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The main active component was named psilocybin, and an accompanying alkaloid, was named psilocin.
The dried mushrooms contain 0.2-0.4 per cent of psilocybin. Psilocin is present in trace amounts only. Elucidation of their structures led to the interesting result that these were novel indole derivatives. Degradation studies showed psilocybin to be 4-phosphoryloxy-N, N-dimethyltryptamine. Hydrolysis of psilocybin gave equi-molecular amounts of phosphoric acid and psilocin, which is 4-hydroxy-N, N-dimethyltryptamine (see diagram 1).
Psilocybin is a stable compound which is readily soluble in water and which is obtained in colourless crystals. Psilocin on the other hand is very sensitive to oxidation and difficultly soluble in water. Psilocybin is the first and only hitherto known natural indole compound which has a phosphoric acid radical. Psilocybin and psilocin are also novel in that they are substituted in the 4-position of the indole structure by a hydroxy radical.
These structures were confirmed by synthesis which was carried out by the pathway indicated in the following diagram 2.
The synthetic production of psilocybin is much more rational than obtaining it from the mushrooms.
Later other Psilocybe species belonging to the teonanácatl group were also shown to contain psilocybin, usually together with a small amount of psilocin, e.g ., P. caerulescens Murr. var Mazatecorum Heim, P. Zapotecorum Heim, P. Aztecorum Heim, P. semperviva Heim et Cailleux, Stropharia cubensis Earle ( ). Stropharia cubensis is found not only in Central America but also in Cambodia and Thailand. Furthermore, psilocybin and psilocin were also found in North American Psilocybe species which are not known to be used for magical purposes, namely, in P. pelliculosa A. H. Smith, ( ) P. Cyanescens Wakefield, P. baeocystis Singer and Smith, and in the botanically closely related species Conocybe cyanopus (Atk.) Kuehner ( ).
The availability of the principles of the hallucinogenic mushrooms in the form of pure chemical compounds made it possible to study their pharmacological properties and mental effects.
Mental Effects of Psilocybin
Psilocybin and psilocin produce psychotomimetic effects in man which are similar to those produced by mescaline or LSD-25. The medium oral dose for man is 4 to 8 mg; it elicits the same symptoms as the consumption of about 2 g of dried Psilocybe mexicana fungus ( ,  ).
The first analysis of the effects of psilocybin in man was made at the Psychiatric Clinic of the University of Basle and was based on personal studies made by several members of the staff of the Sandoz Research Laboratories ( ,  ). More detailed investigations have been carried out by Delay and his associates in Paris ( ,  ). As a result of these and many further investigations, of which only a few are mentioned in this article ( ,  ,  ,  ,  ,  ,  ), the effects of psilocybin can be described as follows: Oral doses of a few milligrams lead, after 20 to 30 minutes, to changes in the psychic sphere.
The psychic symptoms produced by small doses, i.e., up to 4 mg, comprise effects on mood and environmental contact in that there frequently is a subjectively pleasant sensation of intellectual and bodily relaxation and detachment from the environment. Not infrequently these effects are associated with a pleasant feeling of physical tiredness and heaviness, but sometimes they are accompanied by a feeling of extraordinary lightness, a bodily hovering. With higher doses, 6 to 20 mg, more profound psychic changes are prominent and are associated with alterations in spatial and temporal perception and with changes in the awareness of the self and body image. Visual hypersensitivity is present and may lead to illusions and hallucinations. In this dreamlike state long-forgotten memories, even some from early childhood, are often recalled.
The psychotomimetic effects of psilocybin, psilocin, LSD, and mescaline were compared by Wolbach et al. ( ) and found to be qualitatively similar. The time course of the psilocybin and psilocin reactions is shorter than that of LSD or mescaline reactions. Psilocin is approximately 1.4 times as potent as psilocybin. This ratio is the same as that of the molecular weights of the two drugs. The development of "cross" tolerance between LSD and psilocybin supports the idea that these two drugs cause psychic disturbances by acting on some common mechanisms, or on mechanisms acting through a common final pathway ( ,  ,  ).
The influence of expectations and mood on responses to psilocybin was studied. It was found that positive expectations, in general, lead to positive experiences; anxiety or preoccupation leads to unpleasant experiences. Mood before the session is the best predictor of mood during the session: unpleasant depressed, anxious moods are intensified on the whole; pleasant moods lead to pleasant and varied experiences. Mystical or religious experiences are often reported after respective expectations and especially when these expectations are combined with high doses. A hypothesis was proposed, according to which the effect of psilocybin is to suspend or deactivate temporarily the cognitive-perceptual screening structures ( ).
The influence of psilocybin on the expressive capabilities for drawing were examined by Roubi èek and Drvota ( ) and by Volmat and Robert ( ).
Pharmacological Properties of Psilocybin
The first study of the effects of psilocybin on the whole animal and on isolated organs was carried out in the Pharmacological Department of Sandoz Ltd. in Basle under the direction of Dr. A. Cerletti.
Psilocybin does not exhibit typical effects on isolated organs (intestine, uterus, heart), with the exception of a pronounced inhibiting effect towards serotonin. On the entire animal, however, it has characteristic autonomic effects, namely, dilatation of the pupils, contraction of the nictitating membrane, piloerection, temperature increase, etc. This is an ergotropic excitation syndrome, which mainly results from a central stimulation of sympathetic structures ( ,  ). In the electroencephalogram an activation may be detected which is characterized by a practically complete disappearance of the slow waves. The electroencephalographic "arousal" reaction of rabbits after psilocybin is not determined by a stimulating effect of the compound on the formatio reticularis but by an inhibition of thalamic substrates ( ,  ). As opposed to this autonomic excitation syndrome produced by the central nervous system, the motor behaviour of the animals in general is strangely rather damped, which, however, does not exclude the simultaneous existence of a certain overexcitation towards outer stimuli.
A very characteristic effect of psilocybin is the regular enhancement of monosynaptic spinal reflexes, e.g., the patellar reflex of cats ( ).
The pharmacological effects of psilocin amply correspond to those of psilocybin qualitatively and quantitatively in studies performed thus far ( ). The phosphoric acid radical, therefore, does not appear to contribute to the pharmacological activity possessed by psilocybin, but as psilocybin is more stable towards chemical influences than psilocin, especially towards oxidation, the phosphoric acid radical could act biologically as a protective group.
The toxicity of psilocybin in animals is very low in comparison to the effective dose in man. The LD 50 for the mouse is 280 mg/kg; i.e., psilocybin is 2.5 times less toxic than mescaline in this test, while it has a 50 times higher psychotomimetic effect in man ( ).
All psilocybin mushrooms contain the same two desired alkaloids,
psilocybin ans psilocin, although they do occur in varying amounts with each
species. Hence, the experiance gained from species will be essentailly the
same as an experience gained from another species. Some variation will be
noted with usage of some of the rarer varieties, but again, the effects will
be essentially the same. Over 16 species of psilocybin mushrooms exist --
only a few are common. One would have to spend many hours in study and
searching the fields to locate and catalogue them all. Only the most common
species need be studied and indentified by the person interested in the
consumption of the mushroom.
The reader has a simple task to preform in order to locate the most
common psilocybin mushroom. He must search cow pastures after rain storms
during those months in which the temperature is between 65 to 85 degress
Fahrenheit. Only those specimens which occur on manure, turn blue when damaged
and have a hollow stem need be considered. There is no chance for error.
The reader is referred to the article by Wasson listed in the
bibliography and to a good library to read about alkaloids. These articles
will enhance your cultural and chemical understanding of the mushroom. Good
-=- CAUTION -=-
Psilocybin mushrooms are against the law. In Louisiana: possession is a
felony. The law-enforcement agencies in some areas are alert to the 'threat'
of a plentiful and naturally-occuring (not to mention exotic) psychedelic.
Consult the Bureau of Dangerous Drugs in your state to find out whether you
are committing a felony or a misdemeasnor. Avoid registering the stock-
reaction "hippie" in the natives of the areas explored. Probably the old guise
of a mycology student will no longer serve.
-=- THE THREE PSILOCYBIN SPECIES COMMON TO THE SOUTH -=-
Of the fifteen domestic species known to contain psilocybin, at least
three are found commonly in the southern United States, from California to
Lousiana and South Carolina to Florida. One of these, the Ps. cubensis and
Panaeolus subbalteatus will be found in the same area as they all grow on
manure. The Amanita muscaria (Mexico's 'magic' mushroom) a psilocybin
mushroom, is also noted below, because it is sometimes found in the woodland
areas of the U.S. South. A reference is made in the bibliography to a fine
article on the mushroom-cult of Mexico.
-=- SETTING OUT MUSHROOM HUNTING -=-
Your first trip need not be elaborate. The author has found an ample
supply of Ps. cubensis growing within a 50 mile radius of New Orleans. For
your first trip, it may be best to select a site close to home. You can
increase your range after you have learned to identify them. The psilocybin
mushrooms described in this guide, like many mushrooms, may be found in
greatest quantity in a well-drained or sloped area.
The Ps. cubensis and Panaeolus subbalteatus grow only on cow, horse, pig,
sheep or even goat manure (all grass or grain fed animals) or soil that has
been enriched with manure. They grow most commonly on cow manure. The Ps.
caerulescens grow on stream or river banks. All species grow at temperatures
between 45 and 85 degrees Fahrenheit. They prefer a well-drained site because
the immature mycellium is damaged by an excess of water. The mature mycellium,
however, demands a large quantity of water for maximum production. The
mycellium is the stage of the fungus that produces the mushroom. It is
germinated from the spores and grows, permeating the soil or manure. It looks
like a moldish web-like growth and maay take from 6 to 12 weeks to longer to
The mushroom, the actual fruit, is grown under the soild and with time
and proper moisture pops up and appears to grow extremely fast. In the case of
the Ps. cubensis, the fruit matures in 24 hours. Therefore, check the weather
reports for frontal systems bringing cool air and rain. These conditions,
especially in late spring and early fall (but not during the hot summer
months) are excellent for mushroom growth. Less psilocybin is produced during
hot weather. Even if you do get a good rain during a long hot spell, the poor
quality of the few specimens you might find makes them harly worth taking.
Also, an excess of that other vital ingredient, water, will cause the
mycellium to rot. The mycellium can handle a few inches of rain on one day and
even a few inches a day for several days, but over a prolonged period of time
it will die back and become sickly. The warm dry summer promotes the growth of
the mycellium, and a cool, moist fall will bring forth the mushrooms in
plentiful numbers. The sun quickly causes those mushrooms left growing in the
field to age and rot because they are over 90% water.
If picked freshly, however, the mushroom will retain its potency for
years, provided they are not sealed in an air-tight container, which causes
them to rot in thier own residual water content. The air-dried shrivelled
mushrooms may be stored for future delectation.
-=- A WARNING -=-
It is well known that a few species of the non-psilocybin mushrooms are
dangerously poisionous. Ingestion will cause the body to flush itself through
the bowels and by vomiting, with extreme cramps varying from mild to severe
discomfort to death. For this reason, not even a tiny piece of any mushroom
collected by the beginner should be eaten in the field. First compare the
fresh mushrooms to the descriptions and photographs herein. The descriptions
are calculated to be exhaustive; even so, when you are certain that you have
a specimen of one of the described species, refrain from eating or smoking
more than a tiny bite.
The person sensitive to other drugs, such as grass or LSD, will be able
tell whether the desired substance is present; a person not so sensitive will
still feel something. You will also be able to determine whether the species
you have collected (be it not psilocybin) is poisonous or not. Six of the
eight alkaloids present in the chemical structure of the psilocybin mushroom
are toxic (the two other are psilocybin and psilocin). From this mild
toxicity, a slight queasiness of the stomach may resulty. Also, even if the
beginner has happened on a genuine psilocybin mushroom, the eating of it in
the field may result in lack of interest in the further work of collecting,
with the consequent loss of many pounds of muchrooms which he might otherwise
have collected and dried.
The famed 'magic' mushroom of Mexico, the Amanita muscaria, causes
intense hallucinations and is therefore well sought after, but a word of
caution is in order. The A. muscaria is a highly toxic mushroom. It contains
yet more poisonous alkaloids. It should be avoided as ingestion of more than
a few specimens can cause illness and possibly death. The other common species
listed in this book are all safe and non-poisonous. The A. muscaria is a red
ball-shaped mushroom. It is very distinct and bears not the least resemblance
to any of the three species catalogued in this text.
-=- IDENTIFICATION PROLOGUE -=-
All of the psilocybin species described herein may be most conclusively
identified by an enzyme that occurs with the psilocybin. This enzyme turns
blue thru an oxidation process after the flesh of the mushroom is damaged.
Crack the stem to check for the reaction, which takes from 20 to 120 minutes
to occur. The blue is similar to blue ink, unless the flesh of the mushroom is
yellowish, in which case the color will appear blue-green. All psilocybin
mushrooms (with the exception of one uncommon species that is not covered in
this manual) turn blue in this manner. A few chemicals will speed up the
oxidation/bluing process but are not readily available. Because these
chemicals are unstable and are difficult to work with, to hassle with them in
the field, for most people, is not worth the trouble.
This natural bluing-reaction noted in the psilocybin species is also
noted in one other non-psychedelic genus. To even the least observant person
the difference in physical appearance is extremely obvious. The non-psilocybin
mushrooms that turn blue are: large, bulbous and usually very smooth. This
fat cap cannot be confused with the psilocybin cap. The cap and stem will be
yellow or yellow-brownish evenly over the entire surface. With age, the
specimens of this genus may be noted to turn blue on parts of the stem. The
underside of the cap has pores instead of gills. These pores, appearing as an
organic sponge, will be of the same color-range. The stem is proportioned like
the cap and is quite solid and fleshy. These species do not occur on dung but
may be located in pastures and lawns after rains.
Psilocybin Mushroom Chemistry
NAME : Psilocybin
CHEMICAL NAME : 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol dihydrogen phosphate ester
ALTERNATE CHEMICAL NAMES : O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine; Indocybin
CHEMICAL FORMULA C12H17N2O4P
MOLECULAR WEIGHT 284.25
MELTING POINT 220-228° C (Crystals from boiling water)
MELTING POINT 185-195° C (Crystals from methanol)
pH 5.2 (in 50% aq ethanol)
LD50 285 mg/kg i.v.(mice)
LD50 280 mg/kg i.v. (rats)
LD50 12.5 mg/kg i.v.(rabbits)
From the Merck Index 12th Edition
NAME : Psilocin
CHEMICAL NAME : 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol
ALTERNATE CHEMICAL NAMES : 4-hydroxy-N,N-dimethyltryptamine; psilocyn
CHEMICAL FORMULA C12H16N2O
MOLECULAR WEIGHT 204.27
MELTING POINT 173-176° C (plates from methanol)
From the Merck Index 12th Edition