(Hive Bee)
09-18-03 07:08
No 459761
(Rated as: good read)
URL: http://www.psychedelic-library.org/eleus
Statement:
"If, as we hypothesise in our paper, powdered ergot in water suspension were heated for a time with wood ash, a mildly basic substance containing potassium carbonate, the toxic ergopeptine alkaloids such as ergotamine should be hydrolysed to ergine but not further to lysergic acid. We suggest the use of wood ash as it has always been a very common substance, and thus since time immemorial it must often have been used in trail and error processes of a wide variety. Since ergine is the same ingredient found in the Mexican morning glory whose use by Amerindian shamans - and my own self-testing - leaves little doubt of its psychedelic potency, the possibility that ergot could be processed to yield the same substance seemed the final key to understanding the Kykeon."
Full text:
Mixing the Kykeon
Summary Text of a Presentation Delivered to
The Italian Society for the Study of States Of Consciousness
Perinaldo, Italy, August 29, 2003
By Peter Webster
According to the best information available, the annual autumn celebration at Eleusis in ancient Greece was a most important and spiritually enlightening event, as the writings of a great number of famous names of Greek antiquity testify. [1, 2, 3] The 9-day ceremony known as the Greater Mysteries was one of the most important events of the Greek religious calendar, and it was celebrated every year for nearly two thousand years. No doubt the festivities must have changed and evolved over such an enormous time-span, as did the physical characteristics of the sanctuary where it was practised. Yet the constant and essential use of the sacramental beverage consumed during the final day of the Greater Mysteries, the KYKEON, indicates that it was as necessary to Eleusis as the sacramental bread and wine have been for the two millennia of Christian worship.
The nature and composition of this ancient sacramental potion has concerned many scholars for decades, and centuries. Until recently, the most important thing known about the KYKEON, which literally means "mixture," has perhaps been that no firm conclusions concerning its components or method of preparation could be arrived at. In Greek times, its mystery was always well-preserved by strict rules forbidding any disclosure of what transpired during the final night's celebrations when the KYKEON was drunk, and the secret was also closely guarded by the priests' control over the preparation and use of the sacramental potion. And, with the destruction of the Sanctuary of Eleusis in 395 AD, the priests' secret knowledge was apparently lost forever.
Of one thing we can be sure, however: the KYKEON was not a sacrament in the Christian sense of being merely a symbolic substance. The KYKEON was no placebo, but must surely have had genuine and significant consciousness-enhancing properties that lent themselves to, and reinforced the verbal, visual, doctrinal, and philosophical content of the Eleusinian Mysteries. [1]
It was the longstanding ignorance of the nature of the KYKEON that in 1978 induced Gordon Wasson, Albert Hofmann, and Carl Ruck to publish a new theory concerning Eleusis and its secret sacrament. The principal hypothesis advanced in this work is that the potion of Eleusis, the KYKEON, was a psychoactive preparation made from ergot, a parasitic fungus commonly infesting grains such as rye, wheat, and barley. According to this new and surprising hypothesis, the KYKEON therefore contained lysergic acid alkaloids very similar to LSD. [1]
A recent paper in the journal ELEUSIS by Webster, Perrine and Ruck, also deals with this long-standing question concerning the nature of the KYKEON. The essay was intended to support and extend the ideas first advanced by Albert Hofmann, Gordon Wasson, and Carl Ruck in their book, THE ROAD TO ELEUSIS. Since it was published, criticism of the book's proposals have come from several sources, and our essay MIXING THE KYKEON also served to counter many of these criticisms. [4]
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Illustrated Guide to Lysergic Acid
In order to better understand our hypothesis concerning the KYKEON, some knowledge of the peculiarities of the lysergic acid molecule is necessary. Indeed, much of the criticism of the ideas of THE ROAD TO ELEUSIS has resulted partly from an inadequate knowledge of the chemistry of the ergot alkaloids, and of principles of chemistry in general.
The presentation delivered on August 29 describes in some detail the following aspects and properties of lysergic acid and its amides with the use of a series of diagrams and models projected on-screen.
Lysergic acid and its amide derivatives undergo epimerisation at the carbon at ring position 8 in protonic solvents or under the influence of acidic or basic catalysts to produce the corresponding isolysergic derivatives. The reaction proceeds via an enol intermediate, and is facilitated by the resulting conjugation of the double bonds of the lysergic acid ring system with the enol's double bond from ring position 8 to the side-chain. An equilibrium condition is attained rapidly, or with a delay of several days according to the given conditions and the lysergic acid compound in question, and a characteristic ratio of epimers is produced.[5, 6] The two epimers of a given lysergic acid compound have slightly different physical and chemical properties, and often radically different pharmacological properties. In general, isolysergic acid amides are far less biologically and psychologically active than their lysergic acid epimers.
In addition, the D-ring of lysergic acid compounds may change its conformation from a quasi-chair form, the more stable, to a quasi-boat conformation. Mono-alkyl substituted lysergic acid amides, and lysergamide (ergine), undergo the formation of hydrogen bonds between an amide hydrogen and the nitrogen at ring position 6. This hydrogen bonding may result in an equilibrium between chair and boat forms of a lysergic acid amide such as ergine, or may reinforce the stability of the chair form of an amide such as isoergine, rendering the equilibrium between the two forms to move strongly or entirely to the chair configuration. [7]
As is well known, lysergic acid amides undergo hydrolysis when treated with base in solution to yield lysergic acid. For the reaction to proceed, ergine and other simple amides require a strong base such as potassium hydroxide, high temperatures above 80°C, and an hour or more to complete the process. Ergotamine and other ergopeptine alkaloids, the main constituents of most ergot species, will also hydrolyse to lysergic acid under these conditions, but under milder conditions these compounds do not hydrolyse completely. With a weaker base such as potassium carbonate, and at lower temperatures, ergotamine is partially hydrolysed to ergine. This reaction, apparently long forgotten by chemists, was first discovered in the early research on ergot alkaloids in the 1930s.[8] And it is this process of partial hydrolysis that we propose as the method by which the kykeon was prepared from ergot, converting the toxic ergopeptine alkaloids to ergine and its epimer isoergine.
******
(for part 2 see the following post in this thread)
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(Hive Bee)
09-18-03 07:10
No 459762
A brief overview of "Mixing the Kykeon"
In Albert Hofmann's original conception in THE ROAD TO ELEUSIS, as summarised in our paper, he suggested that the priests of Eleusis might have processed the ergot found in the adjacent barley fields with a simple water extraction. This process would have dissolved off the water-soluble alkaloids ergonovine and methylergonovine while leaving behind the toxic ergopeptine alkaloids such as ergotamine. Ergotamine and other so-called ergopeptine alkaloids found in ergot are dangerously vasoconstrictive and were the agents responsible for the recurring plagues of ergotism known throughout European history. The original theory proposed in THE ROAD TO ELEUSIS thus assumed that the toxic components of ergot were somehow excluded from the KYKEON, and that only the water-soluble alkaloids ergonovine and methyl ergonovine were present. Hofmann had tested ergonovine on himself and found that in doses somewhat larger than the typical doses used in medicine, a definite but weak psychoactive effect resulted. Other tests were far from conclusive, however, and thus arose some significant criticism of Hofmann's proposal.
Much of this criticism was published by Ivan Valencic in the Jahrbuch fur Ethomedizin und Bewusstseinsforschung under the title, "Has the Mystery of the Eleusinian Mysteries Been Solved?" As presented in our paper, these criticisms were:
1 Ergonovine : Psychedelic Potency Weak
The proposed psychoactive ingredients of C. purpurea, ergonovine and methylergonovine, are not exceptionally psychedelic when ingested as synthesised compounds.
2 Actual Ergot Preparations Not Tested
Preparations of Claviceps purpurea itself have not been made and pharmacologically tested which demonstrate it might have been sufficiently psychoactive to have provided the undoubted powerful psychedelic reaction to the kykeon.
3 Side Effects of Discomfort and Lassitude
These same proposed active ingredients, at the doses necessary to produce the moderate psychoactive effects they are capable of producing, also produce significant discomfort, cramping, and lassitude. Presumably the effect of the kykeon was a quite enjoyable experience or it wouldn't have been sought after by rich Athenians to clandestinely entertain guests, nor would the experience of the sacrament at Eleusis have been written about so glowingly by everyone who partook of the Rite and its potion.
4 Side Effect of Possible Spontaneous Abortion
In addition, ergonovine at these higher dose levels is capable of producing spontaneous abortion, and since women were often initiates in the Rite and no such problems were ever described, we must doubt that the full story has been discovered in the C. purpurea hypothesis as advanced in The Road to Eleusis.
5 Ergonovine a Minor and Variable Component of Ergot
In addition to the objections reviewed in our paper, I should now add the fact that ergonovine and methylergonovine are minor and variable components of the alkaloid spectrum in ergot. Thus large quantities of ergot would have been necessary to prepare sufficient water-extract for the multitude of participants, numbering over a thousand in later years. The variability of ergonovine content would also have made the reliability of the preparation uncertain. Yet apparently the KYKEON worked perfectly every year for many centuries.
These would appear to be important reservations. And as Valencic points out in his article, the C. purpurea hypothesis is conspicuously testable, yet the only testing that has been accomplished has not produced very promising results. Note that an overview of several self-experiments with the proposed ergot alkaloids is given in Valencic's article, as well as in part 2 of our paper, "Mixing the Kykeon". Valencic concludes that the ergot hypothesis is not very likely, and he agrees with Robert Graves and Terence McKenna that there exists also a reasonable possibility that psilocybe mushrooms might have helped to produce the astonishment and ecstasy in ancient initiates. Other critical authors have proposed that opium was the active ingredient of the Kykeon, or that it might have been some kind of beer or other fermented product.
The substantial clues to the nature of the Kykeon do not allow us to so easily dismiss the ergot hypothesis however.
Reliability
The celebration at Eleusis was practised every year save one for nearly two thousand years. The Kykeon was used and appreciated at each celebration. Apparently it never failed, so its ingredients must have been constantly available and its method of preparation reliable.
Large Quantities Were Necessary
In later years, a thousand or more participants partook of the Kykeon. As discussed in our paper, the quantities needed and the time of year they must have been collected argues strongly for ergot over alternatives such as Psilocybe mushrooms as suggested by some authors.
Secrecy Maintained
Despite attempts to steal the Kykeon or its recipe such as are documented in the Greek literature, the Eleusis priests nevertheless preserved the Kykeon's secret over the centuries. Thus we may be sure that the active ingredients, or more probably, the method used to prepare the Kykeon was not obvious to outsiders.
The Hymn to Demeter
Barley and Pennyroyal, a type of mint, are specified in the Hymn to Demeter as the constituents of the Kykeon. Although pure barley has no psychoactive properties itself, and pennyroyal at best is only weakly psychoactive, if at all, the reference to barley requires us to explore fully the possibility that parasitic ergot was the essential ingredient.
Two interesting facts are relevant to such an exploration: the spikes of ergot on a grain head such as barley appear to be malformed and discoloured grains of the plant itself, and it must be remembered that it was not until the 19th century that it was generally recognised that ergot was actually an independent parasitic organism, an not merely malformed grains of the cereal host.
It requires no stretch of the imagination, therefore, to believe that the Greeks thought likewise, and that the term "barley" referred to the total harvest, including the "burned and malformed grains" which were actually ergot. Part of the secret maintained by the priests, therefore, would have been that only the malformed grains would have been used to prepare the Kykeon.
Further evidence of this possibility was that Hippocrates, writing in ancient times, recommended barley water for hastening childbirth. Ergot and its alkaloids such as ergotamine, of course, have been used by many down through the ages to hasten childbirth and control post-partum hemorrhage.[9] Only if the "barley" recommended by Hippocrates contained ergot, would his prescription be understandable. Presumably, if Hippocrates had realised that the "malformed barley grains" were actually another organism altogether, and considering his otherwise accurate observations and recommendations on a wide variety of medicinal plants and methods, he would have recommended not barley water but "ergot water" for hastening childbirth.
Some authors have proposed that the barley-mint recipe of the Hymn to Demeter was a total deception devised to keep the true recipe secret. But why would barley and mint have been chosen, and not something more rare and exotic, a proposal that would have made the ruse more believable? If the Hymn to Demeter specifies barley, and there are other references in the Greek literature which implicate barley as well, it would seem that the recipe for the Kykeon must have used barley in some form or other, and that the secret was maintained by virtue of the way in which it was prepared and used.
Ergine and Isoergine
In 1969, I went to Mexico with the intention to study the peyote cactus and ololiuhqui, two visionary plants long used by Central American shamans.
The more potent of the two types of ololiuhqui is of course the common blue morning-glory vine found throughout Mexico, Ipomoea purpurea, and it contains lysergic acid amide, or ERGINE, in a combined form with acetaldehyde.[11] In the course of preparing extracts of ololiuhqui, I tested my preparation to find that its psychoactive properties were quite powerful indeed. When taking a sufficient dose, the effect was quite the equivalent of LSD, except shorter and with some side-effects such stomach cramps.
I was also interested to see if I could prepare some pure lysergic acid from the seed extracts, using the standard procedure of hydrolysis described in the chemical literature on lysergic acid compounds. It was during these researches that I became acquainted with the literature that described the partial hydrolysis of ergotamine to ergine, but only three decades later did I realise the importance of this for the question of the Kykeon of Eleusis. If, as we hypothesise in our paper, powdered ergot in water suspension were heated for a time with wood ash, a mildly basic substance containing potassium carbonate, the toxic ergopeptine alkaloids such as ergotamine should be hydrolysed to ergine but not further to lysergic acid. We suggest the use of wood ash as it has always been a very common substance, and thus since time immemorial it must often have been used in trail and error processes of a wide variety. Since ergine is the same ingredient found in the Mexican morning glory whose use by Amerindian shamans - and my own self-testing - leaves little doubt of its psychedelic potency, the possibility that ergot could be processed to yield the same substance seemed the final key to understanding the Kykeon.
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The conclusions of the presentation
I propose that the epimerisation of lysergic acid amides during the shamanic preparation, or during scientific extraction and analysis, has in some instances not been sufficiently taken into account when trying to understand the ancient use of these substances and modern testing that has attempted to evaluate that use. Likewise, the tendency of some lysergic acid amides to exist in an equilibrium mixture between the chair and boat conformation in ring D - in vivo, as well as in vitro - has also been given insufficient weight in understanding the relative psychoactivity of the various compounds. In the present case, such considerations may help to explain why ergine, taken as a pure compound by a number of investigators, has been assessed as having little or no psychoactivity. [8, 10] Testing of the Aztec shamanic drug ololiuhqui - which contains as its principal alkaloid ergine [11] - has also resulted in claims that the drug is at best unreliable and weak. Yet my own investigations, including self-testing of an extract of ololiuhqui, showed that the equilibrium mixture of ergine and isoergine is quite positively psychedelic and comparable in power but not potency to LSD. Similarly, it is unlikely that ololiuhqui would have attained its formidable reputation among Amerindian shamans if it had little psychoactive effect, for these same shamans had at their disposal a wide range of powerful psychedelics and hallucinogens. Would they have bothered to use, much less hold in high esteem, a plant without similarly powerful effects? Further experiments to be described during the presentation confirm this claim.
I would therefore suggest that the equilibrium mixture of ergine and isoergine resulting from either the partial hydrolysis of ergot or the shamanic preparation of ololiuhqui, is an effective psychedelic preparation, and that it is of greater potency than either compound alone. The equilibrium concentration of ergine to isoergine in aqueous solution is believed to be close to 50/50, and the time required to achieve equilibrium in mild conditions on the order of 1 to 3 hours. Further experimental confirmation of these estimates is needed.
REFERENCES
1. Wasson, Hofmann & Ruck: The Road to Eleusis: Hermes Press 1998.
2. Kerényi: Eleusis: Archetypal Image of Mother and Daughter: Bollingen Series LXV - 4, Princeton University Press 1967.
3. Mylonas: Eleusis and the Eleusinian Mysteries, Princeton University Press 1961.
4. Webster, Perrine, & Ruck: "Mixing the Kykeon": Eleusis, New Series 2000 (4).
5. Stoll & Hofmann: "The Ergot Alkaloids" in Manske, The Alkaloids, Volume VIII: The Indole Alkaloids
6. Stoll et al., Helv. Chim. Acta XXXVII, 2039-2057 (1954)
7. Bernardi & Barbieri: "Ergolene Derivatives VIII - Configuration and Conformation of Lysergamides and Dihydrolysergamides" in Tetrahedron 21, 2539-2551 (1965)
8. Perrine, in Webster, Perrine, & Ruck: "Mixing the Kykeon": Eleusis, New Series 2000 (4).
9. Bové: The Story of Ergot, S. Karger, Basel, 1970, p138
10. Fanchamps: "Some Compounds with Hallucinogenic Activity" in Berde & Schild, Ergot Alkaloids and Related Compounds, Springer-Verlag 1978.
11. Heacock: "Psychotomimetics of the Convolvulaceae" in Progress in Medicinal Chemistry, 11, Ellis & West, editors, North-Holland Publishing Company 1975
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