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Psilocybin

Psilocybin ( 4-phosphoryloxy-N, N-dimethyltryptamine ) is an alkaloid from the tryptamine family; phosphorylated derivative of psilocin ; psychedelic .

Psilocybin
Psilocybn.svg
Psilocybin
Are common
Systematic
name
[3- (2-dimethylaminoethyl) -1 H- indol-4-yl] dihydrogen phosphate
Chem. formulaC 12 H 17 N 2 O 4 P
Physical properties
Molar mass284.25 g / mol
Density1.41 g / cm³
Thermal properties
T. melt.220—228 ° C
T. bale.523.44 ° C
T. ign.270.36 ° C
Classification
Reg. CAS number520-52-5
PubChem
Reg. EINECS number
Smiles
Inchi
RTECS
Chebi
ChemSpider
Security
LD 50285 mg / kg (mice)
280 mg / kg (rat)
12.5 (rabbits)

Chemical formula - C 12 H 17 N 2 O 4 P

From the known biological sources of psilocybin, the greatest amount of it is found in fungi of the genus Psilocybe (hence the name), in smaller quantities - in fungi of the genera ( Panaeolus ), stroparia ( Stropharia ) [1] , Gymnopilus ( Gymnopilus ), fiberglass ( Inocybe ) [2] [3] and in many other mushrooms.

In Russia, a semi-lanceolate psilocybe (Psilocybe semilanceata) containing psilocybin grows.

The chemical structure and effect on human consciousness is similar to dimethyltryptamine. , which is produced in the human body by the endogenously pineal gland .

Mushrooms Psilocybe mexicana are traditionally consumed by Mexican Indians in order to induce a religious and mystical experience .

History

The traditions of the use of psilocybe among various peoples are rooted deep in the past. However, the use of these mushrooms by some Indian tribes in the south of Mexico, in the territory of El Salvador, Guatemala, is best known. Confirmation of this is the numerous finds of 30-centimeter stone sculptures of mushrooms, decorated with the faces of gods and demons, the oldest of them reaches 3,000 years. In the Aztec language, mushrooms were called teonanacatl, which means “flesh of God”, temples were erected to the mushroom gods.

The first written evidence of the use of these mushrooms during festivals, religious ceremonies and magical healing practices is found in the Spanish chroniclers and naturalists of the sixteenth century, who arrived in Mexico shortly after its conquest by Fernando Cortes . The most important of these witnesses is the monk of the Order of St. Francis Bernardino de Sahagun , who mentions magic mushrooms and describes their action and use in several places of his famous historical work, “A General History of Cases in New Spain,” written from 1529 to 1590 [4] .

However, for Europeans, knowledge of mushrooms for a long time remained inaccessible, because the Indians were protected from spread. The decisive role in the discovery of psilocybe was played by the research of Valentina Pavlovna Wasson and her husband R. Gordon Wasson [5] .

Psilocybin was first isolated in pure form in 1958 by Albert Hofmann , a famous scientist who was also involved in the study of psychedelics. The history of isolation and synthesis was described by him in the book “LSD - my problem child” [5] .

Synthesis

Psilocybin is a compound based on the chemical structure of the amino acid tryptophan .

In biosynthesis, psilocybin is derived from tryptamine and is similar to serotonin .

The starting material for the synthesis can be 4-benzyloxyindole , which is converted by the oxalyl chloride method to 4-hydroxy-N, N-dimethyltryptamine ( psilocin ). The latter is esterified with dibenzyl chlorophosphate and, after debenzylation , psilocybin is obtained.

Mechanism of Action

When it enters the intestines, psilocybin, under certain conditions, can be dephosphorylated into psilocin .

 
Psilocin and serotonin

Psilocybin and psilocin have a structure similar to the neurotransmitter serotonin (5-hydroxytryptamine) (a biologically active substance that transmits momentum through the synaptic space between neurons ).

The mechanism of action of psilocybin is not fully understood, but the most likely seems to be an indirect effect on the serotonin receptors 5-HT 2A , to a lesser extent on 5-HT 1A , 5-HT 1D , and 5-HT 2C . However, the substitution of serotonin with psilocybin cannot explain all the effects.

At high dosages, there is a noticeable effect on norepinephrine receptors.

Clinical effects

The effects of psilocybin are comparable to short-lived LSD trips with slight differences.

In amateur circles, the effect of psilocybin subjectively shows increased emotionality compared to LSD and a greater "naturalness" of sensations, sometimes including a religious-mystical experience .

The action of psilocybin lasts approximately 4-7 hours.

In the USA, a series of experiments were conducted at Johns Hopkins University , which, for the first time after the experiments of Timothy Leary with psychedelics in the 1960s, showed that mystical experience can be safely obtained in the laboratory, reports Independent . It was found that the active substance psilocybin contained in hallucinogenic mushrooms caused effects in volunteers identical to those described in religion as a spiritual experience. It also turned out that the action of the substance has a positive effect.

For the experiment, 30 healthy (including mentally) and educated volunteers were selected. The average age was 46 years. None of them had tried hallucinogens before. All of them showed moderate interest in religion. The first time volunteers were given hallucinogenic psilocybin, and two months later, a non-hallucinogenic stimulator, Ritalin . Moreover, in both cases, the participants did not know which drug they were given. During two experiments, which lasted several hours, participants talked about their feelings.

A third of the participants said that drinking psilocybin caused them "the most important spiritual experience in their life." But in general, two-thirds of the participants attributed the effect of psilocybin to the five most significant experiences in their lives. Some compared this experience with the birth of a child or the death of a relative. In addition, after two months, 80% of respondents noted a slight improvement in their health and satisfaction with life, which was also confirmed by a survey of their relatives.

However, a third of the participants experienced panic and paranoia while using psilocybin. Therefore, scientists emphasize the danger of independent experiments with psilocybin. “Never try to do this at home!” Said Roland Griffiths, research director.

Psilocybin is a non-toxic substance. and practically does not cause dependence . Dr. Griffiths suggests that psilocybin can be used to treat addiction, anxiety, and depression. [6]

Depending on the used dose of psilocybin, different exposure levels (plateaus) are achieved :

Level 1. At this level, there is a moderate increase in the perception of colors, musical compositions, and minor memory impairments, mainly short-term ones.

Level 2. A sensation of movement, oscillation (“breathing”) of surrounding objects appears, the colors become extremely bright, saturated, “come to life”. With eyes closed, two-dimensional images of the type of pareidolic appear. There is a sensation of some disturbance in the flow of time, which is apparently associated with violations of short-term memory - time seems to slow down, stretch, reminiscences are noted, a marked increase in creative abilities.

Level 3. Changes in visual perception increase - the surrounding objects look deformed, partially merge with the emerging hallucinatory images. Isolated hallucinations occur. Hallucinations with closed eyes become three-dimensional, the phenomena of synesthesia appear. Distortions in the perception of the current of time increase until the appearance of episodes of the freezing of time, “moments of eternity”. Difficulties in moving can arise (due to the fact that they subjectively require too much effort).

Level 4. Intense hallucinations of transformation, "flow", objects into each other. The feeling of destruction or fragmentation of a person, and parts of it can be projected onto objects, "reviving them." The notion of the existence of time is lost; this concept itself becomes meaningless. The occurrence of phenomena of the type of going beyond the body, the "expansion of consciousness" described by S. Grof when taking LSD, is noted. Synesthesia can spread to several senses.

Level 5. The complete lack of visual contact with the surrounding reality. Total synesthesia. The complete loss of an isolated "I" - there is a feeling of merging with other objects, the surrounding space, the universe. The loss of orientation is so complete that, according to those taking psilocybin in similar doses, in fact, the world consisting of habitually perceived objects and events ceases to exist. Ecstatic experiences like satori , merging with the Universe.

Application

In recent years, some countries have partially lifted a ban on research related to psilocybin. Scientists are increasingly talking about the high potential of this substance in the treatment of mental disorders and the need for further research. In particular, studies by American scientists have confirmed the value of psilocybin for the treatment of severe depression , fear of death, or, conversely, pre-suicidal state, to improve the overall quality of life among cancer patients in the final stages of the disease [7] . There is also evidence of the treatment (prevention of seizures) of migraine and cluster headaches [8] , as well as the treatment of alcoholism [9] [10] . A characteristic feature of psilocybin is the normalizing effect on the psyche in disorders of the opposite nature.

In 2011 (in a placebo-controlled double-blind study), it was shown that the psilocybin experience has a long-term effect on the personality structure, which is expressed in changes in behavior, inclinations and value scale [11] . Prior to this, it was believed that in adults (after 30 years) the core of the personality is practically unchanged, and long-term changes as a result of a single experiment are impossible. The study evaluated changes in neuroticism , extroversion , openness, adequacy, and good faith after a single dose of a high dose of psilocybin. In accordance with individual statements of participants in the experiment on increasing aesthetic perception, imagination and creative abilities, a significant increase in such a personality trait as openness , that is, the ability to adequately accept ideas, situations and lifestyles, even if they are fundamentally new and unusual, was found. Particularly stable changes were observed in people who experienced mystical experiences during the experiment - sensations of a “sacred connection of oneself with all people and objects." Characteristic is a change in human behavior, which depends on inner desire and readiness for such a change - so, shy people after a single use can become more confident, their style of behavior and communication changes.

American scientists found that psilocybin reduced symptoms of depression in 80% of patients with incurable cancer , and another study found that this alkaloid helped patients quit smoking, especially in combination with cognitive-behavioral therapy [12] .

Legal Status

In Russia, psilocybin is included in List I of narcotic drugs, the circulation of which in the Russian Federation is prohibited in accordance with the legislation of the Russian Federation and international treaties of the Russian Federation.

Notes

  1. ↑ The family of stropharia. Genus Psilocybe Archived on May 15, 2012. // Plant Life / Ed. prof. M.V. Gorlenko . - M .: Education, 1976. - T. 2: Mushrooms.
  2. ↑ Nezdoyminogo E.P. Key to mushrooms of Russia. Agaric order. The Spider Web Family. - SPb. : “Science”, 1996. - S. 18-19. - ISBN 5-02-026-035-5 .
  3. ↑ Gartz J. Occurrence of psilocybin, psilocin and baeocystin in Gymnopilus purpuratus // Persoonia. - 1984 .-- T. 14 . - S. 19-22 .
  4. ↑ Sahagun B. de, Kuprienko S.A. General story about the affairs of New Spain. Books X-XI: The knowledge of asteks in medicine and botany / Bernardino de Sahagun, S. A. Kuprienko. - Kiev: Vidavets Kuprіnko S.A., 2013 .-- 218 p. : ill. - (Mesoamerica. Sources. History. Man). ISBN 978-617-7085-07-1
  5. ↑ 1 2 Hofmann, Albert. LSD - My Problem Child. - McGraw-Hill, 1980. - ISBN 0-07-029325-2 .
  6. ↑ Study of the effect of drugs with psilocybin on the state of people with depression (Imperial College London) (neopr.) .
  7. ↑ Psilocybin Advanced Cancer Anxiety Study
  8. ↑ R. Andrew Sewell, MD; John H. Halpern, MD, The Effects of Psilocybin and LSD on Cluster Headache: A Series of 53 Cases Archived March 10, 2010 on Wayback Machine . (eng.)
    Sewell RA, Halpern JH, Pope HG. Response of cluster headache to psilocybin and LSD . Neurology 2006; 66; 1920-1922. ISSN 1526-632X. Abstract Archived November 8, 2006 on the Wayback Machine . (eng.)
  9. ↑ Mangini M. Treatment of alcoholism using psychedelic drugs: a review of the program of research . J Psychoactive Drugs. 1998 Oct-Dec; 30 (4): 381-418. (eng.)
  10. ↑ Hoffer A. Treatment of Alcoholism with Psychedelic Therapy . PSYCHEDELICS, The Uses and Implications of Psychedelic Drugs. 1970. (English)
  11. ↑ Katherine A MacLean, Matthew W Johnson, Roland R Griffiths. Mystical experiences occasioned by the hallucinogen psilocybin lead to increases in the personality domain of openness (Eng.) // Psychopharmacology : journal. - Springer , 2011 .-- November ( vol. 25 , no. 11 ). - P. 1453-1461 . - DOI : 10.1177 / 0269881111420188 .
  12. ↑ Terrien, Alex . Prescription LSD: Can Psychedelics Help Treat Mental Disorders? (English) (July 3, 2018). Date of treatment March 24, 2019.

See also

  • Psilocybe is semi-lanceolate
  • Altered state of consciousness
  • Hallucinogenic mushrooms
  • Psychedelics
  • Dimethyltryptamine
  • LSD

Links

  • Erowid Psilocybin Mushroom Vault (English)
  • FAQ on Psychoactive Indole Derivatives
Source - https://ru.wikipedia.org/w/index.php?title=Psilocybin&oldid=101572987


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Clever Geek | 2019