Synthesis of Psilocybin & Psilocin - Lycaeum

The final proof of the correctness of the proposed structures was provided by the total synthesis of psilocin and psilocybin. The synthetic production of psilocybin and psilocin is now more economical than obtaining them from the mushrooms. My colleagues who participated in these investigations were: Dr. Arthur Brack, Dr. Albert Frey, Dr. Hans Kobel, Dr. Hans Ott, Dr. Theodor Petrzilka and Dr. Franz Troxler.
A review of the historical, ethnological, botanical and chemical aspects of the hallucinogenic Mexican mushrooms is presented in the beautiful volume, by Roger Heim and R. Gordon Wasson, edited by the Museum National d'Histoire Naturelle in Paris. An average human oral dose of psilocybin is 6 mg to 10 mg. Psilocin possesses similar activity. This means that psilocybin and psilocin are about 100 times more active than mescaline and about 100 times less active than LSD. But there is no significant difference between the two compounds in quality of hallucinogenic activity. The development of cross-tolerance between LSD and psilocybin lends support to the view that these two drugs cause psychic disturbances by acting on some common mechanism, or on mechanisms acting through a common final pathway.
When I was in Mexico on an expedition with my friend Gordon Wasson in 1963, in search of a hallucinogenic plant, we also visited the famous curandera Maria Sabina in Huautla de Jimenez. We were invited to attend a nocturnal mushroom ceremony in her hut, but as it was late in the year and no more mushrooms were available, I supplied her with pills containing synthetic psilocybin. She took a rather strong dose corresponding to the number of mushrooms she usually ingests. It was a gala performance assisted by a number of people of Maria Sabina's clan. At dawn when we left the hut, our Mazateca interpreter told us that Maria Sabina had said there was no difference between the pills and the mushrooms. This was a final proof that our synthetic psilocybin was identical in every respect with the natural product.
That was the story of the second magic Mexican drug of teonanacatl. But there was still the riddle of ololiuqui, the third magic Mexican drug. Ololiuqui is the Aztec name for the seeds of certain convolvulaceous plants that since prehispanic times have been used by the Aztecs and related tribes in their religious ceremonies and magic medicinal practices in the same way as the sacred mushrooms and the cactus peyotl. Ololiuqui is still used in our day by such tribes as the Zapotecs, Chinantecs, Mazatecs, and Mixtecs, who live in the remote mountains of southern Mexico in comparative isolation, little influenced by Christianity. An excellent review of the historical, ethnological and botanical aspects of the ololiuqui question was given in 1941 by R. Evans Schultes of the Botanical Museum at Harvard, in his monograph,

Erowid Psilocybin & Psilocin Vault

In the body psilocybin is dephosphorylated rapidly to psilocin by phosphatase [3] .

Dr. Albert Hofmann | Psilocybin | Psilocin

The first magic plant to be studied scientifically was peyotl, also named peyote; this was under investigation as early as at the turn of the century. The history of peyotl, its ancient cultic use by the Indians of Central America and its present use, as well as the psychic effects on human beings, were first described by Louis Lewin, the brilliant pharmacologist and toxicologist, in his classic monograph entitled
Lewin established the basis for psychotomimetic research by this standard publication in which the psychotomimetics or hallucinogens, named by him were characterized and grouped for the first time in an independent group within the psychopharmaceutical drugs. The peyotl cactus was named by the botanist Hennings in honor of Lewin. Louis Lewin and Arthur Heffter, who isolated the alkaloid mescaline in 1896 from the cactus, deserve a place of honor in the history of psychopharmacological psychotomimetic research. In 1919, Ernst Späth in Vienna succeeded in elucidating the chemical structure of mescaline and in synthesizing this alkaloid.
Mescaline made it possible for the first time to investigate the phenomenon of hallucinogenic effects from a scientific, pharmacological, and clinical aspect using a pure chemical compound. The results of this first period of psychopharmacological investigations in the nineteen twenties were published in the classical monograph by K. Beringer. However, in the years to follow, interest in hallucinogenic research faded. Not until the nineteen forties with the discovery of LSD did this line of research receive a new impetus leading to an upsurge of interest that has lasted until the present time.
Our preoccupation with LSD was the reason why the second magic drug of Mexico, teonanacatl, which means "sacred mushroom," was submitted to our laboratory for a chemical analysis. The use and worship of teonanacatl by the Indians of Central America must be very ancient. In Guatemala, "mushroom stones" have been found the oldest specimens of which are over three thousand years old.

Dr. Albert Hofmann, the father of LSD, psilocybin, and psilocin.

The delivery was of heroin, cocaine, hashish, marijuana, methamphetamine, LSD, psilocybin or psilocin and was for consideration (meaning sold rather than shared / given away);

Psilocin is extracted at a much slower rate than is psilocybin because it is contained intracellularly in the plant, and thus slower to be gotten out.
Ten grams or more of a mixture or substance containing a detectable amount of psilocybin or psilocin; or

Shroomery - Psilocybin and Psilocin

Mescaline, being a phenylethylamine derivative, is structurally related to the neurohumoral transmitters norepinephrine and epinephritic. LSD, and the constituents of ololiuqui as well as the active principles of the hallucinogenic mushrooms psilocybin and psilocin, are indoles, more precisely tryptamine derivates, like the neurohumoral factor serotonin. Because of this structural relationship between the hallucinogens and norepinephrine and serotonin, it is probable that the psychotomimetic activity is due to an interaction between these substances in the metabolism of the central nervous system. Investigation of the relationships between endogenous neurohumoral factors and hallucinogens is a rewarding facet of psychopharmacological research.
As I am a chemist, I have mainly discussed the chemical, phytochemical and historical aspects of the discovery of LSD and the investigation of naturally occurring hallucinogens. Needless to say, this audience attaches primary importance to the pharmacological and clinical effects, which make LSD and the other specific hallucinogens a valuable tool in experimental psychiatry and a valuable drug aid in psychoanalysis and psychotherapy. Another aspect of the hallucinogens and especially of LSD with enormous social impact is of course the paramedical use and the misuse of these substances. But this very complex problem would provide material for a special lecture, or indeed for a series of such lectures.
The aim of my chapter is to describe an unusual cycle of chemical research, full of coincidences, a kind of magic circle, which started with the synthesis of various Iysergic acid amides and the discovery of the extraordinary psychotomimetic potency of Iysergic acid diethylamide (LSD), which led to the investigation of the sacred Mexican mushrooms, the isolation of psilocybin, and ended with ololiuqui, where lysergic acid amides were again encountered, thus closing the magic circle.

Apparently the enzymes that are responsible for the 4-hydroxy group of psilocin are indifferent to what it is they choose to 4-hydroxylate.

Other - Synthesizing DMT from psilocin ..

He has taken things like DPT or DIPT and put them in the growth media and the fruiting bodies that came out contain 4-hydroxy-DPT or 4-hydroxy-DIPT instead of psilocin.

Synthesis, hydrolysis and stability of psilocin glucuronide

I'll give you even odds that if you put spores of a species on cow droppings loaded with 5-MeO-DMT you would come out with mushrooms containing 4,5-HO-MeO-DMT.