Ergine, also known as lysergic acid amide (LSA or LAA) as well as LA-111, is a psychoactive compound of the ergoline and lysergamide families related to lysergic acid diethylamide (LSD).[10][13][9][14] It is an alkaloid and is found in certain plants such as morning glory seeds and in certain fungi such as Claviceps purpurea (ergot) and Periglandula species.[13] The latter fungi have a symbiotic relationship with morning glories and are the source of the ergine in their seeds.[13] Ergine is orally active and produces relatively mild hallucinogenic effects as well as pronounced sedative effects.[10][15][16][17][18][19][20]

The most common sources of ergine for use as a drug are the seeds of morning glory species including Ipomoea tricolor (tlitliltzin), Ipomoea corymbosa (ololiuhqui), and Argyreia nervosa (Hawaiian baby woodrose).[13][21][15][22] Morning glory seeds have a history of entheogenic use in Mesoamerica dating back at least hundreds of years.[13][17][23] They have also since been used by many Westerners.[24] In addition to ergine, morning glory seeds contain other ergolines such as lysergic acid hydroxyethylamide (LSH), lysergic acid propanolamide (ergonovine), and isoergine.[16][17][13] Some of these compounds are pharmacologically active and are thought to contribute to the effects of the seeds as well.[16][17][13][25][26] There has been debate about the role of ergine in causing the psychedelic effects of morning glory seeds.[15][27][28][19]

Ergine was first described by Sidney Smith and Geoffrey Timmis after they isolated it from ergot in 1932.[12] It was first synthesized subsequent to its isolation in the 1930s.[16][29] Albert Hofmann, the discoverer of LSD's psychedelic effects in 1943, evaluated the effects of ergine in humans in 1947 and desccribed the results many years later.[15][16][26][30] He and his colleagues also isolated ergine from morning glory seeds in 1960.[31][32][16][13] Morning glory seeds started to become frequently used as a recreational drug that same year[24] and has been widely used since.[13][31][33][34] Recreational use of morning glory seeds may be increasing due to their inexpensiveness, widespread availability, and lack of legal restrictions.[10][31] Ergine has been encountered as a novel designer drug in Europe.[35] Ergine, though not morning glory seeds, has become a controlled substance in various places in the world.[36][37]

Use

Ergine is most commonly used as a drug in the form of morning glory seeds, including those of Ipomoea tricolor (tlitliltzin), Ipomoea corymbosa (ololiuhqui), and Argyreia nervosa (Hawaiian baby woodrose).[13] They may be consumed whole and intact, crushed or ground up, or drunk as an extract following soaking of the seeds in water.[38][9][10] A hallucinogenic dose (~0.5–1 mg) is 150 to 200 seeds (3–6 g) of Ipomoea tricolor (0.02% ergine by dry weight) or 5 to 10 seeds (0.5–1 g) of Argyreia nervosa (0.14% ergine by dry weight).[38][9][10][24][19] The onset is 0.3 to 3 hours and the duration is 4 to 10 hours.[38][9][10]

Ergine may be used as a drug in pure or purified form as well, either isolated or synthesized.[15][18][39] Albert Hofmann and colleagues found that a 0.5 to 1 mg dose by intramuscular or subcutaneous injection produced relatively weak hallucinogenic effects and marked sedation.[15][16][30][24][18][39] Another study described the effects of pure ergine by injection but the doses were not clearly provided (although appeared to be around 0.1–1 mg).[24][31][40][41] Based on the preceding studies, Alexander Shulgin describes pure ergine as having a dosage of 0.5 to 1 mg and being 10-fold less potent than LSD, but as being "not hallucinogenic".[27] Hofmann also stated that ergine was 10- to 20-fold less potent than LSD and that it had qualitatively different effects.[30] Robert Oberlender has stated that ergine is about 30-fold less potent than LSD in humans.[42] Heim and colleagues assessed ergine at very high doses of 3 to 6 mg orally and observed toxic-like effects, whereas isoergine at 2 to 5 mg orally produced notable hallucinogenic effects, including some euphoria, synaesthesia, and altered time perception.[19][43][26]

Sleepy grass (Achnatherum robustum) and Claviceps paspali (ergot) have similar ergoline constituents as morning glory seeds and have also been used to produce psychoactive effects, albeit rarely.[44][45]

Effects

Subjective effects

Ergine has only been given a minuscule amount of attention. Albert Hofmann and his colleagues self-administered ergine.[16] In addition, it was assessed in two clinical studies by other researchers.[40][26] Synthetic ergine was used in all of these cases.[40][16][26] Hofmann stated that ergine induces a "psychotomimetic" effect with "a marked narcotic component": "Tired, dreamy, incapable of clear thoughts. Very sensitive to noises which give an unpleasant sensation."[16] There are parallels between Hofmann's comments and the ones in the two trials:[16]

Clinical studies of ergine's effects
Hofmann 1963[16] Heim 1968[26] Solms 1956[40][41]
"dysphoria" "irritative depressive moods"
"incapable of clear thoughts" "impairment of concentration"

"clouding of consciousness"

"impaired concentration"

"clouding of consciousness"

"With middle to strong doses in 1 subject work became increasingly difficult after 30 minutes"

"Desire to lie down and sleep. Genuine physical and mental tiredness, which is not experienced as an unpleasant sensation. Slept for 3 hours." "test subject SB [...] had to go to bed after an antineoplastic injection and did not recover until the following day."

"In the fourth and fifth study periods, however, they appeared to be sufferingly exhausted and even sleepy and dazed." [isoergine]

"and an immediate desire to sleep, after which he slept for three hours during the day".
"a feeling of mental emptiness and of the unreality and complete meaninglessness of the outside world". [isoergine] "In the test subject PS (5 mg), severe nausea with a drop in blood pressure suddenly occurred after 3½ hours, which was controlled with analeptics and antinausea after about 30 minutes. At the same time, the test subject experienced a feeling of total annihilation and fear of death, which subsided after vomiting about 60 minutes later, but only completely subsided during the course of the night." [isoergine]

"In the fourth and fifth study cross-sections, they complained of difficulty in thinking and a lack of ideas." [isoergine]

"Indifference"

"a feeling of sinking into nothing"

Heim 1968 also noted "paraesthesia", "synesthesia" and an "overestimation of the time that had passed" (isoergine), but also concluded, "our experiments with ᴅ-lysergic acid amide also confirm the results that Sᴏʟᴍꜱ had made with this substance, namely a predominantly sedative intoxication." Hofmann emphasized this sedative effect:[excessive quote]

"Furthermore there is not only a quantitative difference between the principles of Ipomoea [tricolor] and Turbina corymbosa and LSD; there is likewise a qualitative one, LSD being a very specific hallucinogen, whereas the psychic effects of lysergic acid amide and the total alkaloids of these two plants are characterized by a pronounced narcotic component (Hofmann, 1968)."[46]

"A substance very closely related to LSD, the monoethylamide of lysergic acid (LAE-32), in which an ethyl group is replaced by a hydrogen atom on the diethylamide residue of LSD, proved to be some ten times less psychoactive than LSD. The hallucinogenic effect is also qualitatively different: it is characterized by a narcotic component. This narcotic effect is yet more pronounced in lysergic acid amide (LA-111), in which both ethyl groups of LSD are displaced by hydrogen atoms. These effects, which I established in comparative self-experiments with LA-111 and LAE-32, were corroborated by subsequent clinical investigations."[30]

"The experience had some strong narcotic effect, but at the same time there was a very strange sense of voidness. In this [void], everything loses its meaning. It is a very mystical experience."[14]

Physiological effects

While its physiological effects vary from person to person, the following symptoms have been attributed to the consumption of ergine or ergine containing seeds: sedation, visual hallucinations, auditory hallucinations, euphoria, loss of motor control, nausea, vasoconstriction, delusions, anxiety, paranoia, and irregular heartbeats.[22][47][48][49]

One study found that two of four human subjects experienced cardiovascular dysregulation and the study had to be halted, concluding that the ingestion of seeds containing ergine was less safe than commonly believed. Importantly this may have been a product of other substances within the seeds. The same study also observed that reactions were highly differing in type and intensity between different subjects.[49]

Side effects

A 2016 study showed that penniclavine was the predominant alkaloid in Ipomoea tricolor seeds.[50] Ergoclavines are known to cause convulsive ergotism,[51] the milder form of ergotism. Gangrenous ergotism is caused by ergopeptines: the complex peptide moiety forces persistence at the receptor sites.[52] Ergopeptines are rare in Convolvulaceae, being found in 10 species,[52][53] not including the three that are commonly ingested, although Paulke 2014 says analytical evidence suggests that A. nervosa contains ergopeptines.[54] Many people desire purified seed extracts, but the efficacy of this is questionable, as even pure ergine and ergonovine have shown toxic effects.

The side effects of ergine have been described as follows: "The expression and behavior of the test subjects changed just 45 minutes after taking the substance: the test subjects appeared to be suffering, their facial expressions were deteriorating as if they had suffered a serious illness, and their movements were noticeably slower. [...] In the self-reports of both test subjects, complaints about vegetative symptoms predominated: unpleasant, flu-like feeling of illness, nausea, sudden onset of nausea, with vomiting that could be stopped with 2 cm3 of Cyclicinum hydrochloricum. In addition, sensations of heat, sweating, dizziness, a feeling of heaviness and general tiredness were observed."[26]

And the side effects of ergonovine have been described as follows: "Walking in this dreamy state was difficult due to leg cramps and slight incoordination. There was always a great desire to lie supine. [...] One of us (J.B.) felt the cramping in the legs as painful and debilitating. [...] We all had a slight hangover the following morning. [...] The mild entheogenic effects of ergonovine are similar to those of LSD. However, in dramatic contrast to LSD, the somatic effects of ergonovine greatly overshadow its psychic effects, so much so that we had no wish to ingest more than 10.0 mg, [...]".[55]

Like other psychedelics, ergine is not considered to be addictive. Additionally, there are no known deaths directly associated with pharmacological effects of ergine consumption. All associated deaths are due to indirect causes, such as self-harm, impaired judgement, and adverse drug interactions. One known case involved a suicide that was reported in 1964 after ingestion of morning glory seeds.[56] Another instance is a death due to falling off of a building after ingestion of Hawaiian baby woodrose seeds and alcohol.[57] A study gave mice 3000 mg/kg with no lethal effects.[citation needed]

Chemical coatings on seeds

Garden seeds, in general, may be coated with fungicides et. al. (e.g. neonicotinoids, Thiram, and ApronMaxx). It is rumored that this is the cause of the severe adverse effects that have been observed, but the seeds, themselves, contain toxins, specifically glycoresins[58][59] and ergoclavines.[51] Some[who?] even believe that an emetic chemical is purposely added to the seeds to prevent people from ingesting them, but that has never been proven.[citation needed] One 1964 article states that reported adverse effects must come from the seeds, as the stated insecticide is too "inocuous" to humans to be responsible.[48][56][60]

A related rumor is that the seeds contain cyanogenic glycosides. The UseNet post on which this is based contains two references, but neither of them support that claim,[61] and Eckart Eich says that they probably don't occur in many Convolvulaceae.[52] There is a similar claim in a publication from 1973, warning about "a strychnine-like alkaloid",[62] but that is probably just a misapplication of the claim that peyote contains strychnine, which, itself, is a rumor.[63]

Overdose

Cases of overdose of ergine and morning glory seeds and associated toxicity have been reported.[19]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

The interactions of ergine and of morning glory seeds have been discussed.[19]

Pharmacology

Pharmacodynamics

LSA and LSD activities
Receptor Affinity (Ki, nM) Ratio
LSA LSD
5-HT1A 73 1.6 46:1
5-HT2A 28–132 (Ki)
1.1–58 (EC50Tooltip half-maximal effective concentration)
47–82% (EmaxTooltip maximal efficacy)		 0.87–1.1 (Ki)
0.52–3.6 (EC50)
60–86% (Emax)		 32–120:1
2–16:1
0.78–0.95:1
5-HT2B 54–115 (EC50)
40–55% (Emax)		 0.68–34 (EC50)
62–73% (Emax)		 3–79:1
0.65–0.75:1
5-HT2C 798 7.8 102:1
D1 (pig) 832 87 10:1
D2L 891 155 6:1
D2S 145 25 6:1
D3 437 65 7:1
D4.4 141 30 5:1
α1 912 60 15:1
α2 62 1.0 62:1
Notes: All proteins are human unless otherwise specified. Sources: [64][65][66]

Ergine interacts with serotonin, dopamine, and adrenergic receptors similarly to but with lower affinity than lysergic acid diethylamide (LSD).[64][65] It is known to act as an agonist of the serotonin 5-HT2A and 5-HT2B receptors similarly to LSD, albeit much less potently and with reduced activational efficacy.[65] The drug has about 4.3% of the antiserotonergic activity of LSD in the isolated rat uterus in vitro.[42][67] The psychedelic effects of ergine can be attributed to activation of serotonin 5-HT2A receptors.[68][69][70]

Chemistry

See also: Lysergamides

Ergine, also known as lysergic acid amide (LSA) or as lysergamide, is a ergoline and lysergamide. It is the simplest lysergamide and is the parent structure of this family of compounds. Hence, all lysergamides are derivatives of ergine. Lysergic acid diethylamide (LSD) is the analogue of ergine with two ethyl groups substituted on its amide moiety.

The extraction of ergine from morning glory seeds has been described.[71][72]

Natural occurrence

Ergine is not a biosynthetic endpoint itself, but rather a hydrolysis product of lysergic acid hydroxyethylamide (LSH), lysergic acid propanolamide (ergonovine), and ergopeptines or their ergopeptam precursors.[73][74][75][76][77]

LSH is very vulnerable to this hydrolysis,[24][46] and many analyses of ergoline-containing fungi show little to no LSH and substantial amounts of ergine.

An ergine analog, 8-hydroxyergine, has also been found in natural products in two studies.[78][79] Methylergonovine and methysergide (1-methylmethylergonovine) have also been found in a natural product in one study;[54] these are documented as semisynthetic compounds, so the findings need to be repeated for certainty. The aforementioned chemicals are the only natural lysergamides.

LSH and ergine are predominant in Claviceps paspali,[80][81][82] but are only found in trace amounts in the more well-known Claviceps purpurea.[83][84] Both are ergot-spreading fungi. The major products of C. purpurea are ergopeptines, but C. paspali does not generate ergopeptines.[77] Ergonovine is the only lysergamide in C. purpurea in a substantial amount.[84]

LSH and ergine are also found in the related fungi, Periglandula, which are permanently connected with Ipomoea tricolor, Ipomoea corymbosa, Argyreia nervosa ("morning glory", coaxihuitl, Hawaiian baby woodrose), and an estimated over 440 other Convolvulaceae[85] (ergolines have been identified in 42 of these plants and not all of them contain ergine).[52] Ergonovine is present in Ipomoea tricolor in one-tenth to one-third of the amount of ergine.[50] This variable may account for the varying reports about the psychedelic effect of these seeds.[25]

Other fungi that have been found to contain LSH and/or ergine:

  • Unidentified Acremonium species that infects sleepy grass (C. purpurea also infects sleepy grass[86]).[79]
  • Unidentified Acremonium species that infects drunken horse grass[87]
  • Acremonium coenophialum (infects Festuca arundinacea)[88]
  • Epichloë gansuensis var. inebriens (infects drunken horse grass)[89]
  • Metarhizium brunneum[90]
  • Metarhizium acridum[90]
  • Metarhizium anisopliae[90]
  • Metarhizium flavoviride[90]
  • Metarhizium robertsii[90]
  • Aspergillus leporis[91]
  • Aspergillus homomorphus[91]
  • Aspergillus hancockii[91]

All of these fungi are related to Claviceps fungi. Aspergillus is considered to be a more distant relative of Claviceps.

Other fungi that possibly contain ergine (i.e. they have been found to contain ergonovine and/or ergopeptines):

  • Claviceps hirtella[92]
  • Neotyphodium lolii[93]
  • Unidentified Epichlöe and Neotyphodium (asexual forms of Epichlöe) species[94]
  • Aspergillus fumigata[95]
  • Aspergillus flavus[95]
  • Botritis fabae[95]
  • Curvularia lunata[95]
  • Geotrichum candidum[95]
  • Balansia cyperi[95]
  • Balansia claviceps[95]
  • Balansia epichloë[95]
  • Epichloë amarillans[96]
  • Epichloë cabralii (H)[97]
  • Epichloë canadensis (H)[98][99]
  • Epichloë coenophiala (H)[98][100][101][102]
  • Epichloë festucae[96]
  • Epichloë festucae var. lolii[93][103]
  • Epichloë festucae var. lolii x E. typhina (H)[98][104]
  • Epichloë inebriens[96]
  • Epichloë glyceriae[96]
  • Epichloë mollis[98]
  • Epichloë typhina[95]
  • Epichloë typhina ssp. poae[96][97]
  • Epichloë typhina ssp. clarkii[105]
  • Epichloë sp. AroTG-2(H)[106]
  • Epichloë sp. FaTG-2(H)[98][100][102][107][104]
  • Epichloë sp. FaTG-4(H)[98][102]
  • Hypomyces aurantius[95]
  • Sepedonium sp.[95]
  • Cunnigbamella blakesleana[95]
  • Mucor biemalis[95]
  • Rhizopus nigricans[95]

Biosynthesis

Biosynthesis of the ergoline scaffold
Biosynthesis of the ergoline scaffold

The biosynthetic pathway to ergine starts like most other ergoline alkaloid- with the formation of the ergoline scaffold. This synthesis starts with the prenylation of L-tryptophan in an SN1 fashion with dimethylallyl diphosphate (DMAPP) as the prenyl donor and catalyzed by prenyltransferase 4-dimethylallyltryptophan synthase (DMATS), to form 4-L-dimethylallyltryptophan (4-L-DMAT). The DMAPP is derived from mevalonic acid. A three strep mechanism is proposed to form 4-L-DMAT: the formation of an allylic carbocation, a nucleophilic attack of the indole nucleus to the cation, followed by deprotonation to restore aromaticity and to generate 4-L-DMAT.[108] 4-Dimethylallyltyptophan N-methyltransferase (EasF) catalyzes the N-methylation of 4-L-DMAT at the amino of the tryptophan backbone, using S-Adenosyl methionine (SAM) as the methyl source, to form 4-dimethylallyl-L-abrine (4-DMA-L-abrine).[108] The conversion of 4-DMA-L-abrine to chanoclavine-I is thought to occur through a decarboxylation and two oxidation steps, catalyzed by the FAD dependent oxidoreductase, EasE, and the catalase, EasC. The chanoclavine intermediate is then oxidized to chanoclavine-l-aldehyde, catalyzed by the short-chain dehydrogenase/reductase (SDR), EasD.[108][109]

Formation of argoclavine
Formation of argoclavine

From here, the biosynthesis diverges and the products formed are plant and fungus-specific. The biosynthesis of ergine in Claviceps purpurea will be exemplified, in which agroclavine is produced following the formation of chanoclavine-l-aldehyde, catalyzed by EasA through a keto-enol tautomerization to facilitate rotation about the C-C bond, followed by tautomerization back to the aldehyde and condensation with the proximal secondary amine to form an iminium species, which is subsequently reduced to the tertiary amine and yielding argoclavine.[108][109] Cytochrome P450 monooxygenases (CYP450) are then thought to catalyze the formation of elymoclavine from argoclavine via a 2 electron oxidation. This is further converted to paspalic acid via a 4 electron oxidation, catalyzed by cloA, a CYP450 monooxygenase. Paspalic acid then undergoes isomerization of the C-C double bond in conjugation with the acid to form D-lysergic acid.[108] While the specifics of the formation of ergine from D-lysergic acid are not known, it is proposed to occur through a nonribosomal peptide synthase (NRPS) with two enzymes primarily involve: D-lysergyl peptide synthase (LPS) 1 and 2.[108][109]

History

Ergine was first obtained by Sidney Smith and Geoffrey Willward Timmis in 1932.[12]

Albert Hofmann was first to identify ergine as a natural constituent of Turbina corymbosa seeds.[22]

Albert Hofmann describes ergine as "the main constituent of ololiuhqui".[110] Ololiuhqui was used by South American healers in shamanic healing ceremonies.[47] Similarly, ingestion of morning glory seeds by Mazatec tribes to "commune with their gods" was reported by Richard Schultes in 1941 and is still practiced today.[111][47]

According to the ethnobotanist R. Gordon Wasson, Thomas MacDougall and Francisco Ortega ("Chico"), a Zapotec guide and trader, should be credited for the discovery of the ceremonial use of Ipomoea tricolor seeds in Zapotec towns and villages in the uplands of southern Oaxaca. The seeds of both Ipomoea tricolor and Rivea corymbosa, another species which has a similar chemical profile, are used in some Zapotec towns.[112]

The Central Intelligence Agency conducted research on the psychedelic properties of Rivea corymbosa seeds for MKULTRA.[113]

My chemical investigations of Ololiuhqui seeds led to the unexpected discovery that the entheogenic principles of Ololiuhqui are alkaloids, especially lysergic acid amide, which exhibits a very close relationship to lysergic acid diethylamide (=ʟsᴅ). It follows therefrom that ʟsᴅ, which hitherto had been considered to be a synthetic product of the laboratory, actually belongs to the group of sacred Mexican drugs.

— Albert Hofmann, Burg i.L., Switzerland, November 1992[114]

Society and culture

The legality of consuming, cultivating, and possessing ergine varies depending on the country.

Australia

In most Australian states, the consumption of ergine containing materials is prohibited under state legislation.

Canada

In Canada, ergine is not illegal to possess as it is not listed under Canada's Controlled Drugs and Substances Act, though it is likely illegal to sell for human consumption.[36]

New Zealand

In New Zealand, ergine is a controlled drug, however the plants and seeds of the morning glory species are legal to possess, cultivate, buy, and distribute.

United Kingdom

Ergine is considered a Class A substance in the United Kingdom, categorized as a precursor to LSD.

United States

There are no laws against possession of ergine-containing seeds in the United States. However, possession of the pure compound without a prescription or a DEA license would be prosecuted, as ergine, under the name "lysergic acid amide", is listed under Schedule III of the Controlled Substances Act.[37]

See also

References

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  2. ^ Genest K, Sahasrabudhe MR (1966). "Alkaloids and Lipids of Ipomoea, Rivea and Convolvulus and Their Application to Chemotaxonomy". Economic Botany. 20 (4): 416–428. doi:10.1007/BF02904064. ISSN 0013-0001. JSTOR 4252802.
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  7. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União. Archived from the original on 2023-08-27. Retrieved 2023-08-27.
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  9. ^ a b c d e f Tittarelli R, Mannocchi G, Pantano F, Romolo FS (January 2015). "Recreational use, analysis and toxicity of tryptamines". Curr Neuropharmacol. 13 (1): 26–46. doi:10.2174/1570159X13666141210222409. PMID 26074742. Ergine, or lysergic acid amide (LSA), is an alkaloid of the ergoline family closely related to LSD, found in the seeds of Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea (Morning Glories). Hallucinogenic activity of LSA occurs with 4-10 seeds of Argyreia nervosa or with 150–200 seeds (3–6 g) of Ipomoea violacea: seeds could be crushed or eaten whole, or also drunk as an extract, after soaking in water [42]. The onset of the hallucinatory effects, after ingestion of Hawaiian Baby Woodrose, is from 20 to 40 minutes and their total duration is from 5 to 8 hours: the plateau is reached after 4-6 hours and the return to normality is after 1-2 hours from the plateau. [...] However, as regards to the assumption of the Morning Glory seeds, the onset of the hallucinatory effects is from 30 to 180 minutes and they last for 4 to 10 hours. The users reported that they return to normality after about 24 hours [67].
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  13. ^ a b c d e f g h i j Steiner U, Leistner E (July 2018). "Ergot Alkaloids and their Hallucinogenic Potential in Morning Glories" (PDF). Planta Med. 84 (11): 751–758. doi:10.1055/a-0577-8049. PMID 29499587.
  14. ^ a b Grof S, Hofmann A (Fall 2001) [1984]. "Stanislav Grof Interviews Dr. Albert Hofmann". MAPS Bulletin. 9 (2): 22–35.
  15. ^ a b c d e f Shulgin A. "#26. LSD-25". TiHKAL. Erowid.org. Retrieved 2012-02-03. 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.
  16. ^ a b c d e f g h i j k l Hofmann A (1963). "The Active Principles of the Seeds of Rivea Corymbosa and Ipomoea Violacea". Botanical Museum Leaflets, Harvard University. 20 (6). Harvard University Herbaria: 194–212. ISSN 0006-8098. JSTOR 41762231. Archived from the original on 28 March 2025.
  17. ^ a b c d Hofmann A (January–March 1971). "Teonanácatl and Ololiuqui, two ancient magic drugs of Mexico". Bulletin on Narcotics. 23 (1): 3–14. Archived from the original on 28 March 2025.
  18. ^ a b c Heacock RA (1975). "Psychotomimetics of the Convolvulaceae". Prog Med Chem. 11: 91–118. doi:10.1016/s0079-6468(08)70209-1. PMID 1078534. Hofmann had previously described the action of synthetic ergine (1) as being primarily of a sedative nature [33]. A subcutaneous injection of 0.5-1.0 mg of (1) has been reported to produce a powerful hypnotic action, but a relatively weak psychedelic action [52]. [...] 33. A. Hofmann, Bot. Museum Leafl. Harvard Univ., 20 (1963) 194. [...] 52. J. Soleil and L. Lalloz, Prod. Probl. Pharm., 26 (1971) 682.
  19. ^ a b c d e f Chen W, De Wit-Bos L (2020). Risk assessment of Argyreia nervosa (PDF) (Report). doi:10.21945/rivm-2019-0210. (Food supplements with) A. nervosa can be bought on internet as seeds or capsules; an average dose of A. nervosa can vary between 2 to 10 seeds (0.2–1 g) or 1 to 2 capsules (containing 75–300 mg seeds). Based on the assumptions that 1 gram seeds contains between 1.7–16 mg LSA + iso-LSA, this roughly results in an exposure to LSA + isoLSA in the range of 0.35-16 mg (seeds) or 0.13–4.8 mg (capsules). Taken together, this corresponds to 1.9–230 µg/kg bw for an individual weighing 70 kg. [...] Human volunteer studies [...] Heim, Heimann & Lukács (1968) conducted experiments with increasing doses of LSA (0.04 or 0.09 mg/kg bw [3–6 mg total]), iso-LSA (0.03, 0.06 or 0.07 mg/kg bw [2–5 mg total]), or total alkaloids from the drug Ololiuqui (Rivea corymbosa; 0.02, 0.06, 0.08 or 0.10 mg/kg bw) in healthy volunteers. [...] Ingestion of LSA led to nausea, vomiting, an illness-like state with general fatigue, sweating and dizziness, vision problems, slower movements and speech (a state of lethargy and apathy), beginning approximately 45 minutes after ingestion and becoming more pronounced over the next hours. [...] Based on these results, the authors suggest that the vegetative symptoms are probably caused by LSA while iso-LSA leads to impairment of the thinking ability and effects on a persons' conscious (Heim, Heimann & Lukács, 1968). [...] Heim, E., Heimann, H., & Lukács, G., Die psychische Wirkung der mexikanischen Droge „Ololiuqui" am Menschen. Psychopharmacologia, 1968. 13(1): p. 35-48. doi:10.1007/BF00401617
  20. ^ Moukaddam N, Ruiz P (2013). "Substance Use Disorders". International Handbook of Psychiatry. World Scientific. p. 260–290. doi:10.1142/9789814405614_0011. ISBN 978-981-4405-60-7. Hawaiian baby woodrose (Argyreia nervosa) seeds contain d-lysergic acid amide (LSA, also known as d-lysergamide), which is a substance closely related to LSD. LSA can produce mild hallucinogenic effects and is considered a controlled substance in Ireland and the United Kingdom.
  21. ^ Perrine DM (2000). "Mixing the Kykeon" (PDF). ELEUSIS: Journal of Psychoactive Plants and Compounds. New Series 4: 9. Archived from the original (PDF) on 2019-07-20. Retrieved 2008-05-05.
  22. ^ a b c Hofmann A (2009). LSD My Problem Child: Reflections on Sacred Drugs, Mysticism, and Science (4th ed.). MAPS.org. ISBN 978-0979862229.
  23. ^ Schultes RE (January 1969). "Hallucinogens of plant origin". Science. 163 (3864): 245–254. doi:10.1126/science.163.3864.245. PMID 4883616.
  24. ^ a b c d e f Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. Vol. 4. Academic Press. p. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN 978-0-12-290559-9. These compounds, although well documented as components in the Convolvulaceae, are possibly lost in several of the analyses of alkaloid composition. They are extremely unstable, and are very readily degraded into acetaldehyde and the corresponding amide, ergine or isoergine. [...] The human pharmacology of ergine, interestingly, predates its discovery as a major component in the Convolvulaceae. Following the discovery of the high potency of LSD, a large number of analogs were prepared at the Sandoz Laboratories, and many of these assayed in limited clinical experiments. Hofmann (1963a) has described the psychopharmacology of both ergine and isoergine. Following an i.m. 500-μg dose of ergine there was nausea, followed by a narcotic-like physical and mental fatigue with a high sensitivity to noises. These effects developed in about an hour, and were followed by a period of sleep; in 5 hours there was complete return to the normal state. A similar sedative-hypnotic course of activity was reported by Solms (1956a,b) in which his subjects displayed a decrease of psychomotor activity, a feeling of sinking into nothingness, a desire to sleep, followed by sleep itself. [...] It appears that the agents that are responsible for the human activity of these plants are ergine and isoergine, and possibly the corresponding α-hydroxyethylamides of lysergic acid which could serve as metabolic precursors. [...] It was in the summer of 1963 that the biological potential of morning glory seeds became widely broadcast throughout a very drug-conscious youth group, and within weeks every major news vehicle gave this "new problem" wide coverage. There were a number of notes in medical journals in the following months concerning toxicity cases, but in general, the fad quickly died out.
  25. ^ a b Ripinsky-Naxon M (1993). The Nature of Shamanism: Substance and Function of a Religious Metaphor. Albany, NY: State University of New York Press. p. 146. ISBN 9781438417417.
  26. ^ a b c d e f g Heim E, Heimann H, Lukács G (1968). "Die psychische Wirkung der mexikanischen Droge "Ololiuqui" am Menschen" [Psychotomimetic effects of the mexican drug “Ololiuqui”]. Psychopharmacologia (in German). 13 (1): 35–48. doi:10.1007/BF00401617. ISSN 0033-3158.
  27. ^ a b Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Retrieved 1 February 2025. Table 3.23 Amide analogues and pyrrole derivatives of LSD [...] Code: LA-111. Potency (mg): 0.5–1. Potency (x-LSD): 0.1a. [...] a sedative action or autonomic changes in humans; not hallucinogenic
  28. ^ "More Stipa Robusta". Entheogen Review. 8 (4): 136–. Winter 1999. Archived from the original on 28 March 2025. 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 vision-inducing 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: [...] 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. [...]
  29. ^ Stoll A, Hofmann A (1955). "Amide der stereoisomeren Lysergsäuren und Dihydro‐lysergsäuren. 38. Mitteilung über Mutterkornalkaloide" [Amides of the stereoisomeric lysergic acids and dihydrolysergic acids. 38. Report on ergot alkaloids]. Helvetica Chimica Acta. 38 (2): 421–433. doi:10.1002/hlca.19550380207. ISSN 0018-019X.
  30. ^ a b c d Hofmann A (1980). LSD, My Problem Child (PDF). New York: McGraw-Hill. ISBN 978-0-07-029325-0. A substance very closely related to LSD, the monoethylamide of lysergic acid (LAE23), in which an ethyl group is replaced by a hydrogen atom on the diethylamide residue of LSD, proved to be some ten times less psychoactive than LSD. The hallucinogenic effect of this substance is also qualitatively different: it is characterized by a narcotic component. This narcotic effect is yet more pronounced in lysergic acid amide (LA-111), in which both ethyl groups of LSD are displaced by hydrogen atoms. These effects, which I established in comparative self-experiments with LA-111 and LAE-32, were corroborated by subsequent clinical investigations. [...] 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.
  31. ^ a b c d Abram Hoffer, Humphry Osmond (1967). "Chapter II A d-Lysergic Acid Diethylamide". The Hallucinogens. Academic Press. pp. 83–236. ISBN 9780123518507. OCLC 332437. OL 26708656M. The psychological properties of lysergic acid amide (LA) were compared to LSD and to lysergic acid monoethylamide (LAE) by Solms (1956). About 0.1-1.0 mg of LA given to male subjects, chiefly physicians and chemists, were required to produce a typical LA response. This dose was similar to the dose of LAE required. But LA produced more indifference, a decrease in motor activity and more sleepiness than LAE. The subjects fell asleep after 1 hour and if not aroused they slept about 2 hours. Higher doses caused autonomic changes, emesis, diarrhea and dizziness but no hallucinations. Subjects were sometimes irritable and depressed. Thus, when the methyl groups were removed and LA produced instead of LSD, the alkaloid had much less hallucinogenic and psychomotor activity and more sedative activity. [...] R. corymbosa is only one of a large number of morning glory varieties. After it was shown that LA and other ergot alkaloids were present, it became apparent to many investigators and to many more curious nonprofessionals that morning glory plants native to North America might also be active. Before long many varieties were sampled and it became generally known that certain varieties aptly named "Heavenly Blue," "Pearly Gates" and "Wedding Bells" were especially active psychologically. According to Cohen (1963) these discoveries initiated a wave of purchases of seeds from feed and seed stores. Federal agents seized many pounds of seeds in single raids. Psychotherapists who had used LSD for psychotherapy turned to the morning glory seeds when cut off from their normal sources. Stories appeared in the daily press and before long it became widely known how to obtain LSD-like experiences cheaply without having to get LSD.
  32. ^ Hofmann A, Tscherter H (1960). "Isolierung von Lysergsäure-Alkaloiden aus der mexikanischen Zauberdroge Ololiuqui (Rivea corymbosa (L.) Hall. f.)" [Isolation of lysergic acid alkaloids from the Mexican magic drug Ololiuqui (Rivea corymbosa (L.) Hall. f.)] (PDF). Experientia (in German). 16 (9): 414–414. doi:10.1007/BF02178840. ISSN 0014-4754. Retrieved 28 March 2025.
  33. ^ Juszczak GR, Swiergiel AH (2013-01-01). "Recreational use of D-lysergamide from the seeds of Argyreia nervosa, Ipomoea tricolor, Ipomoea violacea, and Ipomoea purpurea in Poland". Journal of Psychoactive Drugs. 45 (1): 79–93. doi:10.1080/02791072.2013.763570. PMID 23662334. S2CID 22086799.
  34. ^ Burillo-Putze G, López Briz E, Climent Díaz B, Munné Mas P, Nogue Xarau S, Pinillos MA, et al. (2013-09-01). "Drogas emergentes (III): plantas y hongos alucinógenos" [Emergent drugs (III): hallucinogenic plants and mushrooms]. Anales del Sistema Sanitario de Navarra. 36 (3): 505–518. doi:10.4321/s1137-66272013000300015. PMID 24406363.
  35. ^ "EMCDDA–Europol 2008 Annual Report on the implementation of Council Decision 2005/387/JHA" (PDF). Europol. 2008. Retrieved 28 March 2025. 9. LSA ((8β)-9,10-didehydro-6-methyl-ergoline-8-carboxamide) – 29 October 2008 – Bulgaria
  36. ^ a b "Erowid LSA Vault : Legal Status". erowid.org. Retrieved 2020-05-05.
  37. ^ a b "Initial schedules of controlled substances (Schedule III), Section 812". www.deadiversion.usdoj.gov. Archived from the original on 2021-11-04. Retrieved 2020-01-17.
  38. ^ a b c Halpern JH (May 2004). "Hallucinogens and dissociative agents naturally growing in the United States" (PDF). Pharmacol Ther. 102 (2): 131–138. doi:10.1016/j.pharmthera.2004.03.003. PMID 15163594. 7. Lysergic acid amide –containing plants LSD is the best-known synthetic hallucinogen and is psychoactive at the microgram level. Although LSD does not occur in nature, a close analogue, lysergic acid amide (LSA, ergine) is found in the seeds of Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea (morning glory). Hallucinogenic activity of LSA occurs with 2–5 mg, which provides a 4- to 8-hr intoxication that reportedly has quantitative as well as qualitative differences from LSD (Schultes & Hofmann, 1980). Seeds are crushed, germinated, eaten whole, or an extract is drunk after the seeds are soaked in water. Five to 10 seeds of Argyreia nervosa or 150–200 seeds (3–6 g) of Ipomoea violacea yield average doses of LSA (Al Assmar, 1999; Borsutzky et al., 2002). The LSA content of Argyreia nervosa is 0.14% by dry weight of seeds (Chao & Der Marderosian, 1973) and is 0.02% by dry weight in Ipomoea violacea seeds (Miller, 1970).
  39. ^ a b Soleil J, Lalloz L. "Les Psychodysleptiques" [Psychodysleptics]. Produits et Problèmes Pharmaceutiques [Prod. Probl. Pharm.] (in French). 26 (11): 682–695, 757–767.
  40. ^ a b c d Solms H (1956). "Relationships between chemical structure and psychoses with the use of psychotoxic substances; comparative pharmacopsychiatric analysis: a new research method". Journal of Clinical and Experimental Psychopathology. 17 (4): 429–433. PMID 13406032.
  41. ^ a b Solms H (August 1956). "Chemische Struktur und Psychose bei Lysergsäure-Derivaten" [Chemical structure and lysergic acid derivative psychoses]. Praxis (in German). 45 (32): 746–749. PMID 13359249.
  42. ^ a b Oberlender RA (May 1989). "Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens". Purdue e-Pubs. Purdue University. Table 2. Relative potency values for lysergic acid amides. [...]
  43. ^ Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M.
  44. ^ DeKorne J (1994). "8. d-Lysergic Acid Amide: Morning Glory Seeds, Stipa robusta". Psychedelic shamanism: the cultivation, preparation and shamanic use of psychotropic plants. Port Townsend, Wash: Loompanics Unlimited. p. 81. ISBN 978-1-55950-110-1.
  45. ^ Cole KA (17 August 2013). "Ergot Wine Revisited - YouTube". Neurosoup. Archived from the original on 23 July 2021.
  46. ^ a b Schultes RE, Hofmann A (1973). The Botany and Chemistry of Hallucinogens. Springfield, IL: Charles Thomas. pp. 246, 252. ISBN 9780398064167. Later, it was found that ergine and isoergine were present in the seeds to some extent in the form of lysergic acid N-(1-hydroxyethyl) amide and isolysergic acid N-(1-hydroxyethyl) amide, respectively, and that, during the isolation procedure, they easily hydrolize to ergine and isoergine, respectively, and acetaldehyde.
  47. ^ a b c Sewell RA (2008). "Unauthorized research on cluster headache" (PDF). The Entheogen Review. 16 (4): 117–125.
  48. ^ a b Ingram AL (December 1964). "Morning Glory Seed Reaction". JAMA. 190 (13): 1133–1134. doi:10.1001/jama.1964.03070260045019. PMID 14212309. It has been suggested6 that the insecticide coating on the morning glory seed might be promoting adverse side effects that have been noted. The majority of commercial seeds are treated with N-tri-chlorete which is a fungicide and seed protectant having a tolerance of 100 parts per million.8 Thus, this is quite an inocuous product from the toxicologic point of view and would require ingestion of quantities beyond the capacity of the stomach to absorb, in amounts found as a seed coater, to be considered lethal.9 Symptoms involving the nervous system would be lacking if we were dealing only with the effects of this fungicide. Formerly, compounds containing mercury were used extensively as fungicides and there is the possibility that some seeds so treated might pose a toxicologic danger if ingested. This is considered unlikely as the newer seed protectants have been in use for a considerably longer period than the current morning glory fad. [...] It would seem then, that both the psychological and physiological effects observed in the ingestion of the seed of the morning glory reside in the alkaloids of the seed and not the seed protectant. The LSD-like reaction is most likely due to the LSD-like alkaloids for no pure LSD has as yet been isolated from the seed. As all compounds occurring in the morning glory seed have not been studied intensively enough to inspire confidence in their respective roles, they cannot yet be considered for scientific experimental use much less be used irresponsibly in excitement-seeking self-experimentation.)
  49. ^ a b Kremer C, Paulke A, Wunder C, Toennes SW (January 2012). "Variable adverse effects in subjects after ingestion of equal doses of Argyreia nervosa seeds". Forensic Science International. 214 (1–3): e6 – e8. doi:10.1016/j.forsciint.2011.06.025. PMID 21803515.
  50. ^ a b Nowak J, Woźniakiewicz M, Klepacki P, Sowa A, Kościelniak P (May 2016). "Identification and determination of ergot alkaloids in Morning Glory cultivars". Analytical and Bioanalytical Chemistry. 408 (12): 3093–3102. doi:10.1007/s00216-016-9322-5. PMC 4830885. PMID 26873205See Table 3. [...] Concentration values for "LSH", "Lyzergol/isobars", penniclavine, and chanoclavine can be obtained by dividing the concentration values of ergine or ergometrine by their relative abundance values and multiplying that number by the relative abundance value of the specified chemical.{{cite journal}}: CS1 maint: postscript (link)
  51. ^ a b Schardl CL, Panaccione DG, Tudzynski P (2006). "Ergot alkaloids--biology and molecular biology". The Alkaloids. Chemistry and Biology. 63. Elsevier: 45–86 (50). doi:10.1016/s1099-4831(06)63002-2. ISBN 978-0-12-469563-4. PMID 17133714. Clavines are thought to contribute substantially to convulsive ergotism, since C. fusiformis ergots, which possess clavines, but no [lysergic acid] or lysergyl amides, cause convulsive symptoms (26). However, the ergopeptines are known to produce similar symptoms, and are also thought to cause gangrenous ergotism (6). The occurrence of convulsive ergotism without dry gangrene suggests that other clavine or lysergyl alkaloids are involved, or that individual effects of specific ergopeptines may give clinically different syndromes (6).
  52. ^ a b c d Eich E (January 12, 2008). "4.2 Ergolines". Solanaceae and convolvulaceae - secondary metabolites: biosynthesis, chemotaxonomy, biological and economic significance: a handbook. Berlin, Heidelberg: Springer-Verlag. pp. 225–227, 236, 238, 249, 274. doi:10.1007/978-3-540-74541-9. ISBN 978-3-540-74540-2. OCLC 195613136. Containing ergosine: Argyreia luzonensis, A. mollis, A. obtusifolia, A. philippinensis, A. ridleyi, A. splendens [...] Ipomoea argyrophylla (ergosine and ergobalansine) [...] Table 4.1 Unambiguously ergoline-positive Ipomoea species [...] Table 4.4 Unambiguously ergoline-positive Argyreia species [...]
  53. ^ Beaulieu WT, Panaccione DG, Hazekamp CS, mckee MC, Ryan KL, Clay K (July 2013). "Differential allocation of seed-borne ergot alkaloids during early ontogeny of morning glories (Convolvulaceae)". Journal of Chemical Ecology. 39 (7): 919–930. doi:10.1007/s10886-013-0314-z. PMID 23835852. Ipomoea amnicola and I. argillicola contain ergobalansine [...]
  54. ^ a b Paulke A, Kremer C, Wunder C, Wurglics M, Schubert-Zsilavecz M, Toennes SW (April 2015). "Studies on the alkaloid composition of the Hawaiian Baby Woodrose Argyreia nervosa, a common legal high". Forensic Science International. 249: 281–293. doi:10.1016/j.forsciint.2015.02.011. PMID 25747328. On the other hand, methylergometrine, methysergide, and lysergylalanine were detected, which have not yet been reported as compounds of Argyreia nervosa seeds. Furthermore, some high molecular weight ergot alkaloid derivatives and hydroxyalanine derived ergopeptide fragments could be observed at various retention times (c.f. chapter 3.1). Altogether, lysergylalanine, the high molecular weight ergot alkaloids and the hydroxyalanine derived ergopeptide fragments strongly suggest the presence of ergopeptides in Argyreia nervosa. However, due to the disadvantage of the applied APCI technique for peptide analysis (c.f. chapter 3.1) additional research (e.g. ESI-HRMS/MS) will be necessary to verify this assumption and to elucidate the structure of the ergopeptides." (3. Results and discussion, p. 283) [...]
  55. ^ Bigwood J, Ott J, Thompson C, Neely P (January 1979). "Entheogenic effects of ergonovine". Journal of Psychedelic Drugs. 11 (1–2): 147–149. doi:10.1080/02791072.1979.10472099. PMID 522166.
  56. ^ a b Cohen S (April 1964). "Suicide Following Morning Glory Seed Ingestion". The American Journal of Psychiatry. 120 (1): 1024–1025. doi:10.1176/ajp.120.10.1024. PMID 14138842.
  57. ^ Klinke HB, Müller IB, Steffenrud S, Dahl-Sørensen R (April 2010). "Two cases of lysergamide intoxication by ingestion of seeds from Hawaiian Baby Woodrose". Forensic Science International. 197 (1–3): e1 – e5. doi:10.1016/j.forsciint.2009.11.017. PMID 20018470.
  58. ^ Bendz G, Santesson J, eds. (2013-10-14) [1973]. Chemistry in Botanical Classification: Medicine and Natural Sciences: Medicine and Natural Sciences. Elsevier. p. 235. ISBN 978-0-323-16251-7. Among the most striking characteristics of the family is the occurrence of rows of secretory cells with milky, resinous contents. Resin glycosides are among the most important chemical characteristics of the family. The occurrence of tropine alkaloids in Convolvulus species and lysergic acid type alkaloids in Ipomoea and Rivea species as well as a wide distribution of cinnamic acid derivatives and coumarins are also noteworthy. The last two groups of compounds are common to both the Convolvulaceae and Solanaceae families.
  59. ^ Ono M (October 2017). "Resin glycosides from Convolvulaceae plants". Journal of Natural Medicines. 71 (4): 591–604. doi:10.1007/s11418-017-1114-5. PMC 6763574. PMID 28748432.
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  61. ^ Peter Jordan. Re: Woodrose vs Ipomoea. alt.drugs, UseNet, 10/1/1994 https://erowid.org/plants/hbw/hbw_info1.shtml
  62. ^ Mann J, ed. (1973). The First Book of Sacraments of the Church of the Tree of Life: A Guide for the Religious Use of Legal Mind Alterants. San Francisco, CA: Tree of Life Press. p. 13. The standard procedure is to scrape or singe the white layer from the seed coat before grinding. This layer is believed to contain a strychnine-like alkaloid which may cause undesirable symptoms.
  63. ^ Pendell D (28 September 2010) [2005]. Pharmako/Gnosis: Plant Teachers and the Poison Path (Revised and Updated ed.). North Atlantic Books. p. 106. ISBN 9781556438042. To put one persistent myth to rest, there is no strychnine in peyote. The white fuzz that is usually removed from the buttons before ingestion can be a gastroirritant, but it does not contain strychnine. However, lophophorine, accounting for about 0.18% of the dry weight of the buttons, can cause some symptoms similar to strychnine poisoning, such as a sickening feeling in the back of the head, and hotness and blushing of the face. Lophophorine causes violent convulsions when injected into rabbits at concentrations of 12 milligrams per kilogram of body weight.
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Allikas: https://en.wikipedia.org/wiki/Ergine
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