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By contrast, the synthesis of psilocybin, ..

In the 1962 , which was run by Pahnke at the under the supervision of Timothy Leary, almost all of the graduate degree student volunteers who received psilocybin reported profound religious experiences. One of the participants was religious scholar , author of several textbooks on ; he later described his experience as "the most powerful cosmic homecoming I have ever experienced." In a 25-year followup to the experiment, all of the subjects given psilocybin described their experience as having elements of "a genuine mystical nature and characterized it as one of the high points of their spiritual life". Psychedelic researcher considered the study partially flawed due to incorrect implementation of the double-blind procedure, and several imprecise questions in the mystical experience questionnaire. Nevertheless, he said that the study cast "a considerable doubt on the assertion that mystical experiences catalyzed by drugs are in any way inferior to non-drug mystical experiences in both their immediate content and long-term effects". This sentiment was echoed by psychiatrist William A. Richards, who in a 2007 review stated "[psychedelic] mushroom use may constitute one technology for evoking revelatory experiences that are similar, if not identical, to those that occur through so-called spontaneous alterations of brain chemistry."A group of researchers from led by Griffiths conducted a study to assess the immediate and long-term psychological effects of the psilocybin experience, using a modified version of the mystical experience questionnaire and a rigorous double-blind procedure. When asked in an interview about the similarity of his work with Leary's, Griffiths explained the difference: "We are conducting rigorous, systematic research with psilocybin under carefully monitored conditions, a route which Dr. Leary abandoned in the early 1960s." The -funded study, published in 2006, has been praised by experts for the soundness of its experimental design. In the experiment, 36 volunteers without prior experience with hallucinogens were given psilocybin and (Ritalin) in separate sessions; the methylphenidate sessions served as a and psychoactive . The degree of mystical experience was measured using a questionnaire developed by Ralph W. Hood; 61% of subjects reported a "complete mystical experience" after their psilocybin session, while only 13% reported such an outcome after their experience with methylphenidate. Two months after taking psilocybin, 79% of the participants reported moderately to greatly increased life satisfaction and sense of well-being. About 36% of participants also had a strong to extreme "experience of fear" or (i.e., a "bad trip") at some point during the psilocybin session (which was not reported by any subject during the methylphenidate session); about one-third of these (13% of the total) reported that this dysphoria dominated the entire session. These negative effects were reported to be easily managed by the researchers and did not have a lasting negative effect on the subject's sense of well-being.

Improvements to the Synthesis of Psilocybin

The nature and the course of this extraordinary disturbance raised my suspicions that some exogenic intoxication may have been involved and that the Iysergic acid diethylamide with which I had been working that afternoon could have been responsible. I had separated the two isomeric forms that are formed by this synthesis, namely Iysergic diethylamide and isolysergic acid diethylamide and prepared the crystalline water soluble salt of Iysergic acid diethylamide with tartaric acid. However, I could not imagine how this compound could have accidentally found its way into my body in a sufficient quantity to produce such phenomena. Moreover, the nature of the symptoms did not tally with those previously associated with ergot poisoning. In order to get to the root of the matter, I decided to conduct some experiments on myself with the substance in question. I started with the lowest dose that might be expected to have any effect, i.e., 0.25 mg LSD. The notes in my laboratory journal read as follows:

Improvements to the Synthesis of Psilocybin ..

the synthesis of psilocybin, ..

In the early 1960s, became a testing ground for psilocybin, through the efforts of and his associates and Richard Alpert (who later changed his name to ). Leary obtained synthesized psilocybin from Hofmann through Sandoz pharmaceutical. Some studies, such as the , suggested promising results using psilocybin in . According to a 2008 review of safety guidelines in human hallucinogenic research, however, Leary and Alpert's well-publicized termination from Harvard and later advocacy of hallucinogen use "further undermined an objective scientific approach to studying these compounds". In response to concerns about the increase in unauthorized use of psychedelic drugs by the general public, psilocybin and other hallucinogenic drugs suffered negative press and faced increasingly restrictive laws. In the United States, laws were passed in 1966 that prohibited the production, trade, or ingestion of hallucinogenic drugs; Sandoz stopped producing LSD and psilocybin the same year. Further backlash against LSD usage swept psilocybin along with it into the Schedule I category of illicit drugs in 1970. Subsequent restrictions on the use of these drugs in human research made for such projects difficult to obtain, and scientists who worked with psychedelic drugs faced being "professionally marginalized".Despite the legal restrictions on psilocybin use, the 1970s witnessed the emergence of psilocybin as the "entheogen of choice". This was due in large part to a wide dissemination of information on the topic, which included works such as those by author , and several books that taught the technique of growing psilocybin mushrooms. One of the most popular of this latter group was published in 1976 under the pseudonyms O.T. Oss and O.N. Oeric by Jeremy Bigwood, , K. Harrison McKenna, and , entitled . Over 100,000 copies were sold by 1981. As ethnobiologist explains, "These authors adapted San Antonio's technique (for producing edible mushrooms by casing cultures on a rye grain substrate; San Antonio 1971) to the production of . The new technique involved the use of ordinary kitchen implements, and for the first time the layperson was able to produce a potent entheogen in his own home, without access to sophisticated technology, equipment or chemical supplies."

American banker and amateur and his wife Valentina studied the ritual use of psychoactive mushrooms by the native population in the village . In 1957, Wasson described the psychedelic visions that he experienced during these rituals in "", an article published in the popular American weekly magazine. Later the same year they were accompanied on a follow-up expedition by French mycologist , who identified several of the mushrooms as species. Heim cultivated the mushrooms in France, and sent samples for analysis to , a chemist employed by the Swiss multinational pharmaceutical company Sandoz (now Novartis). Hofmann, who had in 1938 created , led a research group that isolated and identified the psychoactive compounds from . Hofmann was aided in the discovery process by his willingness to ingest mushroom to help verify the presence of the active compounds. He and his colleagues later a number of compounds chemically related to the naturally occurring psilocybin, to see how changes would affect psychoactivity. The new molecules differed from psilocybin in the position of the or group at the top of the , and in the numbers of groups (CH3) and other additional s. Two diethyl (containing two groups in place of the two methyl groups) of psilocybin and psilocin were synthesized by Hofmann: , called CEY-19, and , called CZ-74. Because their physiological effects last only about three and a half hours (about half as long as psilocybin), they proved more manageable in European clinics using "psycholytic therapy"—a form of involving the controlled use of psychedelic drugs. Sandoz marketed and sold pure psilocybin under the name Indocybin to physicians and clinicians worldwide. There were no reports of serious complications when psilocybin was used in this way.

Konstitutionsaufklärung und Synthese von Psilocybin

This structure was confirmed by total synthesis.

The only report of chemical studies on the seeds of mentioned in Schultes' review on ololiuqui is that of the pharmacologist Santesson in Stockholm in 1937. He was, however, unsuccessful in isolating definite crystalline compounds. Alcoholic extracts produced a kind of narcosis or partial narcosis in frogs and mice.
In 1955, the Canadian psychiatrist Osmond conducted a series of experiments on himself. After taking 60 to 100 Rivea seeds he passed into a state of apathy and listlessness accompanied by increased visual sensitivity. After about four hours, there followed a period in which he had a relaxed feeling of well-being that lasted for a rather longer time. In contrast to these results, KinrossWright in 1958 published experiments performed on eight male volunteers who had taken doses of up to 125 seeds without any ascertainable effect.
After the chemical investigations of the sacred Mexican mushrooms had been successfully brought to a close, I decided to tackle the problem of the third Mexican magic drug, ololiuqui. Through the help of R. G. Wasson, I was able to obtain authentic ololiuqui from a Zapotec Indian near Oaxaca in southern Mexico. One sample consisted of brown seeds, which proved on botanical classification to stem from The black seeds of the second sample were identical with those of (syn. These black seeds, called "badoh negro," arc used especially in the region of the Zapotecs, in conjunction with, or instead of "Badoh," the brown seeds of
The chemical analysis of the ololiuqui seeds gave a quite surprising result. The psychotomimetic principles that we isolated proved to be Iysergic acid derivatives, Iysergic acid amides and other ergot alkaloids. Thus in this strange Mexican drug we met with old friends, since Iysergic acid derivatives and ergot alkaloids had been favorite subjects of research in our laboratory since the time I had first synthesized LSD in the nineteen-thirties.

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,

A method for the large-scale synthesis of psilocybin was reported by a Japanese group in 2003
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von Psilocybin" [The composition and synthesis of psilocybin].

IT IS OFTEN STATED in the literature that LSD was discovered by chance. The following account will show that LSD was not the fruit of a chance discovery, but the outcome of a more complex process that had its beginnings in a definite concept, and was followed up by appropriate experiments, during the course of which a chance observation served to trigger off a planned investigation, which then led to the actual discovery. Such a train of events often underlies what is said to be a chance discovery.
I prepared lysergic acid diethylamide for the first time in 1938 as part of a systematic chemical and pharmacological investigation of partially synthetic amides of Iysergic acid in the Sandoz pharmaceutical-chemical research laboratories in Basle, headed at that time by Professor Arthur Stoll. Lysergic acid is the characteristic nucleus of the alkaloids of ergot and can be obtained by alkaline hydrolysis of these alkaloids. Using a newly developed procedure, one had proved it possible to combine Iysergic acid with amines in peptide linkage. In this way, the specific oxytocic principle of ergot, namely Ergometrine, known in this country as ergonovine, was produced. This was the first partial synthesis of a natural ergot alkaloid, and by modifying the alkanolamine side chain of Ergometrine a new synthetic derivative, which we named Methergine, was obtained. In its pharmacological properties Methergine proved to be superior to the natural alkaloid, and today it is used throughout the world in obstetrics for the arrest of hemorrhage. Although interest centered mainly on oxytocic and hemostatic activity in these investigations, the new method of synthesis was also employed to prepare amides of Iysergic acid, which, on the basis of their chemical structure, might be expected to possess different pharmacological properties. Thus among other compounds, I synthesized the diethylamide of Iysergic acid with the intention of obtaining an analeptic. This compound might have been expected to possess analeptic properties because of its structural relationship with the well-known circulatory stimulant nikethamide.

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