Muutama quotti:
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Entheogen Review, vol. VIII (4). Winter Solstice. 1999 (s. 136):
MORE STIPA ROBUSTA
I have ten Stipa robusta plants growing outside and I experimented with it for about a year. My conclusion is that it is does not have visionary effects. It is a tranquilizer par excellence, and has a strong sedative effect that lasts about three hours and is free of side-effects. In The Botany and Chemistry of Hallucinogens by SCHULTES and HOFMANN, lysergic acid amide (ergine) is described as a strong tranquilizer with very little psychoactivity. HOFMANN should know; he is the “father of LSD” and did extensive research on related compounds. Ergine is not useful as an entheogen, but it’s great for insomnia! Yet individuals persist in trying to use it as a visioninducing material, simply because it is structurally related to LSD. — B. GREEN
This letter and the previous one bring up an interesting point. It is assumed by some that ergine is the primary visionary component in Ipomoea violacea and Argyreia nervosa. However, this may not be the case. K. TROUT has found that some morning glories are very LSD-like, and others are not (both within commercially available “heavenly blue” strains for example). There may be something else at work here that has not been adequately examined. It appears that HOFMANN did not evaluate all of the different chemicals found in I. violacea, and at least one that he did evaluate may have been visionary at doses higher than he took; he evaluated isoergine only up to the 2 mg level, and found it to be predominantly sedative without visual effects. JONATHAN OTT has pointed out that this compound might be psychoptic at higher levels (OTT 1993). We simply do not know at this point. It is also worth noting that lysergic acid-L-2-propanolamide, or ergonovine, has been reported as having mild visionary effects (as well as producing lassitude and leg cramps) in doses of 2–10 mg (HOFMANN 1978; BIGWOOD et al. 1979), and this compound is found in both Argyreia nervosa and Ipomoea violacea (CHAO & DER MARDEROSIAN 1973, listed under MOIR & DUDLEY’S synonym ergometrine), as is elymoclavine, which OTT has stated is “evidently psychoptic” (OTT 1993). Other possible players include the N-(1-hydroxyethyl)-amides of ergine and/or isoergine. The Botany and Chemistry of Hallucinogens notes:
The psychotomimetic activity of lysergic acid amide and its marked narcotic component was ascertained from self-experiment by Hofmann (1963). This action of dlysergic acid amide was later confirmed by comparative systematic investigations by Solms (1956a). He described the action as follows: “LA-111 induces indifference, a decrease in psychomotor activity, the feeling of sinking into nothingness, and a desire to sleep…until finally an increased clouding of consciousness does produce sleep.” Heim et al. (1968) concluded from experiments in man that ololiuqui and its main constituents (lysergic acid amide, isolysergic acid amide) did not produce typical psychotomimetic symptoms but rather effects more like those encountered in toxic psychoses resulting from the action of a drug such as scopolamine. [Note: I never had effects even remotely similar to what was experienced from belladonna. — K. TROUT] Only little information is available on the activity of isolysergic acid amide (isoergine). After taking 2.0 mg orally, Hofmann experienced tiredness, apathy, a feeling of mental emptiness, and the unreality and complete meaninglessness of the outside world. (Hofmann, 1963)” (SCHULTES & HOFMANN 1973)
Ergine may not be the psychoptic agent in morning glories that are active, or if it is then it is likely not the only player involved in producing visual activity. Between 1972 and 1983, K. TROUT ate Ipomoea violacea seeds or seed-extract several dozen times with wildly varying results ranging from powerfully colorful visuals to sedative effects. The highest amount he evaluated during those years was around 2000 heavenly blue seeds, but usually about 300 seeds were used. K. TROUT also consumed Argyreia nervosa seeds about 20 times, using amounts from 10–24 seeds, (he recommends the 18– 22 range), and he reported a colorful visuals resulting each time. However, he also reported that in every instance of either seed there was at least some sedative component. It seems probable that the psychoptic effects produced by these seeds involves an interaction or synergism between two or more of the chemicals present; HOFMANN only evaluated pure alkaloids not mixtures. It is also possible that higher doses of ergine may be more likely to produce visual effects, as was the case with ergonovine (BIGWOOD et al. 1979).
BIGWOOD, J. et al. 1979. “Entheogenic Effects of Ergonovine,”
Journal of Psychedelic Drugs 11(1–2): 147–149.
CHAO, J.-M. & A.H. DER MARDEROSIAN. 1973. “Identification of
ergoline alkaloids in the genus Argyreia and related genera and their
chemotaxonomic implications in the Convolvulacea,” Phytochemistry
12: 2435–2440.
SCHULTES, R.E. & HOFMANN, A. 1973/1980. The Botany and Chemistry
of Hallucinogens. C. THOMAS.
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Alexander Shulgin. TIHKAL. Transform Press, 1997. #26. LSD-25
http://www.erowid.org/library/books_onl ... al26.shtml
LA-111, ergine, d-lysergamide. This is an active compound and has been established as a major component in morning glory seeds. It was assayed for human activity, by Albert Hofmann in self-trials back in 1947, well before this was known to be a natural compound. An i.m. administration of a 500 microgram dose led to a tired, dreamy state with an inability to maintain clear thoughts. After a short period of sleep, the effects were gone and normal baseline was recovered within five hours. Other observers have confirmed this clouding of consciousness leading to sleep. The epimer, inverted at C-8, is isoergine or d-isolysergamide, and is also a component of morning glory seeds. Hofmann tried a 2 milligram dose of this amide, and as with ergine, he experienced nothing but tiredness, apathy, and a feeling of emptiness. Both compounds are probably correctly dismissed as not being a contributor to the action of these seeds. It is important to note that ergine, as well as lysergic acid itself, is listed as a Schedule III drug in the Controlled Substances Act, as a depressant. This is, in all probability, a stratagem to control them as logical precursors to LSD.
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Ergonovine is a naturally occurring, water-soluble ergot alkaloid, found in both ergot preparations and in many species of morning glory seeds, and there are several reports of LSD-like action at oral levels of between two and ten milligrams. It has an important use in obstetrics, again as an oxytocic, at about a tenth of this dose. This pharmacological potential must be respected in psychopharmacological trials. The one-carbon homologue (the butanolamide rather than the propanolamide) is called methergine or methylergonovine. It is a synthetic ally and is orally effective as an oxytocic at a dosage of 200 micrograms. It also has an LSD-like action at ten times this level.
Although there are many other chemical treasures in the ergot fungal world, I would like to wrap this commentary up with a return to the topic of morning glory seeds. Four additional alkaloids of the ergot world must be acknowledged as being potentially participating factors in the MGS story. With each of these, the primary ergoline ring system is largely intact but the amide function is completely gone. The carboxyl group has been reduced to the alcohol to give elymoclavine. There is the related molecule present which is the isomer with the double bond moved to be conjugated with the aromatic ring; it is called lysergol. There is the same molecule but with a hydroxy group attached to the 8-position carbon atom (an ethyleneglycol!) ; it is called penniclavine. And lastly, that D-ring can actually be opened between the 5 and 6 positions, to give us a secondary amine tryptamine derivative, chanoclavine. To be completely anally retentive in this Ipomoea inventory, mention must be made of five alkaloids that are present in truly trace amounts, all of which have no oxygen atoms present whatsoever on that substitution on the ergoline 8-position. These are the 8-methyl isomers agroclavine, setoclavine, festuclavine and cycloclavine, and the methylene analogue lysergene. These structures in effect define absolute obscurity, and most probably do not contribute to the morning glory intoxication state. But the others, some present is sizable amounts, may someday help explain why the pharmacology of these seeds is so different than that of the major isolates, the ergines.
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Teonanácatl and Ololiuqui, two ancient magic drugs of Mexico
Bulletin on Narcotics. Issue 1, 1971; 3-14
by Albert Hofmann
TABLE I Alkaloids of the seeds of Ipomoea violacea L. (In percentages) [Poistin listasta Rivea corymbosan]
- d-Lysergic acid amide (ergine) * 0.035
d-Isolysergic acid amide (isoergine) *0.005
Chanoclavine * 0.005
Elymoclavine * 0.005
Lysergol * —
Ergometrine * 0.005
Total alkaloid content * 0.06
Pharmacological and Mental Effects
D-Lysergic acid amide (LA-111 = designation of the experimental drug) was tested pharmacologically during the course of investigations on d-lysergic acid diethylamide (LSD-25) and related compounds long before it was known to be a component of ololiuqui.
LA-111 elicited strong autonomic symptoms in rabbits, e.g. mydriasis, piloerection, and hyperthermia, which were accompanied by a general motor restlessness. The antiserotonin activity tested on the isolated rat uterus, has a value of 4 on a scale on which LSD-25 is 100 ([57] ).
Psychotomimetic activity of LA-111, having a marked narcotic component, could be ascertained from the first self-experiment by Hofmann ([45] ).
This action of d-lysergic acid amide was later confirmed by comparative systematic investigations by Solms ([58] , [59] ). He describes the action as follows: LA-111 induces indifference, a decrease in psychomotor activity, the feeling of sinking into nothingness and a desire to sleep... until finally an increased clouding of consciousness does produce sleep.
Only little information is available on the activityof d-isolysergic acid amide (isoergine). After taking 2.0 mg orally Hofmann experienced tiredness, apathy, a feeling of mental emptiness and of the unreality and complete meaninglessness of the outside world ([45] ).
D-Lysergic acid N-(1-hydroxyethyl) amide induces contractions in the isolated uterus of the guinea pig and in the rabbit uterus in situ, showing about 30-50% of the activity of ergometrine. In mice and rabbits it produced the syndrome of central sympathetic stimulation, such as piloerection, mydriasis, and hyperthermia, which suggests that it could have an LSD-like activity, but this hypothesis has not yet been verified by experiments on humans ([60] ).
Elymoclavine and lysergol elicit an excitation syndrome in various animals that is caused by a central stimulation of the sympathetic nerves ([61] ) which seems to indicate psychotomimetic activity. Results of clinical tests are not as yet available.
Psychotomimetic effects are unknown for ergometrine, which is used to a large extent in obstetrics as a uterotonic and hemostatic agent. In small dosages, which are administered for this purpose, the alkaloid apparently has no action on the psychic functions. Its occurrence in the alkaloid mixture of ololiuqui can thus have no significant effects on its mental action.
Furthermore, chanoclavine, which has no outstanding pharmacological activity, appears to play no part in the occurrence of the psychic effects of ololiuqui.
According to the results of experiments performed thus far with pure alkaloids, it appears that d-lysergic acid amide, d-lysergic acid N-(1-hydroxyethyl) amide, elymoclavine, and lysergol, and possibly also d-isolysergic acid amide are mainly responsible for the psychic effect of ololiuqui.
045. A. Hofmann, Botan. Museum Leaflets, Harvard Univ. 20, 194 (1963).
046. F. Arcamone, C. Bonino, E. B. Chain, A. Ferretti, P. Pennella, A. Tonolo, and L. Vero, Nature 187, 238 (1960).
047. A. Hofmann, R. Brunner, H. Kobel and A. Brack, Helv. Chim. Acta 40, 1358 (1957).
048. M. Abe, T. Yamano, Y. Kozu, and M. Kusumoto, J. Agr. Chem. Soc. Japan, 29, 364 (1955).
049. A. Stoll, A. Hofmann and W. Schlientz, Helv. Chim. Acta 32, 1947 (1949).
050. A. Stoll and A. Hofmann, Helv. Chim. Acta 26, 944 (1943).
057. A. Cerletti, E. Schlager, F. Spitzer and M. Taeschler, Schweiz. Apoth. Ztg. 101, 210 (1963).
058. H. Solms, J. Clin. Exptl. Psychopath. Quart. Rev. Psychiat. Neurol., 17, 429 (1956).
059. H. Solms, Praxis 45, 746 (1956).
060. A. Glässer, Nature 189, 313 (1961).
061. T. Yui and Y. Takeo, Japan J. Pharmacol. 7, 157 (1958).
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