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Ergine

(Redirected from Isoergine)

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]

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)

Occurrence in nature

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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

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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

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Pharmacodynamics

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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

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History

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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

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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

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

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History

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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

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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]

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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

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References

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  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.
  6. ^ "Erowid Morning Glory Basics". Erowid.org. Retrieved 2012-02-03.
  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 (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  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.
  10. ^ 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.
  11. ^ Shulgin A. "#26. LSD-25". TiHKAL. Erowid.org. Retrieved 2012-02-03.
  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.
  13. ^ Flieger M, Sedmera P, Vokoun J, R̆ic̄icovā A, R̆ehác̆ek Z (1982-02-19). "Separation of four isomers of lysergic acid α-hydroxyethylamide by liquid chromatography and their spectroscopic identification". Journal of Chromatography A. 236 (2): 441–452. doi:10.1016/S0021-9673(00)84895-5. ISSN 0021-9673.
  14. ^ Ramstad E (1968). "Chemistry of alkaloid formation in ergot". Lloydia. 31: 327–341.
  15. ^ Kleinerová E, Kybal J (September 1973). "Ergot alkaloids. IV. Contribution to the biosynthesis of lysergic acid amides". Folia Microbiologica. 18 (5): 390–392. doi:10.1007/BF02875934. PMID 4757982.
  16. ^ Panaccione DG, Tapper BA, Lane GA, Davies E, Fraser K (October 2003). "Biochemical outcome of blocking the ergot alkaloid pathway of a grass endophyte". Journal of Agricultural and Food Chemistry. 51 (22) (published 2003-10-01): 6429–6437. Bibcode:2003JAFC...51.6429P. doi:10.1021/jf0346859. PMID 14558758.
  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.
  19. ^ Schultes RE, Hofmann A (1973). The Botany and Chemistry of Hallucinogens. Springfield, IL: Charles Thomas. ISBN 9780398064167.
  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.
  21. ^ Petroski RJ, Powell RG, Clay K (March–April 1992). "Alkaloids of Stipa robusta (sleepygrass) infected with an Acremonium endophyte". Natural Toxins. 1 (2): 84–88. doi:10.1002/nt.2620010205. PMID 1344912.
    “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.
  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.
  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.
  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.
  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.
  34. ^ Alderman SC, Halse RR, White JF (January 2004). "A Reevaluation of the Host Range and Geographical Distribution of Claviceps Species in the United States". Plant Disease. 88 (1): 63–81. doi:10.1094/PDIS.2004.88.1.63. PMID 30812458.
  35. ^ Petroski RJ, Powell RG, Clay K (March–April 1992). "Alkaloids of Stipa robusta (sleepygrass) infected with an Acremonium endophyte". Natural Toxins. 1 (2): 84–88. doi:10.1002/nt.2620010205. PMID 1344912.
  36. ^ Miles CO, Lane GA, di Menna ME, Garthwaite I, Piper EL, Ball OJ, et al. (1996-05-16). "High Levels of Ergonovine and Lysergic Acid Amide in Toxic Achnatherum inebrians Accompany Infection by an Acremonium -like Endophytic Fungus". Journal of Agricultural and Food Chemistry. 44 (5): 1285–1290. Bibcode:1996JAFC...44.1285M. doi:10.1021/jf950410k. ISSN 0021-8561.
  37. ^ Petroski RJ, Powell RG (1991-01-09). "Preparative Separation of Complex Alkaloid Mixture by High-Speed Countercurrent Chromatography". In Hedin PA (ed.). Naturally Occurring Pest Bioregulators. ACS Symposium Series. Vol. 449. Washington, DC: American Chemical Society. pp. 426–434. doi:10.1021/bk-1991-0449.ch031. ISBN 978-0-8412-1897-0.
  38. ^ Chen L, Li X, Li C, Swoboda GA, Young CA, Sugawara K, et al. (July 2015). "Two distinct Epichloë species symbiotic with Achnatherum inebrians, drunken horse grass". Mycologia. 107 (4): 863–873. doi:10.3852/15-019. PMID 25911697.
  39. ^ a b c d e Leadmon CE, Sampson JK, Maust MD, Macias AM, Rehner SA, Kasson MT, et al. (July 2020). Alexandre G (ed.). "Several Metarhizium Species Produce Ergot Alkaloids in a Condition-Specific Manner". Applied and Environmental Microbiology. 86 (14) (published 2020-07-02). Bibcode:2020ApEnM..86E.373L. doi:10.1128/AEM.00373-20. PMC 7357478. PMID 32385081.
  40. ^ a b c Jones AM, Steen CR, Panaccione DG (November 2021). Atomi H (ed.). "Independent Evolution of a Lysergic Acid Amide in Aspergillus Species". Applied and Environmental Microbiology. 87 (24) (published 2021-11-24): e0180121. Bibcode:2021ApEnM..87E1801J. doi:10.1128/AEM.01801-21. PMC 8612279. PMID 34586904.
  41. ^ Lorenz N, Haarmann T, Pazoutová S, Jung M, Tudzynski P (2009-10-01). "The ergot alkaloid gene cluster: functional analyses and evolutionary aspects". Phytochemistry. Evolution of Metabolic Diversity. 70 (15–16): 1822–1832. Bibcode:2009PChem..70.1822L. doi:10.1016/j.phytochem.2009.05.023. PMID 19695648.
  42. ^ Fleetwood DJ, Scott B, Lane GA, Tanaka A, Johnson RD (April 2007). "A complex ergovaline gene cluster in epichloe endophytes of grasses". Applied and Environmental Microbiology. 73 (8) (published 2007-04-15): 2571–2579. Bibcode:2007ApEnM..73.2571F. doi:10.1128/AEM.00257-07. PMC 1855613. PMID 17308187.
  43. ^ Schardl CL, Leuchtmann A, Spiering MJ (2004-06-02). "Symbioses of grasses with seedborne fungal endophytes". Annual Review of Plant Biology. 55 (1): 315–340. doi:10.1146/annurev.arplant.55.031903.141735. PMID 15377223.
  44. ^ a b c d e f g h i j k l m n Kozlovsky AG (2006). "18. Producers of ergot alkaloids out of Claviceps genus". In Křen V, Cvak L (eds.). Ergot: The Genus Claviceps. Medicinal and aromatic plants - industrial profiles. London: Harwood Academic Publishers. ISBN 978-90-5702-375-0.
  45. ^ a b c d e Schardl CL, Young CA, Hesse U, Amyotte SG, Andreeva K, Calie PJ, et al. (2013-02-28). Heitman J (ed.). "Plant-symbiotic fungi as chemical engineers: multi-genome analysis of the clavicipitaceae reveals dynamics of alkaloid loci". PLOS Genetics. 9 (2): e1003323. doi:10.1371/journal.pgen.1003323. PMC 3585121. PMID 23468653.
  46. ^ a b Charlton ND, Craven KD, Afkhami ME, Hall BA, Ghimire SR, Young CA (October 2014). "Interspecific hybridization and bioactive alkaloid variation increases diversity in endophytic Epichloë species of Bromus laevipes". FEMS Microbiology Ecology. 90 (1) (published 2014-10-01): 276–289. Bibcode:2014FEMME..90..276C. doi:10.1111/1574-6941.12393. PMID 25065688.
  47. ^ a b c d e f Schardl CL, Young CA, Pan J, Florea S, Takach JE, Panaccione DG, et al. (June 2013). "Currencies of mutualisms: sources of alkaloid genes in vertically transmitted epichloae". Toxins. 5 (6) (published June 6, 2013): 1064–1088. doi:10.3390/toxins5061064. PMC 3717770. PMID 23744053.
  48. ^ Charlton ND, Craven KD, Mittal S, Hopkins AA, Young CA (Sep–Oct 2012). "Epichloe canadensis, a new interspecific epichloid hybrid symbiotic with Canada wildrye (Elymus canadensis)". Mycologia. 104 (5): 1187–1199. doi:10.3852/11-403. PMID 22675049.
  49. ^ a b Takach JE, Mittal S, Swoboda GA, Bright SK, Trammell MA, Hopkins AA, et al. (August 2012). "Genotypic and chemotypic diversity of Neotyphodium endophytes in tall fescue from Greece". Applied and Environmental Microbiology. 78 (16) (published 2012-08-15): 5501–5510. Bibcode:2012ApEnM..78.5501T. doi:10.1128/AEM.01084-12. PMC 3406137. PMID 22660705.
  50. ^ Hanigan MH, Ricketts WA (June 1993). "Extracellular glutathione is a source of cysteine for cells that express gamma-glutamyl transpeptidase". Biochemistry. 32 (24): 6302–6306. doi:10.1021/bi00075a026. PMID 8099811.
  51. ^ a b c Young CA, Charlton ND, Takach JE, Swoboda GA, Trammell MA, Huhman DV, et al. (2014-11-04). "Characterization of Epichloë coenophiala within the US: are all tall fescue endophytes created equal?". Frontiers in Chemistry. 2: 95. Bibcode:2014FrCh....2...95Y. doi:10.3389/fchem.2014.00095. PMC 4219521. PMID 25408942.
  52. ^ Fleetwood DJ, Scott B, Lane GA, Tanaka A, Johnson RD (April 2007). "A complex ergovaline gene cluster in epichloe endophytes of grasses". Applied and Environmental Microbiology. 73 (8) (published 2007-04-15): 2571–2579. Bibcode:2007ApEnM..73.2571F. doi:10.1128/AEM.00257-07. PMC 1855613. PMID 17308187.
  53. ^ Fleetwood DJ, Khan AK, Johnson RD, Young CA, Mittal S, Wrenn RE, et al. (2011-01-01). "Abundant degenerate miniature inverted-repeat transposable elements in genomes of epichloid fungal endophytes of grasses". Genome Biology and Evolution. 3: 1253–1264. doi:10.1093/gbe/evr098. PMC 3227409. PMID 21948396.
  54. ^ Panaccione DG, Johnson RD, Wang J, Young CA, Damrongkool P, Scott B, et al. (October 2001). "Elimination of ergovaline from a grass-Neotyphodium endophyte symbiosis by genetic modification of the endophyte". Proceedings of the National Academy of Sciences of the United States of America. 98 (22) (published 2001-10-23): 12820–12825. Bibcode:2001PNAS...9812820P. doi:10.1073/pnas.221198698. PMC 60137. PMID 11592979.
  55. ^ Young CA, Schardl CL, Panaccione DG, Florea S, Takach JE, Charlton ND, et al. (April 2015). "Genetics, genomics and evolution of ergot alkaloid diversity". Toxins. 7 (4) (published 2015-04-16): 1273–1302. doi:10.3390/toxins7041273. PMC 4417967. PMID 25875294. See table 3 on p. 1290.
  56. ^ Shymanovich T, Saari S, Lovin ME, Jarmusch AK, Jarmusch SA, Musso AM, et al. (January 2015). "Alkaloid variation among epichloid endophytes of sleepygrass (Achnatherum robustum) and consequences for resistance to insect herbivores". Journal of Chemical Ecology. 41 (1) (published 2014-12-11): 93–104. Bibcode:2015JCEco..41...93S. doi:10.1007/s10886-014-0534-x. PMID 25501262.
  57. ^ Christensen M, Leuchtmann A, Rowan D, Tapper B (1993-09-01). "Taxonomy of Acremonium endophytes of tall fescue (Festuca arundinacea), meadow fescue (F. pratensis) and perennial ryegrass (Lolium perenne)". Mycological Research. 97 (9): 1083–1092. doi:10.1016/S0953-7562(09)80509-1.
  58. ^ Panaccione DG, Johnson RD, Wang J, Young CA, Damrongkool P, Scott B, et al. (October 2001). "Elimination of ergovaline from a grass-Neotyphodium endophyte symbiosis by genetic modification of the endophyte". Proceedings of the National Academy of Sciences of the United States of America. 98 (22) (published 2001-10-23): 12820–12825. Bibcode:2001PNAS...9812820P. doi:10.1073/pnas.221198698. PMC 60137. PMID 11592979.
  59. ^ Hofmann A (1963). "The Active Principles of the Seeds of Rivea corymbosa and Ipomoea violacea". Harvard Botanical Museum Leaflets. 20 (6): 208–209
    This plant is now considered to be Ipomoea tricolor.    {{cite journal}}: CS1 maint: postscript (link)
  60. ^ 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.
  61. ^ Heim E, Heimann H, Lukács G (1968). "Die psychische Wirkung der mexikanischen Droge „Ololiuqui" am Menschen". Psychopharmacologia (in German). 13 (1): 35–48. doi:10.1007/BF00401617. PMID 5675457
    The quotes on this page were translated w/ Google Translate.    {{cite journal}}: CS1 maint: postscript (link)
  62. ^ Schultes RE, Hofmann A (1973). "Convolvulaceae". The Botany and Chemistry of Hallucinogens. Springfield, IL: Charles Thomas. p. 252. ISBN 9780398064167.
  63. ^ Hofmann A (1980). "3. Chemical Modifications of LSD". LSD, My Problem Child. New York: McGraw-Hill. ISBN 978-0-07-029325-0.
  64. ^ Grof S, Hofmann A (Fall 2001) [1984]. "Stanislav Grof Interviews Dr. Albert Hofmann". MAPS Bulletin. 9 (2): 22–35.{{cite journal}}: CS1 maint: date and year (link)
  65. ^ a b c Paulke A, Kremer C, Wunder C, Achenbach J, Djahanschiri B, Elias A, et al. (July 2013). "Argyreia nervosa (Burm. f.): receptor profiling of lysergic acid amide and other potential psychedelic LSD-like compounds by computational and binding assay approaches". Journal of Ethnopharmacology. 148 (2): 492–497. doi:10.1016/j.jep.2013.04.044. PMID 23665164.
  66. ^ Wacker D, Wang S, McCorvy JD, Betz RM, Venkatakrishnan AJ, Levit A, et al. (January 2017). "Crystal Structure of an LSD-Bound Human Serotonin Receptor". Cell. 168 (3): 377–389.e12. doi:10.1016/j.cell.2016.12.033. PMC 5289311. PMID 28129538.
  67. ^ Halberstadt AL, Nichols DE (2020). "Serotonin and serotonin receptors in hallucinogen action". Handbook of the Behavioral Neurobiology of Serotonin. Handbook of Behavioral Neuroscience. Vol. 31. pp. 843–863. doi:10.1016/B978-0-444-64125-0.00043-8. ISBN 9780444641250. ISSN 1569-7339.
  68. ^ 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. ISSN 0368-1769.
  69. ^ a b c d e f Gerhards N, Neubauer L, Tudzynski P, Li SM (December 2014). "Biosynthetic pathways of ergot alkaloids". Toxins. 6 (12): 3281–3295. doi:10.3390/toxins6123281. PMC 4280535. PMID 25513893.
  70. ^ a b c Willingale J, Atwell SM, Mantle PG (1983-07-01). "Unusual Ergot Alkaloid Biosynthesis in Sclerotia of a Claviceps purpurea Mutant". Microbiology. 129 (7): 2109–2115. doi:10.1099/00221287-129-7-2109. ISSN 1350-0872.
  71. ^ DeKorne J. "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.
  72. ^ Cole KA. "Ergot Wine Revisited - YouTube". web.archive.org. Neurosoup.
  73. ^ a b c Sewell RA (2008). "Unauthorized research on cluster headache" (PDF). The Entheogen Review. 16 (4): 117–125.
  74. ^ Schultes RE (1941). A Contribution to Our Knowledge of Rivea Corymbosa: The Narcotic Ololinqui of the Aztecs (1st ed.). Botanical Museum of Harvard University.
  75. ^ Wasson RG (1961). The Hallucinogenic Fungi Of Mexico: An Inquiry Into The Origins of The Religious Idea Among Primitive Peoples. Archived from the original on 22 November 2010. Retrieved 27 November 2024.
  76. ^ "Project Mkultra, Subproject 22 (w/attachments)". Central Intelligence Agency.
  77. ^ Ingram AL (December 1964). "Morning Glory Seed Reaction". JAMA. 190 (13) (13 ed.): 1133–1134. doi:10.1001/jama.1964.03070260045019. PMID 14212309.
  78. ^ 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.
  79. ^ 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.
  80. ^ 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.
  81. ^ "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.
  82. ^ "Erowid LSA Vault : Legal Status". erowid.org. Retrieved 2020-05-05.

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