Psilocybin
Psilocin
H
N
H
N
HO
HO
N
O
P
CH3
CH3
N
OH
CH3
CH3
O
CAS Registry Number: 520-52-5
CAS Name: 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol
dihydrogen phosphate ester
Additional Names: O-phosphoryl-4-hydroxy-N,Ndimethyltryptamine
Trademarks: Indocybin (Sandoz)
Molecular Formula: C12H17N2O4P
Molecular Weight: 284.25.
Percent Composition: C 50.70%, H 6.03%, N 9.86%,
O 22.51%, P 10.90%
Literature References: The major of two
hallucinogenic components of Teonanácatl, the sacred
mushroom of Mexico, the other component being
psilocin, q.v. from the fruiting bodies of Psilocybe
mexicana Heim, Agaricaceae: Hofmann et al.,
Experientia 14, 107 (1958); Heim et al., Helv. Chim.
Acta 42, 1557 (1959); Heim et al., DE 1087321 (1960
to Sandoz). Structure: Hofmann et al., Experientia 14,
397 (1958). Synthesis: Hofmann, Troxler, US
3075992 (1963 to Sandoz). Crystal structure: H. P.
Weber, T. J. Petcher, J. Chem. Soc., Perkin Trans. II
1974, 942. Converted to psilocin in vivo. Toxicity data:
E. Usdin, D. H. Efron, Psychotropic Drugs and Related
Compounds (National Institute of Mental Health,
Rockville, Md., 2nd ed., 1972) p 138. Reviews:
Hofmann, Proc. 1st Int. Congr. Neuro-Pharm., Rome
1958, 446; Cerletti, Deut. Med. Wochenschr. 84, 2317
(1959); Hofmann, Bull. Narcotics 23, 3 (1971).
Properties: Crystals from boiling water, mp 220-228°;
from boiling methanol, mp 185-195°. uv max
(methanol): 220, 267, 290 nm (log 4.6, 3.8, 3.6). pH
5.2 in 50% aq ethanol. Sol in 20 parts boiling water,
120 parts boiling methanol; difficultly sol in ethanol.
Practically insol in chloroform, benzene. LD50 in mice,
rats, rabbits (mg/kg): 285, 280, 12.5 i.v. (Usdin, Efron).
Melting point: mp 220-228°; mp 185-195°
Absorption maximum: uv max (methanol): 220, 267,
290 nm (log 4.6, 3.8, 3.6)
Toxicity data: LD50 in mice, rats, rabbits (mg/kg):
285, 280, 12.5 i.v. (Usdin, Efron)
NOTE: This is a controlled substance (hallucinogen):
21 CFR, 1308.11.
Therap-Cat: Psychomimetic
CAS Registry Number: 520-53-6
CAS Name: 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol
Additional Names: 4-hydroxy-N,Ndimethyltryptamine; psilocyn
Molecular Formula: C12H16N2O
Molecular Weight: 204.27.
Percent Composition: C 70.56%, H 7.89%, N
13.71%, O 7.83%
Literature References: The minor hallucinogenic
component of Teonanácatl, the sacred mushroom of
Mexico. Isolated in trace amounts from the fruiting
bodies of Psilocybe mexicana Heim, Agaricaceae:
Hofmann et al., Experientia 14, 107 (1958); Heim et
al., Helv. Chim. Acta 42, 1557 (1959). Prepn: Heim et
al., DE 1087321 (1960 to Sandoz). Synthetic
precursor of psilocybin: Hofmann, Troxler, US
3075992 (1963 to Sandoz). Psilocin, the 4-hydroxy
analog of psilocybin, is formed by metabolic
dephosphorylation of psilocybin and is the active
species in the central nervous system: Horita, Weber,
Toxicol Appl. Pharmacol. 4, 730 (1962). Crystal
structure: T. J. Petcher, H. P. Weber, J. Chem. Soc.
Perkin Trans. II 1974, 946. Review: Hofmann, Bull.
Narcotics 23, 3 (1971).
Properties: Plates from methanol, mp 173-176°.
Amphoteric substance. Unstable in soln, esp. akaline
soln. Very slightly sol in water. uv max: 222, 260,
267, 283, 293 nm (log 4.6, 3.7, 3.8, 3.7, 3.6).
Melting point: mp 173-176°
Absorption maximum: uv max: 222, 260, 267, 283,
293 nm (log 4.6, 3.7, 3.8, 3.7, 3.6)
NOTE: This is a controlled substance (hallucinogen):
21 CFR, 1308.11.
#18. 4-HO-DMT / 4-HO-DMT PHOSPHATE ESTER
4-HO-DMT; TRYPTAMINE, 4-HYDROXY-N,N-DIMETHYL; 4-INDOLOL, 3-[2-(DIMETHYLAMINO)ETHYL]; N,N-DIMETHYL-4-HYDROXYTRYPTAMINE; 3-[2(DIMETHYLAMINO)ETHYL]-4-INDOLOL; CX-59; PSOH; PSILOCIN
4-HO-DMT PHOSPHATE ESTER; TRYPTAMINE, N,N-DIMETHYL-4-PHOSPHORYLOXY; 4-INDOLOL, 3-[2-(DIMETHYLAMINO)ETHYL], PHOSPHATE
ESTER; N,N-DIMETHYL-4-PHOSPHORYLOXYTRYPTAMINE; 3-[2-(DIMETHYLAMINO)ETHYL]-4-INDOLOL, PHOSPHATE ESTER; CY-39; PSOP;
PSILOCIN, PHOSPHATE ESTER; PSILOCYBIN
SYNTHESIS : To a solution of 0.50 g 4acetoxyindole (see preparation in the
recipe for 4-HO-DET) in 4 mL Et2O,
that was stirred and cooled with an
external ice bath, there was added,
dropwise, a solution of 0.5 mL oxalyl
chloride in 3 mL anhydrous Et2O.
Stirring was continued for 0.5 h and the
intermediate indoleglyoxylchloride separated as a yellow crystalline
solid but it was not isolated. There was then added, dropwise, a 40%
solution of dimethylamine in Et2O until the pH came to 8-9. The
reaction was then quenched by the addition of 100 mL CHCl3, and
the organic phase was washed with 30 mL of 5% NaHSO4 solution,
with 30 mL of saturated NaHCO3, and finally with 30 mL of saturated
brine. After drying with anhydrous MgSO4, the solvent was removed
under vacuum. The residue set up as crystals and, after
recrystallization from THF, provided 0.61 g 4-acetoxyindol-3-yl-N,Ndimethylglyoxylamide (80% yield) with a mp of 204-205 °C. Anal:
C,H,N.
A suspension of 0.38 g LAH in 10 mL anhydrous THF was
held in an inert atmosphere and vigorously stirred. To this there was
added, dropwise, a solution of 0.55 g of 4-acetoxyindol-3-yl-N,Ndimethylglyoxylamide in 10 mL anhydrous THF at a rate that
maintained a gentle reflux. After the addition was complete, the
refluxing was maintained for an additional 15 min, the reaction
mixture cooled to 40 °C, and the excess hydride destroyed by the
addition of water diluted with a little THF. The reaction mixture was
filtered free of insoluble material under a N2 atmosphere, the
resulting solids washed with THF. The filtrate and washings were
combined and stripped of solvent under vacuum. The residue was
distilled in a KugelRohr apparatus allized from EtOAc / hexane to
give 3-[2-(dimethylamino)ethyl]-4-indolol (4-HO-DMT, psilocin) as
white crystals which, after recrystallization from ethyl acetate /
hexane, had a mp of 103-104 °C. The final weight was 0.23 g (yield
56%). IR (in cm-1): 686, 725, 832, 991, 1040 and 1055; the OH
stretch is at 3240. MS (in m/z): C3H8N+ 58 (100%); parent ion 204
(15%); indolemethylene+ 146 (3%); 159 (2%).
Most of the early syntheses of psilocin and psilocybin
employ the O-benzyl ether as a protecting group. This provides more
stability to the chemical intermediates, but also requires the
additional step of reductive debenzylation. The flow chart of this
process is: conversion of 4-hydroxyindole to 4-benzyloxyindole via
the sodium salt, with benzyl chloride; the conversion of this with
oxalyl chloride to 4-benzyloxyindole-3-glyoxylchloride; the conversion
of this to 4-benzyloxy-3-(N,N-dimethyl-glyoxamide with anhydrous
dimethylamine; the conversion of this to 4-benzyloxy-N,Ndimethyltryptamine with LAH in dioxane; and finally the conversion of
this to 4-HO-DMT (psilocin) with hydrogen with a Pd catalyst on
Al2O3. The phosphate ester, psilocybin, requires two additional
steps: the conversion of 4-HO-DMT (as the sodium salt) to 4-(O,Odibenzylphosphoryloxy)-N,N-dimethyltryptamine, with dibenzyl
chlorophosphonate, followed by the catalytic removal of the benzyl
groups with hydrogen and Pd on Al2O3 to give the phosphate ester
of 4-HO-DMT (psilocybin). This product is much more stable in air
than psilocin, and is water soluble. The yields of this conversion are,
however, very bad, often less than 10%, and the two products
appear to be pharmacologically equivalent. Further, I have heard that
the phosphorylating agent dibenzyl chlorophosphonate must always
be used in solution as it is quite unstable as a pure reagent. The
fingerprint infra-red spectrum for psilocybin shows (in cm-1): 752,
789, 806, 858, 925 and the P=O stretch at 1110; the acidic OH
stretches are broad peaks at 2400, 2700 and 3200. The mass
spectrum is identical to that of psilocin.
DOSAGE : 10 - 20 mg, orally (as the indolol, the acetate or the
phosphate)
DURATION : 3 - 6 hrs
QUALITATIVE COMMENTS : (with 6.6 mg phosphate ester, orally)
"Something has started but I decide to join in a full dinner anyway.
The effects develop right through the meal, with some hints of animal
faces in the pork-chop bones. No movement, nothing flows, but it
probably wouldn't take much effort. Another hour and I am dropping
off already. The food? Somehow I doubt it. I would be completely
unable to tell this from, say, 80 milligrams of MDMA except that I had
a good appetite."
(with 7 mg, orally) "Basically I am not in a pleasant place -- quite
neurotic -- inwardly turned -- a touch of despair -- considerable visual
activity and if I were with someone I might find some sort of
reinforcement. The apathy and unpleasantness is ebbing now. My
mood might have been negative, and the psilocybin simply amplified
everything. There was some intensification of the lights and darks
around me."
(with 10 mg, orally) "Approximately forty minutes after the start, there
was a flutter and a very high, stimulated feeling, and gradually things
began to move very rapidly. It was astounding. When I closed my
eyes I saw so many fantastically beautiful patterns, textures, colors.
Everywhere I looked, eyes open, the colors were brilliant. The house
looked absolutely gorgeous and nature was simply spectacular. It
was a little frightening, almost too exciting, after the gentleness of
other substances. I could not believe that I was doing it, and that I
had the power within myself to see such beauty. I don't know how
long this went on but the motion was so rapid that I felt a sort of
motion sickness. Then I became quite nauseated and remained
nauseated the rest of the day, until things quieted down in the
evening, and then I felt absolutely wonderful."
(with 15 mg, orally) "My 'early warning system' alerted me at fifteen
minutes, then all was quiet for a while. I start building up again, and I
am awfully glad that I am familiar with this transition. Visual
distortions. Things distract me. I can't find the cap to my pen -- must I
keep writing forever? At this point I couldn't drive, let alone write, and
it is just a bit more than a half hour since I took it. The furniture in my
office is moving up and down. I lie down, and close my eyes. THIS is
where it is at. Visuals are wild. Even with eyes open, with no visual
target, there are imaginative visual effects. I imagine a dark room
with a fire place going in the middle of the night, with no other inputs,
and with my eyes closed I have the body image of being seated in
front of that fire and I am amazed by the hallucinations and
distortions I am seeing there only there is no fireplace as I am still
lying in my darkened bedroom. Sort of a 2x removed hallucination.
This is a night-time drug -- the day-light washes everything out. I
tried but could not repeat the fireplace thing, and must be dropping
rapidly. At three hours I ask if I would try some other experiment. OK,
but there are some reservations. At four hours, no reservations."
(with 15 mg, orally) "As soon as I felt the chill and the alert, I lay
down and closed my eyes. Indian motif. Abundant fruits, vegetables,
leaves, straw, wood, vines. Very responsive sexually. Beautiful,
stern, rich encounter with livingness and Indian Gods and serenity.
Color and peacefulness. A couple of hours, then elaborateness
dropped slightly. At this point top of temple easy, but it was a South
American temple, with earth floor, straw, vines full of fruit. Familiar
feeling. We are naked and we are children-adults, daring to be there,
regarded benignly (stern, amused) (rising through the floor). This is
one of the true ones, this plant experience.
1970, our Federal drug law, there are only four plants listed as being
"Scheduled Drugs." In Schedule I there was Marijuana (later defined
as the plant Cannabis spp.) and Peyote (later defined as the
botanical Lophophora williamsii); in Schedule II there was Opium
poppy and poppy straw, and Coca leaves. It is generally known that
commercial opium comes from the plant Papaver somniferum and
that commercial coca comes from the plant Erythroxylon coca, but I
(with 12 mg phosphate ester, intramuscularly) "This is strong. There
am not aware of either of these botanical binomials having been
were a lot of wild images in about two hours, and I thought that the
explicitly named in the statutes. A couple of quickies were slipped in,
day would never end. At about six hours I knew it would, but in fact in
not completely properly, in the giving of the binomial of Tabernanthe
the evening I took 100 milligrams of seconal which allowed me to
iboga as a synonym for ibogaine, and the giving of the binomial of
drift into a fine sleep. The next day I was fine."
Catha edulis as a synonym for cathinone, both Schedule I drugs. So
there are definitely four, and maybe six, plants that can be
considered Scheduled drugs.
(with 3 mg phosphate ester, intravenously) "The effects are
But nowhere in the legal archives of current drug statutes
immediate (in 30 seconds) and I did not have the time to build up any
can you find mention of Genera such as Psilocybe, Stropharia,
worry -- it was simply too fast. In about an hour I was back where I
Paneolus or Inocybe. Nor of the dozens and dozens of species that
started from."
stem from them. So, you would logically conclude that these magic
mushroom are not illegal? Well, yes and no.
(with 12 mg phosphate ester, intravenously) "I had had eight
No, in the letter-of-the-law sense that they are not explicitly
milligrams earlier, with a very good reaction. Here, today, I feel that
named as illegal entities. But yes, in the de facto exercise of the law.
everything has disintegrated, and I am extremely anxious. I am very
With the inescapable fact that both psilocin and psilocybin are
confused."
named as Schedule I drugs, and the acknowledgment that there are
some mushrooms that might contain these drugs, then these
botanical entities become legal complications. Might the dried fruiting
Psilocybe cubensis: (with 1.5 g, orally) "At best, some speckled
bodies be seen as packaging strategy for the sale and delivery of a
patterning with my eyes closed, and in general a light intoxication.
Certainly not the sparkle of LSD. Dropped quickly and felt heavy and Scheduled I drug? Might the growing of them be seen as a
production strategy for the manufacture of a Schedule I drug? Of
tired, good sleep."
course it might be, as the law has stated that the manufacture and
sale of Schedule I drugs is a Federal felony. "Your Honor. I gathered
(with 3.5 g, orally) "Took a gram to start with, and it started in ten
these things out there in the field for my dinner salad. I had no idea
minutes, but not strong enough, so did the other 2.5 grams.
that they contained something illegal." A reasonable defense, and it
Everything was coming at me in waves, boxing me in, the visuals
may well work today, along with the argument that opium poppy pods
were in waves and in dark earth colors, orange and brown, not the
are buyable at the Farmer's Market as floral decorations, and
wide spectrum of acid. I was sea-sick, and vomiting helps some, and morning glory seeds can be bought at the local nursery for next
a little dope quieted the tummy. Started dropping, and everything
Spring's garden. Innocence may be a virtue for a while, as it is not
became very good, and by midnight I was out. No hangover at all."
widely recognized that these decorative poppies are in fact Schedule
II opium capsules and those Ipomoea seeds in fact contain ergine, a
EXTENSIONS AND COMMENTARY : There are two generalizations Schedule III depressant. But that is today. What happens tomorrow?
Today, to a large measure, the burden of proof still falls
implicit here, one of which I am quite at peace with, but the other is
upon the accuser, and that ephemeral and undocumented
both complex and disturbing. The OK item is the casual equation
"presumption of innocence" concept provides some measure of
between the hydroxy compound psilocin, the acetate ester, and the
phosphate ester, psilocybin. As I had discussed in the CZ-74 to CEY- protection. They, the accusors, must prove you are guilty. But, as the
legal structure drifts from the criminal statutes to the regulatory
19 entries in 4-HO-DET, there is no proof that the ester goes to the
indolol metabolically, but it is a good guess, and there have been no statutes, this protection is lost. You must prove that you are innocent.
The perfect example is the random urine test, which demands,
demonstrated differences in their pharmacology. Ditto here, with
without any probable cause, that you prove that you do not have
psilocin and psilocybin. I have explored both of them as pure
drugs in you. There is no presumption of innocence. This has been
chemicals, and I find them completely interchangeable as to their
the sad state of our income tax laws for years, and now it is
pharmacological properties.
becoming a reality in our drug laws. Prove to the court that you didn't
The second generalization is more difficult and leads into
know that these mushrooms were psychoactive! Shades of the
some uncomfortable areas. This is the effort to equate the
Inquisitions of a few hundred years ago. Or the Salem travesties of
chemicals, psilocin and psilocybin, with their natural sources, the
more recent times. Prove to us you are not a witch.
mushrooms. Part of the uncertainties I feel are related to the
There is quite a body of scientific literature that discusses
unknowns that are intrinsic to the plant sources. There are many
species that have been offered and accepted as magic mushrooms. the changes (increases and well as decreases) of psilocybin and
psilocin content in mushrooms as a function of their nutrient diet.
Identification in the field is one thing, but what can be said of dried,
And, under the 4-HO-DET entry, I mentioned that the inclusion of an
ground up plant material of unknown sources? What are they? How
unnatural component into the diet just might produce an unnatural
have they been preserved? What is their composition? The older
alkaloidal product, with an exploitation of the natural and available
samples may be reasonably free of the rather unstable psilocin, but
enzyme systems that are part of the mycelial structure.
psilocybin is much more stable and may persist. But so might its
Another aside. There is a trivial, and fun, bit of
congeners such as baeocystin and norbaeocystin which are
nomenclature which I have used for years. I have, in my notes,
scattered in widely different proportions in many species, and which
referred to psilocybin as PSOP (because of the phosphate thing) and
are quite unexplored pharmacologically. There are so many
psilocin as PSOH (because of the exposed OH group). I have gotten
uncontrollable variables in the mushroom area that here I cast my
into the habit of referring to the acetate as PSOA, the O-methyl ether
vote for exploration with the chemicals themselves. They can, at
as PSOM and the chemical intermediate O-benzyl ether as PSOB. I
least in principle, be analyzed, and weighed. But this is a luxury not
available to many, as the syntheses of these alkaloids is difficult, and know that this will never catch on, but I still do it because it is
convenient and a bit campy. One code that is not mine, but
woefully illegal.
Sandoz's, is CMY for 1-methyl-psilocin. I know it has been looked at
Which brings us back to the mushrooms, and the topic of
in a clinical environment, but I have not idea as to its activity. It is a
the law. In the original writing of the Controlled Substances Act of
simple thing to make. I would love to know what it does
Extraction and analysis of indole derivatives from fungal biomass
by Jochen Gartz , Journal of Basic Microbiology, Vol 34, 1994; 17-22
Abstract: The occurence and extraction of indole
derivatives in six species from four genera of higher fungi
were investigated. By using pure methanol for extraction of
the mushrooms analysis revealed the highest concentrations
of psilocybin and baeocystin. The psilocin content of the
species was higher by using aqueous solutions of alcohols
than with methanol alone but was an artificial phenomenon
caused by enzymatic destruction of psilocybin. The
extraction with dilute acetic acid yielded better results than
with the water containing alcohols. The simlpe one-step
procedure with methanol for the quantitative extraction is
still the safest method to obtain the genuine alkaloids from
funghal biomass.
Sebek were studied by using methanol and the
recommended mixtures of sol vents (Casale 1985, Kysilka
and Wurst 1990, Wurst et al. 1992), respectively.
Materials & Methods
Fungal material: Cultivated mushrooms: Psilocybe
semilanceata (FR.) Kumm from horse manure compost
(Gartz 1991); Psilocybe cubensis (Earle) Singer grown on
cow dung/rice grain mixture (Gartz 1989a); P. bohemica
from rice grain/water (Gartz and Mueller 1989; Gymnopilus
purpuratus (Cooke and Mass) Singer from rice grain/saw
dust medium (Gartz and Mueller 1990, Gartz 1991).
Naturally grown mushrooms: Panaeolus cyanescens
(BK & BK) SACC. (leg. Oahu, Hawaii 13.11.88); Inocybe
Comments:
aeruginascens Babos (leg. Potsdam 20.05.1987); P.
The abstract says it, if you are planning to extract the
bohemica Sebek (leg. near Sazava, Czech Republic
alkaloids from either dries and pulverisized fruiting bodies
15.11.89).
or from mycelium it is best to use pure methanol. Superior to
All basidiocarps were dried at room temperature.
aqueous solutions of alcohols (which is wet alcohol, the one Possible present residual water was removed from the
you are likely to have!) is dilute acetic acid which means
mushrooms by freeze-drying. Voucher speciments of each
simple vinegar (better: vinegar essence diluted with same
species have been deposited in the herbarium of the
amount of water) which is quite nice because there is no
Univeristy of Leipzig (LZ).
problem obtaining it. The problem with wet alcohol is that
Extraction: (Samples (0.01 - 0.1 g) of dried ground
the enzymes which dephosphorylise Psilocybin to the
mushrooms were extracted with 5 to 20 ml of methanol for
instable Psilocin are also extracted from the biomass. This
0.5 to 12 hours by using a magnetic stirrer at room
also occures with acetic acid but to a smaller amount and
temperature. Under equal conditions the mixtures with
does not occure at all with pure methanol (ethanol?). The
aqueous acetic acid (Casale 1985) and a queous ethanol
recommended extraction time (magnetical stirring) is with
(psilocin) and methanol (psilocybin) (Kysilka and Wurst
methanol 12h at room temperature or 1h at 45 deg.Celsius, 1990, Wurst et al. 1992) were used for extraction of the same
no times given for the acetic acid method. And the moral:
batch of mushrooms. In the cases with aqueous alcohols as
Dont use clandestine-quality alcohols for extraction, use
solvent a different extraction time for psilocybin (10 min)
vinegar ! Or dry the alcohol by adding salts like MgSO4,
and psilocin (160 min) was performed (Kysilka and Wurst
CaCl2, NaSO4 which were previously dried in an oven and 1990). By using of dilute acetic acid the solution was placed
decand or filter the solvent from them after a day or longer. in a boiling water bath for 10 min after extraction and
anaysis and was then analysed 10 min after extraction and
In the last 15 years many papers have been
analysis and was then anal ysed again (Casale 1985).
published about the occurance and determination of
The filtration and analysis of the indole derivatives
psychotropic tryptamine derivatives like psilocybin, psilocin by using HPLC and TLC were described elsewhere (Gartz
and baeocystin in fungi (Gartz 1992, 1993).
1987, Semerdzieva et al. 1986, Wurst et al. 1992). An
Various extraction procedures of these substances
analysis of the extracts for enzymes of the phosphatase type
from mushrooms have been ised mainly with methanol as
was also carried out (Weber a nd Horita 1963).
solvent (Beug and Bigwood 1982, Gartz 1987, Sottolano and
Lurie 1983).
Results
In 1985 an aqueous-organic extraction method with
In this investigation the extraction of psilocin,
acetic acid for these compounds was described (Casale
psilocybin and baeocystin with pure methanol was not
1985). Recently, Czech analysts have used aqueous solutions completely after 30 min in all species and even 6 hours in
of methanol and ethanol (pure or in presence of potassiumanalysis of P. cubensis and G. purpuratus. But the full
nitrate) for extraction of the indole derivatives in Psilocybe
extraction of the alkaloids from al l mushrooms was reached
bohemica Sebek (Kysilka and Wurst 1990, Wurst et al
after 12 hours. After this time no traces of indole derivatives
1992). They claimed that it was possible to have found more could be detected after subsequent extraction of the fungal
psilocin with aqueous ethanol extraction than with pure
material with aqueous solutions of ethanol/methanol or
methanol and that a dissimilar extraction of the alka loids by acetic acid as well as with chloroform for psilocin.
using both new systems could be achieved. In this work the
Baeocystin as incompletely methylated counterpart
extraction procedures of psilocybin, psilocin and baeocystin and possible precursor of psilocybin (Gartz 1989a) was
from varoius mushroom species including P. bohemica
found in all species by using methanol but in some cases
only in very small amounts (Table 1).
The psilocybin and psilocin content was in the
same order of magnitude as that found earlier (Gartz 1992,
1993). This substance seems to be a phosphoric acid ester
like psilocybin and baeocystin. Similar concentrations of
psilocin were detected in the extracts of P. cubensis and G.
purpuratus by using an aqueous solution of acetic acid
versus pure methanol (Table 2).
By using the new solvent mixtures containing
ethanol and methanol for extraction it was found that more
psilocin could be detected in extracts of every species but
always smaller amounts of psilocybin than with pure
methanol (Table 3).
Additionally, a high activity of enzymes of the
phosphatase type could be detected in these aqueous
solutions from all species. In contrast to these results only
the extracts of P. cubensis and P. cyanescens showed a
significant enzymatic activity b y using acetic acid as
solvent. In these cases psilocybin was completely
dephosphorylated to psilocin by heating the acid extracts and
no baeocystin could be detected in P. cyanescens.
Discussion
It is well known that an extraction procedure with
methanol needs much time (up to 12 hours) at room
temperature (Beug and Bigwood 1982, Gartz 1987,
Semerdzieva et al. 1986) or one hour at 45 C
(SCOTTOLANO and Lurie 1983) for complete extrraction.
In our investigations psilocin could be found in
high concentrations as well as psilocybin after simple
extraction with methanol from various species (Gartz 1987,
1989c, 1991). When undertaking quantitave analysis of
levels of indole derivatives after biotransformation of
tryptamine and similar compounds in fruiting mycelia of P.
cubensis the highest concentrations of psilocin in every
mushroom for example could be detected by using methanol
(Gartz 1989a, b). By using aqueous methanol and ethanol as
so lvent for analysis of P. bohemica the Czech analysts have
not always analyzed the same batch of mushrooms during
their comparative study of extraction methods (Kysilka,
pers. communication 1989).
We generally found variations from one mushroom
to another in every species even within P. bohemica from a
single location (Gartz and Mueller 1989) and also in
controlled cultures (Gartz 1991). Additionally, the high
activity of enzymes of the phosphat ase type in the aqueous
solutions of alcohols was already described in aqueous
mycelial extracts of P. cubensis and other psilocybin
containing mushrooms many years ago (BOCKS 1968,
Gartz 1993, Weber and Horita 1963). These enzymes were
also extracted wit h the water containing solvents and caused
a partial dephosphorylation of psilocybin to psilocin (Tables
1 and 3). By using these aqueous soluions it was also
observed that in some cases bluish mixtures have been
resulted after extraction as a sign of par tial oxydation of
psilocin (BOCKS 1968, Gartz 1989a, Weber and Horita
1963). It is also interesting that most of the baeocystin was
destroyed during the extraction procedure with water
containing alcohols (Tables 1 and 3).
Casale (1985) described the rapid formaion of
psilocin after complete dephosphorylation of psilocybin by
heating the dilute acetic acid extract. It is now quite clear
that the decomposition under these conditions is an
enzymatic reaction and was not ca used by the acid alone.
For example the phosphoric acid ester psilocybin, baeocystin
and aeruginascin in these acidic extracts from I.
aeruginacens were stable during heating in contrast to the
behaviour of the same alkaloids in solutions of P. cubensis a
nd P. cyanescens. It seems that active enzymes of the
phosphatase type could be extracted with aqueous acetic
acid only in these two species in contrast to water containing
alcohols as extraction method. In the past attempts at the
sparation of psilocybin and psilocin simply using mixtures
of organic solvents and water were also unsatisfactory
(THOMSON 1980).
This investigation shows that the high percentage of
psilocin detected in P. bohemica (Kysilka and Wurst 1990,
Wurst et al. 1992) and not found earlier (Gartz and Mueller
1989) was an artificial phenomenon casued by enzymatic
destrucion of psilocybin w hich is common in different
species by using water containing organic solvents.
Extraction with pure methanol is the safest method to obtain
the genuine indole derivatives from mushroom species of
various genera.
Acknowledgements
The author thanks the following persons: G.
Drewitz, J. Allen, G.K. Mueller and M. Semerdzieva who
geneously supplied herbarium material and/or valuable
information.
References #
Beug MW, Bigwood J. 1982. Psilocybin and psilocin levels in twenty species from several
genera of wild mushrooms in the Pacific Northwest, U.S.A. J. Ethnopharm, 5, 271-289.
Bocks SM. 1968. The metabolism and psilocin and psilocybin by fungal enzymes. Biochem. J.,
106, 12-13.
Casale JF. 1985. An aqueous-organic extraction method for the isolation and identification of
psilocin from hallucinogenic mushrooms. J. Forensic Sci., 30, 247-250.
Gartz J. 1985. Zur Isolierung des Baeocystins aus den Fruchtkoerpern einer Psilocybe-Art.
Pharmazie, 40, 274.
Gartz J. 1987. Variation deer Indolalkaloide von Psilocybe cubensis durch unterschiedliche
Kultivierungsbedingungen. Beitraege z. Kenntnis d. Pilze Mitteleuropas, 3, 275-281.
Gartz J. 1989a. Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe. J.
Basic Microbiol., 29, 347-352.
Gartz J. 1989b. Biotransformation of tryptamine in fruiting mycelia of psilocybe cubensis.
Planta Med., 55, 249-250.
Gartz J. 1989c. Occurence of psilocybin, psilocin and baeocystin in Gymnopilus purpuratus.
Persoonia, 14, 19-22.
Gartz J, Mueller GK. 1990. Analysis and cultivation of fruit bodies and mycelia of Psilocybe
bohemica. Biochem. Physiol. Pflanzen, 184, 337-341.
Gartz J, Mueller GK. 1990. Versuche zur Kultur von Gymnopilus purpuratus,
Purpurflaemmling. Myk. Mitt. blatt (Halle), 33, 29-30.
Gartz J. 1991. Further investigations on psychoactive mushrooms of the genera Psilocybe,
Gymnopilus and Conocybe. Ann. Mus. civ. Rovereto (Italy), Sez. sc. nat.,7, 265-274.
Gartz J. 1992. New aspects of the occurance chemistry and cultivaion of European
hallucinogenic mushrroms. Ann. Mus. civ. Rovereto (Italy), Sez. sc. nat., 8, 107-124.
Gartz J. 1993. Narrenschwaemme. Psychotrope Pilze in Europa in Europa. Herausforderung an
Forschung und Wertsystem. Editions Heuwinkel. Genf/Neuallschwill.
Kysilka R, Wurst M. 1990. A novel extraction procedure for psilocybin and psilocin
determination in mushroom samples. Planta Med., 56, 327-328.
Semerdzieva M, Wurst M, Koza T, Gartz J. 1986. Psilocybin in Fruchtkoerpern von Inocybe
aeruginascens. Planta Med., 47, 83-85.
Sottolano SM, Lurie IS. 1983. The quantitation of psilocybin in hallucinogenic mushrooms
using high performance liquid chromatography. J. Forensic Sci., 28, 931-935.
Thomson BM. 1980. Analysis of psilocybin and psilocin in mushroom extracts by reversedphase high performance liquid chromatography. J. Forensic Sci., 25, 779-785.
Weber LJ, Horita A. 1963. Oxydation of 4 and 5-hydroxy-indole derivatives by mammalian
cytochrome oxydase. Life Sciences 1, 44-49.
Wurst M, Kysilka R, Koza T. 1992. Analysis and islolation of indole alkaloids of fungi by highperformance liquid chromatography. J. Chromatogr., 593, 201-208.
Table 1.
Amount of indole alkaloids in fruiting bodies of different species by using pure methanol as solvent (%, dry weight).
Species
Psilocybin
Psilocin
Baeocystin
P. semilanceata
0.98
-
0.34
P. bohemica
0.85
0.02
0.04
P. bohemica (cultivated)
0.93
0.04
0.02
P. cubensis
0.63
0.11
0.02
G. purpuratus
0.34
0.29
0.05
I. aeruginacens
0.40
-
0.21
P. cyanescens
0.32
0.51
0.02
Table 2.
Concentraction of alkaloids by using acetic acid for extraction of the dried mushrooms (%, dry weight).
Species
Psilocybin
Psilocin
Baeocystin
P. semilanceata
0.97
0.15
0.11
P. bohemica
0.60
0.21
-
P. bohemica (cultivated)
0.65
0.28
-
P. cubensis
0.45
0.25
-
G. purpuratus
0.24
0.35
0.01
I. aeruginacens
0.32
0.05
0.15
P. cyanescens
0.20
0.61
-
Table 3.
Results of the mushroom extraction of six species using aqueous mixtures of methanol and ethanol (%, dry weight).
Species
Psilocybin
Psilocin
Baeocystin
P. semilanceata
0.80
0.15
0.11
P. bohemica
0.60
0.21
-
P. bohemica (cultivated)
0.65
0.28
-
P. cubensis
0.45
0.25
-
G. purpuratus
0.24
0.35
0.01
I. aeruginacens
0.32
0.05
0.15
P. cyanescens
0.20
0.61
-
PF TEK SHROOM EXTRACTION
This technique describes how to extract psilocybin
from magic mushrooms with pure 190 proof ethyl alcohol
and make a magic mushroom liqueur of concentrated
psilocybin to effect a powerful psychedelic dose as potent as
desired. The entire process involves only the shrooms and
alcohol. The alcohol is untainted with chemicals and poisons
because it can be easily acquired from a liquor store (United
States) either over the counter (in some states) or with a
special permit (most states - see end of article section "procuring 190 proof ethyl alcohol from a liquor store").
mouth of a drinking glass. Squeeze the filter and slurry to
extract the alcohol. There are many details to deal with, but
doing it once reveals them all. Experience is the best teacher.
Store the extracted alcohol in a fresh bottle.
EVAPORATION AND CONCENTRATION
Combine the alcohol extracts into a glass. Place a
small electric fan (small desk clip on fans are perfect) near
the glass and point the air flow directly down into the glass
until the surface of the alcohol ripples. This will speed the
evaporation and concentration. The process will take several
ALCOHOL EXTRACTION
hours. The more alcohol extract - the longer the evaporation
time. As the alcohol evaporates and the level recedes down
1. Acquire quality psilocybe cubensis shrooms
into the glass, wash the residue that adheres to the inside of
(harvested before or just as the veils open and cool dried
the glass back into the solution. Any fumes that are
with desiccant). The more shrooms used in the beginning,
the more potent the concentration can be when finished. Use generated will be harmless because the alcohol is a non
poisonous drinkable spirit. Keep flames away from the
at least several grams of dried shroom material to make the
solution - pure alcohol is very flammable.
process worthwhile and effective. The shrooms need to be
One can also use heat to evaporate and concentrate
thoroughly dry (rock hard) to allow pulverization. To
the
elixir.
Use a double boiler type of set up to heat and
pulverize the shrooms, put them into a small strong zip lock
plastic bag (freezer bag), cover the bag with a magazine (for evaporate off the alcohol to concentrate the elixir.
The concentrated shroom liqueur will have a
protection of the bag) and pound it with the rubber heel of a
pungent mushroomy aroma (like fungi perfume). Also, a
large shoe. Or, powder them in a small canister type coffee
white crystalline kind of precipitate will form in the alcohol
bean grinder.
elixir (see above photo). Store it in small screw cap bottles
In a heat resistant soaking vessel (pyrex glass),
or vials in the freezer. Alcohol doesn't freeze solid and will
combine the shroom powder with several times its volume
remain liquid.
with 190 proof Everclear (ethanol). This is the "slurry".
Place the soaking vessel in a pan of boiling water. Raising
SUPPLY LIST
the soaking vessel off the bottom of the hot water pan is a
good idea for preventing serious sticking of the good
extracts. The slurry will start to boil. Turn the water boiling
shrooms
pan heat down and let the slurry sit for a few hours at a
190 proof ethyl alcohol (GOLDEN GRAIN warm-hot temp. Alcohol boils at a lower temp than water.
EVERCLEAR ect)
Watch the temperatures closely. Things can get totally out of
Pyrex glass wide mouth slurry soaking vessel
hand and ruined very quickly without close attention paid.
funnel and filtering set up - or
While the slurry is still hot, filter it through filter
dust-pollen masks
paper. This is probably the most important part. A good
small desk fan
filtration will be efficient and will keep most of the shroom
material out, making for a clean extraction (clean of shrooms
Here are some important guidlines for right now!
that is - but heavy on psilocybin). A small lab type vacuum
pump powered bottle top filtering funnel with filter disk
There is one thing about magic shrooms that is
holder makes it all really easy and fast, with little waste.
universal. Anyone that you know that has taken magic
That is why this extraction idea is really only for the
shrooms will tell you one thing, if asked, and that is that the
fanatics.
shrooms were were hard on the stomach. They make most
Collect and save the filtrate liquids. Heat the slurry people sick, at the least, temporarily, and some get very sick.
(the mush in the filter paper) one or two more times with the What makes for the sickness, is that these magic shrooms are
190 proof as before, filter, and accumulate the liquids of the not easy to digest. It is the stomachs reaction to difficult to
extractions. The photos at the top are of extractions done
digest food that is the sickness. So they goal would be to
twice.
elliminate the stomach, or by pass it. These extraction teks
Inexpensive dust-pollen masks make excellent
can do that. By making the extract very potent and using
filters for the slurry. These are available at hardware, drug
good filtration technique, the product can be consumed by
and paint stores. They are usually white or tan colored, fit
mouth so that the saliva and the mucous membranes in the
over the nose and mouth and are held on to the face by a
mouth do most of the job. So when anything of the extract
rubber band attached to the filter. Fashion the filter over the reached the stomach, it is basically digested leaving the
stomach with nothing to do which results in no stomach
upset - just the trip. This is the greatest idea in magic shroom
history. To elliminate the ugly physical effects is a real
godsend. It makes it all totally superb and beyond any
known psychedelic in entheogenic quality and potency.
1. Use warm-hot temps when soaking the initial slurry
(shroom-alki). Use the hot water bath idea from the
Gottlieb tek below. Avoid hot bottomed slurry soak
vessels. The good stuff can bake on and stick very easily.
2. A good filter is a must. Lab quality filter paper helps for a
cleaner extract (less shroom stuff). The fanatic should get
a little bottle top vacuum filtering funnel with a hand
squeeze vacuum pump and fine slow flow filtering papers.
(science supply - not cheap - but affordable for the
fanatics - look for the 47 millimeter filter sized set ups small but perfect for this).
3. When filtering the slurry, do it while it is hot.
4. The crystals when heated in the initial slurry are free base
molecules. In the final liqueur on cool down, the free base
molecules will coalesce and form crystals. It takes a day
or two for the process to be complete. The smaller the
final amount of liqueur, the easier it is for the molecules to
meet each other and combine. When you get your final
magic liqueur, the free base psilocybin will coaslesce and
form whitish crystals. At first they might look like whitish
glue, but they transform in solution to hard crystals.
5. The final elixir will have a layer of crystals on the bottom
of the storage vessel. The freebase Psilocybin molecules
come together fast in the cool alcohol. When it is time for
dosage, reheat the crystal liqueur in its storage vessel in a
pot of hot water. Boil the liqueur and stir and scrape
deposits from the glass as the liqueur boils lightly. Alcohol
boils at a lower temperature than water. Keep the storage
vessel off the bottom of the boiling water pot. Direct heat
is very bad for the elixir, making it stick. As the liqueur
boils, the crystals will remelt with time. The large particles
of the crystals can be crushed with a long needle probe to
hurry up the process. When the crystals are gone,
administer the magic liqueur while it is HOT. Using a
syringe enables uniformity and accuracy of the doseages.
The hot liqueur quickly becomes cloudy on slight cooling.
So a hot temp of the liqueur with remelted crystals is
important for accurate dosage administration. Or the
crystals can be dried and used as they are!
6. Or, the crystalline extract can be completely dried by
placing the elixir container in front of a small fan to get
most of the liquid out. To complete the drying, desiccant is
recommended. Place the small vessel of liquid extract into
a larger jar with quality desiccant. It takes several days to
complete drying, but the final crystalline substance is very
dry, loose, and can be weighed and worked with very
easily.
7. TEK personalization through experience is what happens
to anyone trying this.
DOSAGE and STORAGE
Getting crystals is really moot. I think the following
scheme for dosing and storage is the only way to go. With
this way, one doesn't have to deal with the problems of
crystalization and other things related. Plus, the dry crystals
would be much more prone to potency loss if left dry. If they
are in an alcohol solution, that would be better for
preservation.
As an example, one can start with 20 grams of dried
shrooms. After the filtration of the hot slurry, the resultant
liqueur should be put into an evaporation vessel and with a
fan blowing air across the mouth of the vessel, the liqueur
should be evaportated down to about 50 milliliters. Then, in
a double boiler, heat the small amount of liqueur to put the
crystals and extract back into a cloudy solution. Then while
it is hot, dispense 10 cc of the liqueur into waiting small
storage jars with watertight caps. Each small jar is allowed
to cool, the cap is put on and the jar is placed into the freezer
for storage. Then when it is time to trip, the desired jars are
removed from the freezer, allowed to warm to room temps,
the lids taken off, a small fan set up blowing air across the
jars mouths and the liquere evaporated off to a manageble
"hit". The small jars then become adminstration "spoons" where the entire contents (alcohol - water - and extract) can
be polished off with the tongue.
By Searcher (Novice) on Sunday, December 22, 2002 - 07:46 am:
Almost any liquid will extract something from the shrooms
themselves or the mycelium. Even water will work, producing a brown
syrup that can be dried into a sticky tar. Only the acetone was a bust in
extracting the magic - but it does extract some other crud that might make it
a good pre-wash for more serious extractions. Recapping the results of the
tests using other spirits, 99% isopropyl, 151 proof ethyl alcohol, and 99.9%
methanol - methanol was the hands down winner for getting the crystals.
Once the pretty white crystals have dried, they can be re-dissolved in grain
alcohol for a potent elixer. The crystals tend to absorb water from the air
unless they are kept in a heavily dessicated chamber.
Miscellaneous notes on the methanol: You'll note that this
residue us lighter in color than residue gleaned from the water soaks. Also,
this residue comes out dryer - no intermediate "tar" stage.
An Aqueous-Organic Extraction Method for Isolation and Identification of Psilocin from Mushrooms
J. F. Casale
J. Forens. Sci. 30(1), 247-250 (1985)
Abstract
A simple aqueous extraction method for the isolation and identification of
psilocin from Psilocybe Cubensis mushrooms is reported. This method
employs a dephosphorylation of the phosphate ester to psilocin, which
facilitates a greater product yield and simplifies identification. Psilocin
extracted by this method is sufficiently concentrated and free of cocontaminants to allow identification by infrared spectroscopy and gas
chromatography/mass spectrometry.
The tryptamines are one of four categories of hallucinogenic indoles in
more than 20 classes of indole compounds comprising approximately 600
alkaloids1. Considerable research has been conducted with psilocin and
psilocybin since their isolation by Hofmann et. al.2 Several extraction
techniques1,3-6 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 coextract other compounds such as urea, ergosterol, ergosteral peroxide, α,αtrehalose, baeocystin, and norbaeocystin3,4,7. At present, a useful aqueous
extraction procedure has not been reported for psilocin and psilocybin.
The dephosphorylation of psilocybin to psilocin in vivo has been well
documented1,8,9 and is thought to account for most or all of its central
nervous system activity8. Conversion of psilocybin to psilocin is also
necessary for aqueous extraction with organic solvents because of the very
low lipid solubility of psilocybin. Extraction of only one compound also
permits infrared analysis of the extract.
Concentration and detectability of psilocin and psilocybin are dependent on
several variables, including:
1.
The absence of glucose, which will prevent the production of
psilocybin10.
2.
Low levels of ammonium succinate, which will give poor yields
of psilocybin10.
3.
4.
The growing medium, which requires a pH of less than 710.
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.
Results and Discussion
This method permits rapid isolation of psilocin from hallucinogenic
mushrooms by co-extraction of both psilocin and psilocybin. Dilute acetic
acid is an excellent solvent for this purpose, because both compounds are
very soluble in acetic acid11 and very little of other interfering substances
are extracted, It is most likely some other compounds are co-extracted but
are removed from psilocin in the ether extraction from the aqueous base.
Psilocybin is completely dephosphorytated to psilocin by heating the acid
extract. After addition of the base, extraction into ether should be performed
promptly, because of decomposition of psilocin at a greater pH than 712. The
extraction and dephosporylation steps produce reasonably pure psilocin
from a small amount of mushroom material. Two grams of mushrooms will
often be sufficient to obtain an infrared spectrum of psilocin (Fig. 1).
Smaller mushrooms exhibits provide ample psilocin for mass spectral
analysis (Fig. 2).
This method has been used in our laboratory for six months and has given
excellent results in separating psilocin from methanol-soluble compounds.
Other identification techniques such as gas chromatography and
microcrystalline tests are possible on psilocin extracted by this method.
References
Timing: maximum production of psilocybin occurs on the
seventh day after germination, while maximum production of the
mycelium is reached by the ninth day10.
1.
5.
Temperature: complete loss of psilocin and psilocybin will occur
in harvested mushrooms left at room temperature for an
extended period of time3.
3.
6.
Oxidation: psilocin will oxidize to a blue product (possibly
accounting for the bluing color in the four genera containing
psilocin and psilocybin)9.
Because of the increasing popularity of these mushrooms and kits available
from drug oriented publications for growing mushrooms containing psilocin
and psilocybin in cow manure a simple aqueous extraction procedure has
been developed that extracts reasonably pure psilocin from mature
mushrooms. This extraction method greatly simplifies the identification of
psilocin from those mushrooms by infrared spectroscopy and gas
chromatography/mass spectrometry (GS/MS).
Experimental
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
2.
4.
5.
6.
7.
8.
9.
10.
11.
12.
Schultes, R. E., "Indole Alkaloids in Plant Hallucinogens" Journal of Psychedelic
Drugs, Vol. 8, No. 1, Jan.-March 1976, pp. 7-25.
Hofmann, A., Heim, R., Barck, A., Kobel, H., Frey, A., et al, "Psilicybin [sic] and
Psilocin" Helvetica Chimica Acta, Vol. 42, No. 2, pp. 1557-1572 (1959)
Beug, M. W. and Bigwood, J., "Quantitative Analysis of Psilocybin and Psilocin in
Psilicybe Baeocystis (Singer and Smith) by High-Performance Liquid
Chromatography and by Thin-Layer Chromatography" Journal of Chromatography,
Vol 207, No. 3, pp. 379-385 (1981)
Koike, Y., Wada, K., Kusano, G., Nozoe, S., and Yokoyama, K., "Isolation of
Psilocybin from Psilocybe Argentypes and Its Determination in Specimens of Some
Mushrooms" Journal of Natural Products, Vol. 44, No. 3, May-June 1981, pp. 362365.
Ott, J. and Guzmán, G., "Detection of Psilocybin in Species of Psilocybe Panaeolus
and Psathyrella" Lloydia, Vol. 39, No. 4, July-Aug. 1976, pp. 258-260.
Guzmán, G. and Ott, J., "Description and Chemical Analysis of a New Species of
Hallucinogenic Psilocybe from the Pacific Northwest" Mycologia, Vol. 68, No. 6,
Nov. 1976, pp. 1261-1267.
Lenny, A. W. and Paul, A. G., "Baeocystin and Norbaeocystin: New Analogs of
Psilocybin form Psilocybe Baeocystis" Journal of Pharmaceutical Sciences, Vol. 57,
No. 10, Oct. 1968, pp. 1667-1671.
Horita, A. and Weber, L. J., "Dephosphorylation of Psilocybin in the Intact Mouse"
Toxicology and Applied Pharmacology, Vol. 4, No. 6. Nov. pp. 730-737.
Horita, A. and Weber, L. J., "The Enzymatic Dephosphorylation and Oxidation of
Psilocybin and Psilocin by Mammalian Tissue Homogenates" Biochemical
Pharmacology, Vol. 7, No. 1, 1961, pp. 47-54.
Catalfomo, P. and Tyler, V. E., "The Production of Psilocybin in Submerged Culture by
Psilocybe Cubensis" Lloydia, Vol. 27, No. 1, pp. 53-63 (1964)
Clarke, E. G. C., Isolation and Identification of Drugs, Pharmaceutical Press,
London, 1974, p. 526.
Agurell, S. and Eilsson, L., "Biosynthesis of Psilocybin Part II. Incorporation of
Labeled Tryptamine Derivatives" Acta Chemica Scandinavica, Vol. 22, No. 4, pp.
1210-1218 (1968)
The Psilocybin Production Guide
by Adam Gottlieb 1976
EXTRACTION
Crumble and pulverize the dried mycelial material
and combine each 100 mg of this material with 10
ml of methanol. Place the flask in a hot water bath
for four hours. Filter the liquids with suction
through a filter paper in a buchner funnel with
Celite to prevent clogging. Collect and save the
filtrate liquids. Heat the slurry (the mush in the
filter paper) two more times in methanol as before,
filter, and accumulate the liquids of the three
extractions. To be certain that all of the alkaloids
have been extracted do a small extraction with a
portion of the used slurry and test with Keller's
reagent (glacial acetic acid, ferrous chloride, and
concentrated sulfuric acid). If there is a violet
indication, alkaloids are still present and further
extraction is in order.
In an open beaker evaporate the liquids to total dryness with
a hot water bath or by applying a hair dryer. Be certain that
all traces of methanol have been removed. The remaining
residue should contain 25-50 percent psilocybin/psilocin
mixture. Greater purification can be achieved, but would
require other solvents and chromatography equipment and is
hardly necessary.
Each 100 grams of dried mycelium should yield about 2
grams of extracted material. This should contain at least 500
mg of psilocybin/psilocin mixed or about fifty 10 mg doses.
Theoretically psilocin should have the same effect upon the
user as psilocybin. The only difference between the two is
that the later has a phosphate bond which disappears
immediately after assimilation in the body. In other words, in
the body psilocybin turns into psilocin. Psilocybin is a fairly
stable compound, but psilocin is very susceptible to
oxidization. It is best to keep the extracted material in a dry
air tight container under refrigeration. A sack of silica-gel
can be placed in the container to capture any moisture that
may enter.
DOSAGE
The standard dose of psilocybin or psilocin for a 150 lb
person is a 6-20 mg dose. We will figure the average dose as
10 mg. The crude alkaloid extraction process given here
yields a brownish crystalline powder that is at least 25
percent pure. Each mason jar should contain at least 50
grams of wet mycelium. After drying this would be about 5
grams of material. The crude material extracted from this
should contain 25-30 mg of psilocybin/ psilocin or roughly
2-3 hits. This yield may very to some extent depending upon
several factors. Many of these species contain less of these
alkaloids than dose Psilocybe cubensis and the alkaloidal
content of this species may very in different strains.
Cultivation conditions have alot to do with yield too. Higher
temperatures (75 degrees F.) cause more rapid growth but
lesser psilocybin content than do lower temperatures (70
degrees F.) One must test each new batch of extracted
material to determine the proper distribution of dosages.
Depending on the potency of the mycelia and how well the
extraction was conducted the dose may range between 25
and 100 mg. Also bear in mind that the dose varies for
different individuals.