safe. As good as day one if not better.

Hoping next time. I will have a huge harvest and store them away just like before.
What this world needs is an enema.

The Mystic
 
Orion
#17 Posted : 4/19/2013 3:09:05 PM

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First here are two very seemingly similar techniques for the isolation of psilocin:

Quote:
An Aqueous-Organic Extraction Method for
the Isolation and Identification of Psilocin
from Hallucinogenic Mushrooms
J. F. Casale
J. Forens. Sci. 30(1), 247-250 (1985)
A representative sample of 2 to 10g of dried mushrooms is ground to a fine powder by mortar and pestle. The powder is mixed with 100 mL of dilute acetic acid in a 250-mL beaker. The pH is readjusted to pH 4 with glacial acetic acid. After standing 1 h, the beaker is placed in a boiling water bath for 8 to 10 min or until the internal temperature of the acid mixture reaches 70°C. The beaker is removed and cooled to room temperature under running water. The acid mixture is separated from the mushroom powder by suction filtration using glass wool. The filtrate is brought to pH 8 with concentrated ammonium hydroxide and quickly extracted with two 50-mL portions of diethyl ether. Gentle mixing instead of shaking should be used to prevent an emulsion. The ether is dried over sodium sulfate, filtered, and evaporated under nitrogen with no applied heat.
Crude psilocin will appear as a greenish residue. Recrystallization from chloroform/heptane (1:3) yields white crystals. The resulting powder can then be submitted to infrared and mass spectral analyses.


Quote:
The following method described shows an easy method to isolate pure psilocin from fungus in less than 4 hours. If a more pure product is wanted, the fairly pure psilocin can be recrystallized to produce large pure crystals.
20 grams of dried fungus is powdered in a coffee grinder to a fine powder. This is added to a glass container (~500 ml) along with 200 ml of distilled water and 40 ml distilled white vinegar (5% acidity). ~200 mg of vitamin C was also added to keep the psilocin from decomposing. This mixture was allowed to stir at room temperature for 1 hour and then the container was placed in a bath of boiling water to heat the mixture to 70 degrees C. After the mixture reached this temperature, it is filtered through multiple coffee filters (3-4 is good) and the filtered (be sure to squeeze out all the juice!) liquid is set into a cold water bath to cool it down. The extracted fungus is recovered and put into another container along with 150 ml water and 20 ml vinegar. This is again heated to 70 degrees C and then filtered as before. The filtrate is again cooled down and then added to the 1st extraction. The combined filtrates should give somewhere around 300 ml of liquid. Add about 30 ml of chloroform (xylene should also work, as psilocin is solubile in this as well) and begin stirring gently (you don't want emulsions, do you?). While stirring, SLOWLY add NaOH solution (~10 % NaOH is fine). I would suggest a drop by drop addition, as the pH can raise raphidly after a certain point. Target pH is 8, just try not to go over pH 9, as the alkaloids can decompose pretty fast at high pH. After the pH is at 8-9, continue to stir gently for about 20 minutes (electric stirrers are nice) and the psilocin will migrate into the chloroform (or xylene) layer. This is poured into a separatory funnel (or something similar) and the bottom chloroform layer is removed and set aside. The water layer is again stirred and 15 ml of chloroform is added for a second extraction. After 20 minutes of stirring, this is again separated in a separatory funnel and the chloroform recovered. These two chloroform extracts are combined and put into a small beaker. To this beaker, anhydrous MgSO4 is added (just oven dry epson salts in an oven at 450 degrees F for about an hour) to absorb any water. Usually only a gram or so is needed. Stir the chloroform with the MgSO4 for a minute or so and then filter through a "good quality" filter paper so you catch all the fine particles. The resulting chloroform layer will have a light yellow color. Now you have two choices:
You can evap the chloroform quickly to yield a fairly pure psilocin powder, or let it evaporate slowly to get larger and more pure crystals. Recrystallization can be carried out with methanol or a 3:1 heptane:chloroform. The recrystallized material is very pure and 20 mg is equivelent to 4-5 grams of mushrooms. Average yield for this method is about 60 mg of pure crystals (after recrystallization). The crystals do decompose at room temperature over time. The yellow crystals turn green in about a week or so if left out. To preserve the psilocin, put ~50 mg of psilocin in a small container and add ~50 mg ascorbic acid and 20 ml water. The psilocin will dissolve, but it does so slowly. You now have a solution with 2.5 mg psilocin per ml. This can be stored for many months in the refrigerator (possibly longer). An interesting note is that this "psilocin water" can be evaporated to give white needle crystals which don't seem to degrade at room temperature. Perhaps this is the way to stabilization!


Now I have some questions.

1: Firstly, why would it not be possible to simply precip from xylene with FASA?

2: I read somewhere that an ascorbate would still still degrade, and I think benzyme mentioned that a fumarate would not adaquately protect the psilocin? Is this correct?

3: I read that the psilocybin zwitterion behaves differently at a different pH, that it was also stable for days sitting at pH 12. Would it be possible to get it to migrate into something else at this pH in the same way as psilocin would into chloroform or preferably as mentioned above - can anyone confirm it works? - xylene.

4: Also what about changing psilocybin into some other salt form whilst still in solution then get it to migrate into an appropriate solvent? Would this be impossible because of the need to lower the pH too far with the appropriate acid ?
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Infundibulum
#18 Posted : 4/19/2013 4:11:58 PM

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1. we do not know whether psilocin is soluble in xylene. The second quote says xylene should work, but you know how internet is... for starters bufotenine freebase, an isomer of psilocin, can be pulled with chloroform or dcm, but NOT xylene, so the odds are against using xylene atm, but who knows? worth trying though and FASA-ing it.

2. It's all theoretical predictions - not hard data. I would personally do psilocin fumarate and a pinch of ascorbic acid, then add ethanol to a final 40-50% and store in the freezer.

3. No, even psilocybin "freebase" (a loose term here to describe net charge = zero, aka isoelectic point) which exists theoretically at a pH of 4, is still waaaay too polar to be pulled with xylene or other non-polar solvent.


4. makes no sense, chemically speaking - a possible way would be to convert the psilocybin to psilocin and then to the stable 4-Aco-dmt, then pull. But I doubt the later would happen in the conditions of a crude mushroom extract and of course would require some good chemical expertise. It's discussion would also be not allowed in this forum nexus either...


Need to calculate between salts and freebases? Click here!
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Orion
#19 Posted : 4/19/2013 4:52:36 PM

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Infundibulum wrote:
a possible way would be to convert the psilocybin to psilocin and then to the stable 4-Aco-dmt, then pull. But I doubt the later would happen in the conditions of a crude mushroom extract and of course would require some good chemical expertise. It's discussion would also be not allowed in this forum nexus either...


I suspected as much but why is this? Dmt to Dmt acetate is just the same in terms of the rules right ? Though I think the necessary chem for stabilizing psilocin as 4-aco is not quite so common for the kitchen chemist.

EDIT: And for anyone wondering how long the alcohol extractions last on their own, RR of shroomery (shroomery? pshhh! Wink ) said:

Quote:
Actually, pf's extraction tek with everclear rocks. My only change is to stop short of crystals for best storage life. Several years ago, I reduced a qp of dry fruits down to a shotglass worth of everclear, and it's been sitting ever since. Recently, I sampled it by squirting 1cc into a glass of orange juice. Trust me, after three years, it works.
RR


So it seems like the easiest way would be to just clean that stuff up as much as possible.
Art Van D'lay wrote:
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Those who know do not speak. Those who speak do not know
 
InMotion
#20 Posted : 4/19/2013 10:26:34 PM
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I would be very tempted to try the published extraction

An Aqueous-Organic Extraction Method for the Isolation and Identification of Psilocin from Hallucinogenic Mushrooms
J. F. Casale
J. Forens. Sci. 30(1), 247-250 (1985)

Sounds incredibly simple and reliable. They make no mention of inert atmosphere but that doesn't mean it isn't implied. I imagine ethyl acetate could be used instead of diethyl ether.

The other method orion also posted is the same thing just maybe more detailed.

If the FASA works, this could become a reasonable means for a laymen to acquire a reasonably pure psilocin extract. Think all that's needed is an experiment or three.
 
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