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Ergine

(Redirected from Lysergic acid amide)

Ergine, also known as lysergic acid amide and lysergamide, is an ergoline alkaloid that occurs in Clavicipitaceous fungi, which includes Convolvulaceae vines (Morning Glory), which have a permanent bond with these fungi.[10] The most common source of ergine for consumers is the seeds of Ipomoea tricolor, Ipomoea corymbosa, and Argyreia nervosa;[11][12][13] isoergine[14] and lysergic acid propanolamide[15] have also been shown to contribute to their psychoactivity.

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.[16][17][18][19][20]

Lysergic acid hydroxyethylamide is very vulnerable to this hydrolysis,[21][22] 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.[23][24] Methylergonovine and methylmethylergonovine (methysergide) have also been found in a natural product in only one study;[25] 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,[26][27][28] but are only found in trace amounts in the more well-known Claviceps purpurea[29][30] (both are ergot-spreading fungi). The major products of C. purpurea are ergopeptines, but C. paspali does not generate ergopeptines.[31] Ergonovine is the only ergoamide in C. purpurea in a substantial amount.[32]

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[10] (ergolines have been identified in 42 of these plants and not all of them contain ergine[33]). Ergonovine is present in Ipomoea tricolor in one-tenth to one-third of the amount of ergine.[34] This variable may account for the varying reports about the psychedelic effect of these seeds.[15]

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[35]).[36]
  • Unidentified Acremonium species that infects drunken horse grass[37]
  • Acremonium coenophialum (infects Festuca arundinacea)[38]
  • Epichloë gansuensis var. inebriens (infects drunken horse grass)[39]
  • Metarhizium brunneum[40]
  • Metarhizium acridum[40]
  • Metarhizium anisopliae[40]
  • Metarhizium flavoviride[40]
  • Metarhizium robertsii[40]
  • Aspergillus leporis[41]
  • Aspergillus homomorphus[41]
  • Aspergillus hancockii[41]

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[42]
  • Neotyphodium lolii[43]
  • Unidentified Epichlöe and Neotyphodium (asexual forms of Epichlöe) species[44]
  • Aspergillus fumigata[45]
  • Aspergillus flavus[45]
  • Botritis fabae[45]
  • Curvularia lunata[45]
  • Geotrichum candidum[45]
  • Balansia cyperi[45]
  • Balansia claviceps[45]
  • Balansia epichloë[45]
  • Epichloë amarillans[46]
  • Epichloë cabralii (H)[47]
  • Epichloë canadensis (H)[48][49]
  • Epichloë coenophiala (H)[48][50][51][52]
  • Epichloë festucae[46]
  • Epichloë festucae var. lolii[53][54]
  • Epichloë festucae var. lolii x E. typhina (H)[48][55]
  • Epichloë inebriens[46]
  • Epichloë glyceriae[46]
  • Epichloë mollis[48]
  • Epichloë typhina[45]
  • Epichloë typhina ssp. poae[46][47]
  • Epichloë typhina ssp. clarkii[56]
  • Epichloë sp. AroTG-2(H)[57]
  • Epichloë sp. FaTG-2(H)[48][50][52][58][59]
  • Epichloë sp. FaTG-4(H)[48][52]
  • Hypomyces aurantius[45]
  • Sepedonium sp.[45]
  • Cunnigbamella blakesleana[45]
  • Mucor biemalis[45]
  • Rhizopus nigricans[45]

Psychedelic Effects

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Ergine has only been given a miniscule amount of attention. Albert Hofmann and his colleagues self-administered ergine,[60] and it was adminstered in two clinical trials.[61][14] 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.[13]

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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Albert Hofmann describes ergine as "the main constituent of ololiuhqui".[73] Ololiuhqui was used by South American healers in shamanic healing ceremonies.[74] 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.[75][74]

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.[76]

The Central Intelligence Agency conducted research on the psychedelic properties of Rivea corymbosa seeds for MKULTRA.[77]

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[78]

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:[13][74][79]

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.[80]

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.[81] Another instance is a death due to falling off of a building after ingestion of Hawaiian baby woodrose seeds and alcohol.[82] A study gave mice 3000 mg/kg with no lethal effects.[citation needed]

Adverse Effects

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A 2016 study showed that penniclavine was the predomiant alkaloid in Ipomoea tricolor seeds.[34] Ergoclavines are known to cause convulsive ergotism,[83] the milder form of ergotism. Gangrenous ergotism is caused by ergopeptines: the complex peptide moiety forces persistance at the receptor sites.[84] Ergopeptines are rare in Convolvulaceae, being found in 10 species,[85][86] not including the three that are commonly ingested, although Paulke 2014 says analytical evidence suggests that A. nervosa contains ergopeptines.[87] Many people desire purified seed extracts, but the efficacy of this is questionable, as even pure ergine and ergonovine have shown toxic effects.

Ergine:

"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."

Heim 1968[88]

Ergonovine:

"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,"

Bigwood 1979[89]

Chemical coatings on seeds

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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[90][91] and ergoclavines.[92] Some people even believe that an emetic chemical is purposely added to the seeds to prevent people from ingesting them, but that has never been proven. 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.[93]

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,[94] and Eckart Eich says that they probably don't occur in many Convolvulaceae.[95] There is a similar claim in a publication from 1973, warning about "a strychnine-like alkaloid",[96] but that is probably just a misapplication of the claim that peyote contains strychnine, which, itself, is a rumor.[97]

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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.[98] 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.[99]

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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    The quotes on this page were translated w/ Google Translate.
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    "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." (p. 72)    {{cite book}}: CS1 maint: postscript (link)
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    "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)
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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
  25. ^ 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
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  29. ^ Schultes R (1973). "4. Plants of Hallucinogenic Use / The Fungi". The Botany and Chemistry of Hallucinogens. Springfield, IL: Charles Thomas. p. 37. ISBN 9780398064167.
  30. ^ Wasson RG, Hofmann A, Ruck CA, Webster P (November 25, 2008) [1978]. 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.
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  32. ^ Wasson RG, Hofmann A, Ruck CA, Webster P (November 25, 2008) [1978]. 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.
  33. ^ 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)
  34. ^ 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) (published February 14, 2016): 3093–3102. doi:10.1007/s00216-016-9322-5. PMC 4830885. PMID 26873205
    See 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)
  35. ^ 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.
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  57. ^ 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.
  58. ^ 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.
  59. ^ 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.
  60. ^ Hofmann A (1963). "The Active Principles of the Seeds of Rivea corymbosa and Ipomoea violacea". Harvard Botanical Museum Leaflets. 20 (6). Harvard University Herbaria: 208–210.
    Section: Pharmacological and clinical activity of the isolated alkaloids
    This plant is now considered to be Ipomoea tricolor.
  61. ^ 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.
  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.
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  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): 763–766. 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 (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.
  72. ^ Cole KA. "Ergot Wine Revisited - YouTube". Neurosoup. Archived from the original on 23 July 2021.
  73. ^ Wasson RG, Hofmann A, Ruck CA, Webster P (November 25, 2008) [1978]. 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.
    "This was an experiment performed without attention to 'set and setting' but it proves that ergonovine possesses a psychotropic, mood-changing, slightly hallucinogenic activity when taken in the same amount as [an] effective dose of lysergic acid amide, the main constituent of ololiuhqui." Hofmann, 2. A Challenging Question and My Answer, p. 41
  74. ^ a b c Sewell RA (2008). "Unauthorized research on cluster headache" (PDF). The Entheogen Review. 16 (4): 117–125.
  75. ^ Schultes RE (1941). A Contribution to Our Knowledge of Rivea Corymbosa: The Narcotic Ololinqui of the Aztecs (1st ed.). Botanical Museum of Harvard University.
  76. ^ 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.
  77. ^ "Project Mkultra, Subproject 22 (w/attachments)". Central Intelligence Agency.
  78. ^ Ott J (1996) [1993-07]. "Foreword". Pharmacotheon: Entheogenic Drugs, Their Plant Sources and History (2nd Edition, Densified ed.). Natural Products Co. p. 13. ISBN 9780961423490.
  79. ^ Ingram AL (December 1964). "Morning Glory Seed Reaction". JAMA. 190 (13) (13 ed.): 1133–1134. doi:10.1001/jama.1964.03070260045019. PMID 14212309.
  80. ^ 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.
  81. ^ 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.
  82. ^ 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.
  83. ^ Schardl CL, Panaccione DG, Tudzynski P (2006). "Ergot alkaloids--biology and molecular biology". The Alkaloids. Chemistry and Biology. 63. Elsevier: 45–86. 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)."
    II. Through the Ages: A History of Ergot Alkaloid Use, Abuse, and Poisoning, p. 50    {{cite journal}}: CS1 maint: postscript (link)
  84. ^ 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.
    4.2.5.1 Mechanisms of Action and Therapeutic Relevance, p. 249
  85. ^ 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.
    Containing ergosine: Argyreia luzonensis, A. mollis, A. obtusifolia, A. philippinensis, A. ridleyi, A. splendens
    Ipomoea argyrophylla (ergosine and ergobalansine)
    See "Table 4.1 Unambiguously ergoline-positive Ipomoea species" (pages 225-227) and "Table 4.4 Unambiguously ergoline-positive Argyreia species" (p. 236)
  86. ^ 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
  87. ^ 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)
  88. ^ 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
    3. Results, pages 38-39    {{cite journal}}: CS1 maint: postscript (link)
  89. ^ 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.
  90. ^ Bendz G, Santesson J, eds. (2013-10-14) [1973]. Chemistry in Botanical Classification: Medicine and Natural Sciences: Medicine and Natural Sciences. Elsevier. 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." The Chemistry of Resin Glycosides of the Convolvulaceae Family (H. Wagner), p. 235
  91. ^ 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.
    "Resin glycosides are well known as purgative ingredients," (Abstract)
  92. ^ Schardl CL, Panaccione DG, Tudzynski P (2006). "Ergot alkaloids--biology and molecular biology". The Alkaloids. Chemistry and Biology. 63. Elsevier: 45–86. 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 1 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)."
    II. Through the Ages: A History of Ergot Alkaloid Use, Abuse, and Poisoning, p. 50
  93. ^ 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." (Comment, p. 1134)
    6. Cohen S (April 1964). "Suicide Following Morning Glory Seed Ingestion". The American Journal of Psychiatry. 120 (10): 1024–1025. doi:10.1176/ajp.120.10.1024. PMID 14138842.
    8. Frear DE (1963). Pesticide Handbook. State College, Pa: College Science Publishers. p. 8.
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    See 6.2 Cyanogenic Glycosides, p. 274
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    "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." (OLOLUIQUE and related sacraments in the Morning Glory (Bindweed) family, p. 13)
  97. ^ 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." (Peyote: Lophophora williamsii)
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