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Ergine

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Ergine
Clinical data
Other namesLAA[1][2][3][4][5], ᴅ-lysergic acid amide, ᴅ-lysergamide, ergine, LA-111, “LSA”
Pregnancy
category
Routes of
administration		Oral, intramuscular injection
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
MetabolismHepatic
ExcretionRenal
Identifiers
  • (8β)-9,10-didehydro-6-methyl-
    ergoline-8-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.841 Edit this at Wikidata
Chemical and physical data
FormulaC16H17N3O
Molar mass267.332 g·mol−1
3D model (JSmol)
Melting point135 °C (275 °F) Decomposes[9]
  • O=C(N)[C@@H]1C=C2C3=CC=CC4=C3C(C[C@@]2([H])N(C1)C)=CN4
  • InChI=1S/C16H17N3O/c1-19-8-10(16(17)20)5-12-11-3-2-4-13-15(11)9(7-18-13)6-14(12)19/h2-5,7,10,14,18H,6,8H2,1H3,(H2,17,20)/t10-,14-/m1/s1 checkY
  • Key:GENAHGKEFJLNJB-QMTHXVAHSA-N checkY
  (verify)

Ergine, also known as lysergic acid amide and lysergamide, is an ergoline alkaloid that occurs in various species of vines of the Convolvulaceae and some species of fungi. The psychedelic properties in the seeds of ololiuhqui, Hawaiian baby woodrose and morning glories have been linked to ergine and/or isoergine, its epimer, as it is an alkaloid present in the seeds.[10][11][12]

Occurrence in nature

[edit]

Ergine is not a biosynthetic endpoint itself, but rather a hydrolysis product of lysergic acid hydroxyethylamide (LAH), lysergic acid hydroxymethylethylamide (ergonovine), and ergopeptines or their ergopeptam precursors.[13][14][15][16][17]

Lysergic acid hydroxyethylamide is very vulnerable to this hydrolysis,[18][19] and many analyses of ergoline-containing fungi show little to no LAH and substantial amounts of ergine.

An ergine analog, 8-hydroxyergine, has also been found in natural products in two studies.[20][21] Methylergonovine and methylmethylergonovine (methysergide) have also been found in a natural product in only one study;[22] these are documented as semisynthetic chemicals, so the findings need to be repeated for certainty. The aforementioned chemicals are the only natural ergoamides.

LAH & ergine are predominant in Claviceps paspali,[23][24][25] but are only found in trace amounts in the more well-known Claviceps purpurea[26][27] (both are ergot-spreading fungi). The major products of C. purpurea are ergopeptines, but C. paspali does not generate ergopeptines.[28] Ergonovine is the only ergoamide in C. purpurea in a substantial amount.[29]

LAH & 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[30] (ergolines have been identified in 42 of these plants and not all of them contain ergine[31]). Ergonovine is present in Ipomoea tricolor in one-tenth to one-third of the amount of ergine.[32] This variable may account for the varying reports about the psychedelic effect of these seeds.[33]

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

  • Unidentified Acremonium species that infects sleepy grass (C. purpurea also infects sleepy grass[34]).[35]
  • Unidentified Acremonium species that infects drunken horse grass[36]
  • Acremonium coenophialum (infects Festuca arundinacea)[37]
  • Epichloë gansuensis var. inebriens (infects drunken horse grass)[38]
  • Metarhizium brunneum[39]
  • Metarhizium acridum[39]
  • Metarhizium anisopliae[39]
  • Metarhizium flavoviride[39]
  • Metarhizium robertsii[39]
  • Aspergillus leporis[40]
  • Aspergillus homomorphus[40]
  • Aspergillus hancockii[40]

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[41]
  • Neotyphodium lolii[42]
  • Unidentified Epichlöe and Neotyphodium (asexual forms of Epichlöe) species[43]
  • Aspergillus fumigata[44]
  • Aspergillus flavus[44]
  • Botritis fabae[44]
  • Curvularia lunata[44]
  • Geotrichum candidum[44]
  • Balansia cyperi[44]
  • Balansia claviceps[44]
  • Balansia epichloë[44]
  • Epichloë amarillans[45]
  • Epichloë cabralii (H)[46]
  • Epichloë canadensis (H)[47][48]
  • Epichloë coenophiala (H)[47][49][50][51]
  • Epichloë festucae[45]
  • Epichloë festucae var. lolii[52][53]
  • Epichloë festucae var. lolii x E. typhina (H)[47][54]
  • Epichloë inebriens[45]
  • Epichloë glyceriae[45]
  • Epichloë mollis[47]
  • Epichloë typhina[44]
  • Epichloë typhina ssp. poae[45][46]
  • Epichloë typhina ssp. clarkii[55]
  • Epichloë sp. AroTG-2(H)[56]
  • Epichloë sp. FaTG-2(H)[47][49][51][57][58]
  • Epichloë sp. FaTG-4(H)[47][51]
  • Hypomyces aurantius[44]
  • Sepedonium sp.[44]
  • Cunnigbamella blakesleana[44]
  • Mucor biemalis[44]
  • Rhizopus nigricans[44]

Psychedelic Effects

[edit]

Ergine has only been given a miniscule amount of attention. Albert Hofmann and his colleagues self-administered ergine,[59] and it was adminstered in two clinical trials.[60][61] Synthetic ergine was used in all cases. Albert 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.” There are parallels between Hofmann's comments and the ones in the two trials:

Hofmann 1963 Heim 1968 Solms 1956
“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:

“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).”[62]

“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.”[63]

“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.”[64]

Pharmacology

[edit]

Pharmacodynamics

[edit]
Affinities of LSA and LSD for various receptors[65]
Receptor Affinity (Ki [nM])
LSA LSD
5-HT1A 10 2.5
5-HT2 28 0.87
D1 832 87
D2L 891 155
D2S 145 25
D3 437 65
D4.4 141 30
α1 912 60
α2 62 1.0
Notes: 5-HT1A and D1 are for pig receptors.[65]

Ergine interacts with serotonin, dopamine, and adrenergic receptors similarly to but with lower affinity than lysergic acid diethylamide (LSD).[65][66] 

The psychedelic effects of ergine can be attributed to activation of serotonin 5-HT2A receptors.[67]

Chemistry

[edit]

History

[edit]

Ergine was first obtained by Sidney Smith and Geoffrey Willward Timmis in 1932.[68]

Albert Hofmann was first to identify ergine as a natural constituent of Turbina corymbosa seeds.[12]

Biosynthesis

[edit]
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.[69] 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).[69] 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.[69][70]

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.[69][70] 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.[69] 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.[69][70]

Use of Morning Glory seeds as a drug

[edit]

History

[edit]

Ololiuhqui was used by South American healers in shamanic healing ceremonies.[73] 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.[74][73]

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.[75]

The Central Intelligence Agency conducted research on the psychedelic properties of Rivea corymbosa seeds for MKULTRA.[76]

Physiological effects

[edit]

While its physiological effects vary from person to person, the following symptoms have been attributed to the consumption of ergine or ergine containing seeds:[12][73][77]

One study found that 2 of 4 human subjects experienced cardiovascular dysregulation and the study had to be halted, concluding that the ingestion of seeds containing ergine was less safe then 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.[78]

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.[79] Another instance is a death due to falling off of a building after ingestion of Hawaiian baby woodrose seeds and alcohol.[80]

A study gave mice 3000 mg/kg with no lethal effects.[citation needed]

[edit]

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

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.[81] Similarly, ergine is considered a Class A substance in the United Kingdom, categorized as a precursor to LSD.

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

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.[82]

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.

See also

[edit]

References

[edit]
  1. ^ Oliver JW, Abney LK, Strickland JR, Linnabary RD (1993-10-01). "Vasoconstriction in bovine vasculature induced by the tall fescue alkaloid lysergamide2". Journal of Animal Science. 71 (10): 2708–2713. doi:10.2527/1993.71102708x. ISSN 0021-8812.
  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. ISSN 0013-0001.
  3. ^ Genest K (1966-11-01). "Changes in Ergoline Alkaloids in Seeds During Ontogeny of Ipomoea violacea". Journal of Pharmaceutical Sciences. 55 (11): 1284–1288. doi:10.1002/jps.2600551123. ISSN 0022-3549.
  4. ^ Genest K (1965-01-01). "A direct densitometric method on thin-layer plates for the determination of lysergic acid amide, isolysergic acid amide and clavine alkaloids in morning glory seeds". Journal of Chromatography A. 19: 531–539. doi:10.1016/S0021-9673(01)99495-6. ISSN 0021-9673.
  5. ^ Brown JK, Malone MH (1978-01-01). ""Legal Highs"–Constituents, Activity, Toxicology, and Herbal Folklore". Clinical Toxicology. 12 (1): 1–31. doi:10.3109/15563657809149579. ISSN 0009-9309. PMID 343978.
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  8. ^ "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.
  9. ^ Smith S, Timmis GM (1932). "98. The alkaloids of ergot. Part III. Ergine, a new base obtained by the degradation of ergotoxine and ergotinine". Journal of the Chemical Society (Resumed): 763. doi:10.1039/jr9320000763.
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  12. ^ a b c Hofmann A (2009). LSD My Problem Child: Reflections on Sacred Drugs, Mysticism, and Science (4th ed.). MAPS.org. ISBN 978-0979862229.
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  17. ^ Panaccione DG (2010). "Ergot alkaloids". In Hofrichter M (ed.). The Mycota, Industrial Applications. Vol. 10 (2nd ed.). Berlin-Heidelburg, Germany: Springer-Verlag. pp. 195–214.
  18. ^ Shulgin A (1976). "4. Psychotomimetic Agents". In Maxwell G (ed.). Psychopharmacological agents. Medicinal Chemistry. Vol. 4. New York: Academic Press. pp. 59–00. ISBN 978-0-12-290559-9
    “The monohydroxyethylamides of each of these two materials are also principal components of the various morning glorys; viz., lysergic acid-α-hydroxyethylamide (VIII) and isolysergic acid-α-hydroxyethylamide (XI). These two carbinolamides are the principal ergot products of culture medium synthesis from Claviceps paspali, from which they can be prepared in concentrations of grams per liter of culture medium. 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. In these instances their presence will be measured only by the elevated levels of the derived amides.” B. Lysergamides from the Convolvulaceae spp.: 1. Botany and Chemistry, pages 71 & 72    {{cite book}}: CS1 maint: postscript (link)
  19. ^ Schultes RE, Hofmann A (1973). The Botany and Chemistry of Hallucinogens. Springfield, IL: Charles Thomas. 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.” 4. Plants of Hallucinogenic Use: Convolvulaceae, p. 246    {{cite book}}: CS1 maint: postscript (link)
  20. ^ Flieger M, Linhartová R, Sedmera P, Zima J, Sajdl P, Stuchlík J, et al. (September 1, 1989). "New Alkaloids of Claviceps paspali". Journal of Natural Products. 52 (5): 1003–1007. doi:10.1021/np50065a014. ISSN 0163-3864.
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    “8-Hydroxylysergic acid amide was isolated with difficulty as it was present as only a minor alkaloid in endophyte-infected sleepygrass (0.3 pg/g dry wt).” Results and Discussion, p. 87
  22. ^ 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 (published March 10, 2015): 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.” 3. Results and Discussion, p. 283
  23. ^ Arcamone F, Bonino C, Chain EB, Ferretti A, Pennella P, Tonolo A, et al. (July 1960). "Production of lysergic acid derivatives by a strain of Claviceps paspali Stevens and Hall in submerged culture". Nature. 187 (4733): 238–239. Bibcode:1960Natur.187..238A. doi:10.1038/187238a0. PMID 13794048.
  24. ^ Castagnoli N, Corbett K, Chain EB, Thomas R (April 1970). "Biosynthesis of N-(alpha-hydroxyethyl) lysergamide, a metabolite of Claviceps paspali Stevens and Hall". The Biochemical Journal. 117 (3) (published 1970-04-01): 451–455. doi:10.1042/bj1170451. PMC 1178946. PMID 5419742.
  25. ^ Basmadjian G, Floss HG, Gröger D, Erge D (1969). "Biosynthesis of ergot alkaloids. Lysergylalanine as precursor of amide-type alkaloids". J. Chem. Soc. D (8): 418–419. doi:10.1039/C29690000418. ISSN 0577-6171.
  26. ^ Schultes R (1973). "4. Plants of Hallucinogenic Use / The Fungi". The Botany and Chemistry of Hallucinogens. Springfield, IL: Charles Thomas. p. 37. ISBN 9780398064167. Whereas ergine, lysergic acid hydroxyethylamide, and lysergyl L-valine methylester occur in ergot of rye only in trace amounts, ergonovine (synonyms ergometrine, ergobasin), which is the specific oxytocic factor of a ergot, is often found in remarkable quantities. In contrast, ergine and hydroxyethylamide of lysergic acid are the main constituents of certain ergot growing on wild grasses, e.g. Paspalum distichum.
  27. ^ Wasson RG, Hofmann A, Ruck CA, Webster P (November 25, 2008). Forte R (ed.). The Road to Eleusis: Unveiling the Secret of the Mysteries (30th Anniversary ed.). Berkeley, Calif.: North Atlantic Books. ISBN 978-1-55643-752-6. We analyzed ergot of wheat and ergot of barley in our laboratory and they were found to contain basically the same alkaloids as ergot of rye, viz. alkaloids of the ergotamine and ergotoxine group, ergonovine, and sometimes also traces of lysergic acid amide. As I said before, ergonovine and lysergic acid amide, both psychoactive, are soluble in water whereas the other alkaloids are not." 2. A Challenging Question and My Answer, p. 42 (Hofmann)
  28. ^ Panaccione DG (2010). "Ergot alkaloids". In Hofrichter M (ed.). The Mycota, Industrial Applications. Vol. 10 (2nd ed.). Berlin-Heidelburg, Germany: Springer-Verlag. pp. 195–214. C. paspali produces simple amides of lysergic acid (ergonovine, lysergic acid α-hydroxyethylamide, ergine) but not ergopeptines. Such a profile could be explained by a battery of ergot alkaloid biosynthetic genes similar to those found in C. purpurea but lacking the peptide synthetase LPS1 encoded by lpsA. This explanation is hypothetical because ergot pathway genes have not yet been analyzed in C. paspali." 2. Typical Terminal Branch in Clavicipitaceous Ergot Alkaloid Producers, p. 205
  29. ^ Wasson RG, Hofmann A, Ruck CA, Webster P (November 25, 2008). Forte R (ed.). The Road to Eleusis: Unveiling the Secret of the Mysteries (30th Anniversary ed.). Berkeley, Calif.: North Atlantic Books. ISBN 978-1-55643-752-6. Samples of ergot grown on L. temulentum and L . perenne collected in Germany, France, and Switzerland showed large variation in their alkaloidal composition. Some contained substantial amounts of ergonovine together with alkaloids of the ergotamine and ergotoxine group.2
    “2. Kobel, H., Sandoz Research Laboratories, Basel. Private communication.”
    2. A Challenging Question and My Answer, p. 44 (Hofmann)
  30. ^ Leistner E, Steiner U (February 3, 2018). "The Genus Periglandula and Its Symbiotum with Morning Glory Plants (Convolvulaceae)". In Anke T, Schüffler A (eds.). Physiology and Genetics. Cham: Springer International Publishing. pp. 131–147. doi:10.1007/978-3-319-71740-1_5. ISBN 978-3-319-71739-5. Retrieved 2024-11-21.
  31. ^ 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. doi:10.1007/978-3-540-74541-9. ISBN 978-3-540-74540-2. OCLC 195613136.
    Table 4.1 Unambiguously ergoline-positive Ipomoea species (pages 225-227)
    Table 4.4 Unambiguously ergoline-positive Argyreia species (p. 236)
    Table 4.5 Unambiguously ergoline-positive Stictocardia and Turbina species (p. 238)
  32. ^ 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) (published February 14, 2016): 3093–3102. doi:10.1007/s00216-016-9322-5. PMC 4830885. PMID 26873205
    See table 3.
    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)
  33. ^ 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
    “We experienced low intensity perceptual alterations, if one might call it so, of the surroundings, both natural and man-made, characterized by a sense of spiritual profoundness imbedded in outdoor nature. There was a mild awareness of inner personal spirituality and insight (entheoi), without hallucination or euphoria. The somatic effects consisted primarily of mild leg cramps. As an entheogen, on the whole, ergonovine maleate did not prove so impressive as, for instance, LSD or psilocybin. This may be ascribed to the fact that ergonovine is only one of the psychoactive alkaloids present in ergot. In antiquity, the entire mass of the ergot was used in the preparation of the hallucinogenic potion, in which the combined actions of ergonovine and ergine could enhance the potency of each other and produce a considerably more powerful effect.” Chapter 5: The Ritual Drug Complex: Ethnobiology of Heaven and Hell: Psychoactivity and Mechanisms of Hallucinations, p. 146    {{cite book}}: CS1 maint: postscript (link)
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    “Such a confusing example resulting in numerous false repetitions in studies of other authors has happened already in the first ergoline paper on Ipomoea tricolor Cav. whose seeds are known as “badoh negro”: Together with this correct synonym the species was incorrectly called I. violacea L. (Hofmann 1964) instead of I. violacea auct., non L. This is of importance since I. violacea L. is the currently accepted name of a different Ipomoea species, I. tuba (Schlecht.) G.Don (Austin and Huáman 1996).”
    Eich E (January 12, 2008). "4.2.3 Occurrence in the Convolvulaceae (p. 224)". Solanaceae and Convolvulaceae - Secondary Metabolites: biosynthesis, chemotaxonomy, biological and economic significance: a handbook. Berlin, Heidelberg: Springer-Verlag. doi:10.1007/978-3-540-74541-9. ISBN 978-3-540-74540-2. OCLC 195613136.    {{cite journal}}: CS1 maint: postscript (link)
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    See “LSD Diethylamide Stereoselectivity and Function”, figure 3, and “Discussion” (pages 382, 381, and 385).
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    Krystle discusses the time she drank ergot wine. Ergot (Claviceps purpurea) is thought to be a component of the Kykeon, a hallucinogenic sacrament used by Socrates and others during the Eleusinian Mysteries. It is also a precursor to LSD.
    This video is for harm reduction and educational purposes only. It is not intended to promote the use of any substance, whether legal or illegal...In this series (Flashbacks), Krystle revisits some classic videos by sharing never-before-seen footage and outtakes.
    Note: Rather than using ergot yourself, let this video satisfy your curiosity about the effects of ergot. Remember, ergot is considered a poison and it comes with a ton of negative effects like: seizures, painful muscle spasms, loss of limbs, nausea, and vomiting.
    For a more detailed discussion of the Ergot Wine, see Krystle's book Lysergic -
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Further reading

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