Editing Ergoline (section)

==Natural occurrence==
Ergoline alkaloids are found in [[fungi]] such as Claviceps purpurea, Claviceps paspali,<ref name=":0">{{Cite book | vauthors = Schultes R |title=The Botany and Chemistry of Hallucinogens |publisher=Charles Thomas |year=1973 |isbn=9780398064167 |location=Springfield, IL |language=En | chapter = 4. Plants of Hallucinogenic Use / The Fungi | page =  37
|quote = <br>“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.” 4. Plants of Hallucinogenic Use / The Fungi, p. 37
}}</ref><ref>{{Cite book | vauthors = Wasson RG, Hofmann A, Ruck CA, Webster P |url=https://books.google.com/books?id=7JC7EAAAQBAJ&pg=PA42 |title=The Road to Eleusis: Unveiling the Secret of the Mysteries |publisher=North Atlantic Books |isbn=978-1-55643-752-6 | veditors = Forte R |edition=30th Anniversary |location=Berkeley, Calif. |publication-date=November 25, 2008 |orig-date=1978 |language=En
|quote = <br>“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.” Albert Hofmann, 2. A Challenging Question and my Answer, p. 42
}}</ref> and the related Periglandula, which have a permanent, symbiotic bond with numerous flowering vines, most notably, ''[[Turbina corymbosa]]'' and ''[[Ipomoea tricolor]]'' (“morning glory”).<ref>{{cite book | vauthors = Leistner E, Steiner U | chapter = The Genus Periglandula and Its Symbiotum with Morning Glory Plants (Convolvulaceae) |publication-date=February 3, 2018 | veditors = Anke T, Schüffler A | title = Physiology and Genetics |pages=131–147 |chapter-url= http://link.springer.com/10.1007/978-3-319-71740-1_5 |access-date=2024-11-21 |place=Cham |publisher=Springer International Publishing |language=en |doi=10.1007/978-3-319-71740-1_5 |isbn=978-3-319-71739-5 }}</ref> Ergolines are concentrated in the seeds,<ref>{{cite journal | vauthors = Nowak J, Woźniakiewicz M, Klepacki P, Sowa A, Kościelniak P | title = Identification and determination of ergot alkaloids in Morning Glory cultivars | journal = Analytical and Bioanalytical Chemistry | volume = 408 | issue = 12 | pages = 3093–3102 | date = May 2016 | pmid = 26873205 | pmc = 4830885 | doi = 10.1007/s00216-016-9322-5 | quote =  <br>“ergine and ergometrine concentration is 12-fold lower in plant samples than in seeds.” Analysis of IP-HB2 young plants }}</ref> which have been used for ages by indigenous central/south Americans<ref>{{Cite book | vauthors = Ruck CA |title=Sacred Mushrooms of the Goddess: The Secrets of Eleusis |date=2006 |publisher=Ronin Publishing, Inc |isbn=978-1-57951-030-5 |location=Berkeley, California | quote = <br>“Ololiuhqui was far more prominent as an entheogen here in Mesoamerica than those mushrooms; the mushrooms are mentioned only here and there by a few competent chroniclers; yet almost an entire book was devoted to denouncing mainly the ololiuhqui idolatry. The annals of the Inquisition contain many times more autos de fe for ololiuhqui than for mushrooms.” Jonathan Ott, quoted in 15. Mixing the Kykeon Anew (section: Ergine)}}</ref> (i.e. T. corymbosa seeds are known as ''ololiuhqui''<ref name="Schardl20063">{{cite book|vauthors=Schardl CL, Panaccione DG, Tudzynski P|year=2006|title=Ergot alkaloids&nbsp;– biology and molecular biology|journal=The Alkaloids. Chemistry and Biology |series=The Alkaloids: Chemistry and Biology|volume=63|pages=45–86|doi=10.1016/S1099-4831(06)63002-2|isbn=978-0-12-469563-4|pmid=17133714}}</ref><ref>{{cite journal | vauthors = Carod-Artal FJ | title = Hallucinogenic drugs in pre-Columbian Mesoamerican cultures | journal = Neurologia | volume = 30 | issue = 1 | pages = 42–49 | year = 2015 | pmid = 21893367 | doi = 10.1016/j.nrl.2011.07.003 | doi-access = free }}</ref>) The principal alkaloids in the seeds appear to be [[ergine]] and [[isoergine]], but they're just decomposition products of [[lysergic acid hydroxyethylamide]], isolysergic hydroxyethylamide, [[ergonovine|lysergic acid hydroxymethylethylamide (syn. ''ergonovine'')]], and isolysergic acid hydroxymethylethylamide (syn. ''ergonovinine'').<ref>{{Cite book | vauthors = Shulgin A |chapter-url=https://books.google.com/books?id=yt2KcKcJROgC&pg=PA71 |title=Psychopharmacological agents |publisher=Academic Press |publication-date=2012-12-02 |orig-date=1976 |isbn=978-0-12-290559-9 | veditors = Maxwell G |series=Medicinal Chemistry |volume=4 |location=New York |pages=71–72 |chapter=4. Psychotomimetic Agents |quote = <br>“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)}}</ref><ref>{{Cite book | vauthors = Schultes RE, Hofmann A |title=The Botany and Chemistry of Hallucinogens  |publisher=Charles Thomas |year=1973 |isbn=9780398064167 |location=Springfield, IL |pages=246 |quote = <br>“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}}</ref><ref>{{Cite journal | vauthors = Flieger M, Sedmera P, Vokoun J, ((R̆ic̄icovā A)), ((R̆ehác̆ek Z)) |publication-date=1982-02-19 |title=Separation of four isomers of lysergic acid α-hydroxyethylamide by liquid chromatography and their spectroscopic identification |url=https://linkinghub.elsevier.com/retrieve/pii/S0021967300848955 |journal=Journal of Chromatography A |volume=236 |issue=2 |pages=441–452 |doi=10.1016/S0021-9673(00)84895-5 |issn=0021-9673|url-access=subscription }}</ref><ref>{{Cite journal | vauthors = Ramstad E |publication-date=1968 |title=Chemistry of alkaloid formation in ergot |journal=Lloydia |volume=31 |pages=327–341}}</ref><ref>{{cite journal | vauthors = Kleinerová E, Kybal J | title = Ergot alkaloids. IV. Contribution to the biosynthesis of lysergic acid amides | journal = Folia Microbiologica | volume = 18 | issue = 5 | pages = 390–392 | pmid = 4757982 | doi = 10.1007/BF02875934 | publication-date = September 1973 }}</ref><ref>{{cite journal | vauthors = Panaccione DG, Tapper BA, Lane GA, Davies E, Fraser K | title = Biochemical outcome of blocking the ergot alkaloid pathway of a grass endophyte | journal = Journal of Agricultural and Food Chemistry | volume = 51 | issue = 22 | pages = 6429–6437 | date = October 2003 | pmid = 14558758 | doi = 10.1021/jf0346859 | bibcode = 2003JAFC...51.6429P }}</ref><ref>{{cite book | vauthors = Panaccione DG | chapter = Ergot alkaloids | title = The Mycota, Industrial Applications | edition = 2nd | veditors = Hofrichter M | publisher = Springer-Verlag | location = Berlin-Heidelberg, Germany | date = 2010 | volume = 10 | pages = 195–214 }}</ref> All of the other ergolines have been quantified in very small amts. except for penniclavine, which was found to be the predominant ergoline in a 2016 assay of I. tricolor seeds.<ref name=nowak>{{cite journal | vauthors = Nowak J, Woźniakiewicz M, Klepacki P, Sowa A, Kościelniak P | title = Identification and determination of ergot alkaloids in Morning Glory cultivars | journal = Analytical and Bioanalytical Chemistry | volume = 408 | issue = 12 | pages = 3093–3102 | date = May 2016 | pmid = 26873205 | pmc = 4830885 | doi = 10.1007/s00216-016-9322-5 | quote =  <br>See Table 3 under “Analysis of different Ipomoea seeds”.<br>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. | publication-date = February 14, 2016 }}</ref> Ergolines have been identified in 42 Morning Glory species.<ref>{{Cite book | vauthors = Eich E |url=https://link.springer.com/book/10.1007/978-3-540-74541-9 |title=Solanaceae and convolvulaceae - secondary metabolites: biosynthesis, chemotaxonomy, biological and economic significance: a handbook |publisher=Springer-Verlag |isbn=978-3-540-74540-2 |location=Berlin, Heidelberg |publication-date=January 12, 2008 |language=En |chapter=4.2 Ergolines |doi=10.1007/978-3-540-74541-9 |oclc=195613136}}<br>Table 4.1 Unambiguously ergoline-positive Ipomoea species (pages 225-227)<br>Table 4.4 Unambiguously ergoline-positive Argyreia species (p. 236)<br>Table 4.5 Unambiguously ergoline-positive Stictocardia and Turbina species (p. 238)
</ref> The only ergolines of these seeds that have been trialed as isolates are [[ergine]], [[ergonovine]], and lysergol, with lysergol showing the weakest effect<ref>{{cite journal | vauthors = Heim E, Heimann H, Lukács G | title = Die psychische Wirkung der mexikanischen Droge "Ololiuqui" am Menschen | language = de | journal = Psychopharmacologia | volume = 13 | issue = 1 | pages = 35–48 | date = 1968 | pmid = 5675457 | doi = 10.1007/BF00401617 | postscript = <br>c) ᴅ-Lysergol<br><br>“Changes occurred only with a dosage of 8 mg, with a noticeable slowing of expression and behavior. The facial expression appeared flat, and speech showed a reduction in the five expressive qualities. Subjectively, fewer vegetative sensations were observed, but there was a marked inhibition of initiative.” 3. Results, p. 40<br>Translated from German with ChatGPT.}}</ref> (refs: [[Ergine#Psychedelic Effects|Ergine / Psychedelic Effects]], [[Ergometrine#Psychedelic Effects|Ergometrine / Psychedelic Effects]]).