The Magic Morning Glory Ololiuhqui

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After we had managed to solve the riddle of the sacred mushroom teonanacatl in a relatively short time, I also became interested in the problem of another Mexican magic drug not yet chemically elucidated, ololiuhqui. Ololiuhqui is the Aztec name for the seeds of certain climbing plants (Convolvulaceae) that, like the mescaline cactuspeyotl and the teonanacatl mushrooms, were used in pre-Columbian times by the Aztecs and neighboring people in religious ceremonies and magical healing practices. Ololiuhqui is still used even today by certain Indian tribes like the Zapotec, Chinantec, Mazatec, and Mixtec, who until a short time ago still led a genuinely isolated existence, little influenced by Christianity, in the remote mountains of southern Mexico.

An excellent study of the historical, ethnological, and botanical aspects of ololiuhqui was published in 1941 by Richard Evans Schultes, director of the Harvard Botanical Museum in Cambridge, Massachusetts. It is entitled "A Contribution to Our Knowledge of Rivea corymbosa, the Narcotic Ololiuqui of the Aztecs." The following statements about the history of ololiuhqui derive chiefly from Schultes's monograph. [Translator's note: As R. Gordon Wasson has pointed out, "ololiuhqui' is a more precise orthography than the more popular spelling used by Schultes. See Botanical Museum Leaflets Harvard University 20: 161-212, 1963.]

The earliest records about this drug were written by Spanish chroniclers of the sixteenth century, who also mentioned peyotl and teonanacatl. Thus the Franciscan friar Bernardino de Sahagun, in his already cited famous chronicle Historia General de las Cosas de Nueva Espana, writes about the wondrous effects of ololiuhqui: "There is an herb, called coatl xoxouhqui (green snake), which produces seeds that are called ololiuhqui. These seeds stupefy and deprive one of reason: they are taken as a potion."

We obtain further information about these seeds from the physician Francisco Hernandez, whom Philip II sent to Mexico from Spain, from 1570 to 1575, in order to study the medicaments of the natives. In the chapter "On Ololiuhqui" of his monumental work entitled Rerum Medicarum Novae Hispaniae Thesaurus seu Plantarum, Animalium Mineralium Mexicanorum Historia, published in Rome in 1651, he gives a detailed description and the first illustration of ololiuhqui. An extract from the Latin text accompanying the illustration reads in translation: "Ololiuhqui, which others call coaxihuitl or snake plant, is a climber with thin, green, heart-shaped leaves The flowers are white, fairly large The seeds are roundish. . . . When the priests of the Indians wanted to visit with the gods and obtain information from them, they ate of this plant in order to become inebriated. Thousands of fantastic images and demons then appeared to them " Despite this comparatively good description, the botanical identification of ololiuhqui as seeds of Rivea corymbosa (L.) Hall. f. occasioned many discussions in specialist circles. Recently preference has been given to the synonym Turbina corymbosa (L.) Raf.

When I decided in 1959 to attempt the isolation o the active principles of ololiuhqui, only a single report on chemical work with the seeds of Turbina corymbosa was available. It was the work of the pharmacologist C. G. Santesson of Stockholm, from the year 1937. Santesson, however, was not successful in isolating an active substance in pure form.

Contradictory findings had been published about the activity of the ololiuhqui seeds. The psychiatrist H. Osmond conducted a self-experiment with the seeds of Turbina corymbosa in 1955. After the ingestion of 60 to 100 seeds, he entered into a state of apathy and emptiness, accompanied by enhanced visual sensitivity. After four hours, there followed a period of relaxation and well-being, lasting for a longer time. The results of V. J. Kinross-Wright, published in England in 1958, in which eight voluntary research subjects, who had taken up to 125 seeds, perceived no effects at all, contradicted this report.

Through the mediation of R. Gordon Wasson, I obtained two samples of ololiuhqui seeds. In his accompanying letter of 6 August 1959 from Mexico City, he wrote of them:

. . . The parcels that I am sending you are the following: . . .

A small parcel of seeds that I take to be Rivea corymbosa, otherwise known as ololiuqui well-known narcotic of the Aztecs, called in Huautla "la semilla de la Virgen." This parcel, you will find, consists of two little bottles, which represent two deliveries of seeds made to us in Huautla, and a larger batch of seeds delivered to us by Francisco Ortega "Chico," the Zapotec guide, who himself gathered the seeds from the plants at the Zapotec town of San Bartolo Yautepec

The first-named, round, light brown seeds from Huautla proved in the botanical determination to have been correctly identified as Rivea (Turbina) corymbosa, while the black, angular seeds from San Bartolo Yautepec were identified as Ipomoea violacea L.

While Turbina corymbosa thrives only in tropical or subtropical climates, one also finds Ipomoea violacea as an ornamental plant dispersed over the whole earth in the temperate zones. It is the morning glory that delights the eye in our gardens in diverse varieties with blue or blue-red striped calyxes.

The Zapotec, besides the original ololiuhqui (that is, the seeds of Turbina corymbosa, which they call badoh), also utilize badoh negro, the seeds of Ipomoea violacea. T. MacDougall, who furnished us with a second larger consignment of the last-named seeds, made this observation.

My capable laboratory assistant Hans Tscherter, with whom I had already carried out the isolation of the active principles of the mushrooms, participated in the chemical investigation of the ololiuhqui drug. We advanced the working hypothesis that the active principles of the ololiuhqui seeds could be representatives of the same class of chemical substances, the indole compounds, to which LSD, psilocybin, and psilocin belong. Considering the very great number of other groups of substances that, like the indoles, were under consideration as active principles of ololiuhqui, it was indeed extremely improbable that this assumption would prove true. It could, however, very easily be tested. The presence of indole compounds, of course, may simply and rapidly be determined by colorimetric reactions. Thus even traces of indole substances, with a certain reagent, give an intense blue-colored solution.

We had luck with our hypothesis. Extracts of ololiuhqui seeds with the appropriate reagent gave the blue coloration characteristic of indole compounds. With the help of this colorimetric test, we succeeded in a short time in isolating the indole substances from the seeds and in obtaining them in chemically pure form. Their identification led to an astonishing result. What we found appeared at first scarcely believable. Only after repetition and the most careful scrutiny of the operations was our suspicion concerning the peculiar findings eliminated: the active principles from the ancient Mexican magic drug ololiuhqui proved to be identical with substances that were already present in my laboratory. They were identical with alkaloids that had been obtained in the course of the decades-long investigations of ergot; partly isolated as such from ergot, partly obtained through chemical modification of ergot substances.

Lysergic acid amide, lysergic acid hydroxyethylamide, and alkaloids closely related to them chemically were established as the main active principles of ololiuhqui. (See formulae in the appendix.) Also present was the alkaloid ergobasine, whose synthesis had constituted the starting point of my investigations on ergot alkaloids. Lysergic acid amide and lysergic acid hydroxyethylamide, active principles of ololiuhqui, are chemically very closely related to lysergic acid diethylamide (LSD), which even for the non-chemist follows from the names.

Lysergic acid amide was described for the first time by the English chemists S. Smith and G. M. Timmis as a cleavage product of ergot alkaloids, and I had also produced this substance synthetically in the course of the investigations in which LSD originated. Certainly, nobody at the time could have suspected that this compound synthesized in the flask would be discovered twenty years later as a naturally occurring active principle of an ancient Mexican magic drug.

After the discovery of the psychic effects of LSD, I had also tested lysergic acid amide in a self-experiment and established that it likewise evoked a dreamlike condition, but only with about a tenfold to twenty-fold greater dose than LSD. This effect was characterized by a sensation of mental emptiness and the unreality and meaninglessness of the outer world, by enhanced sensitivity of hearing, and by a not unpleasant physical lassitude, which ultimately led to sleep. This picture of the effects of LA-111, as lysergic acid amide was called as a research preparation, was confirmed in a systematic investigation by the psychiatrist Dr. H. Solms.

When I presented the findings of our investigations on ololiuhqui at the Natural Products Congress of the International Union for Pure and Applied Chemistry (IUPAC) in Sydney, Australia, in the fall of 1960, my colleagues received my talk with skepticism. In the discussions following my lecture, some persons voiced the suspicion that the ololiuhqui extracts could well have been contaminated with traces of lysergic acid derivatives, with which so much work had been done in my laboratory.

There was another reason for the doubt in specialist circles concerning our findings. The occurrence in higher plants (i.e., in the morning glory family) of ergot alkaloids that hitherto had been known only as constituents of lower fungi, contradicted the experience that certain substances are typical of and restricted to respective plant families. It is indeed a very rare exception to find a characteristic group of substances, in this case the ergot alkaloids, occurring in two divisions of the plant kingdom broadly separated in evolutionary history.

Our results were confirmed, however, when different laboratories in the United States, Germany, and Holland subsequently verified our investigations on the ololiuhqui seeds.

Nevertheless, the skepticism went so far that some persons even considered the possibility that the seeds could have been infected with alkaloid-producing fungi. That suspicion, however, was ruled out experimentally.

These studies on the active principles of ololiuhqui seeds, although they were published only in professional journals, had an unexpected sequel. We were apprised by two Dutch wholesale seed companies that their sale of seeds of Ipomoea violacea, the ornamental blue morning glory, had reached unusual proportions in recent times. They had heard that the great demand was connected with investigations of these seeds in our laboratory, about which they were eager to learn the details. It turned out that the new demand derived from hippie circles and other groups interested in hallucinogenic drugs. They believed they had found in the ololiuhqui seeds a substitute for LSD, which was becoming less and less accessible.

The morning glory seed boom, however, lasted only a comparatively short time, evidently because of the undesirable experiences that those in the drug world had with this "new" ancient inebriant. The ololiuhqui seeds, which are taken crushed with water or another mild beverage, taste very bad and are difficult for the stomach to digest. Moreover, the psychic effects of ololiuhqui, in fact, differ from those of LSD in that the euphoric and the hallucinogenic components are less pronounced, while a sensation of mental emptiness, often anxiety and depression, predominates. Furthermore, weariness and lassitude are hardly desirable effects as traits in an inebriant. These could all be reasons why the drug culture's interest in the morning glory seeds has diminished.

Only a few investigations have considered the question whether the active principles of ololiuhqui could find a useful application in medicine. In my opinion, it would be worthwhile to clarify above all whether the strong narcotic, sedative effect of certain ololiuhqui constituents, or of chemical modifications of these, is medicinally useful.

My studies in the field of hallucinogenic drugs reached a kind of logical conclusion with the investigations of ololiuhqui. They now formed a circle, one could almost say a magic circle: the starting point had been the synthesis of lysergic acid amides, among them the naturally occurring ergot alkaloid ergobasin. This led to the synthesis of lysergic acid diethylamide, LSD. The hallucinogenic properties of LSD were the reason why the hallucinogenic magic mushroom teonanacatl found its way into my laboratory. The work with teonanacatl, from which psilocybin and psilocin were isolated, proceeded to the investigation of another Mexican magic drug, ololiuhqui, in which hallucinogenic principles in the form of lysergic acid amides were again encountered, including ergobasin-with which the magic circle closed.

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