Editing Psychedelic drug (section)

====Tryptamine and lysergamide psychedelics====
[[Austrian people|Austrian]] anthropologist and [[ethnobotanist]] Blas Pablo Reko, traveling through [[Central America|Central]] and [[South America]], wrote of the use of teonanacatl by native Mexican people in [[Oaxaca]] in 1919.<ref name="McKenna1999" /> Reko subsequently sent samples of teonanacatl (''Psilocybe mexicana'') as well as ''[[Ipomoea violacea]]'' (morning glory) seeds to [[Swedish people|Swedish]] anthropologist [[Henry Wassén]] in 1937.<ref name="McKenna1999" /> Reko had obtained the mushroom sample from Austrian [[engineer]] [[Robert J. Weitlaner|Robert Weitlaner]] who was working in [[Mexico]].<ref name="McKenna1999" /> Eventually, Wassén forwarded Reko and Weitlaner's mushroom sample to [[Harvard University]], where the mushrooms came to the attention of American ethnobotanist [[Richard Evans Schultes]].<ref name="McKenna1999" /><ref name="Nichols2020" /> However, they had decomposed so badly that they could not be identified.<ref name="McKenna1999" /><ref name="Nichols2020" /> Prior to Wassén obtaining specimens around 1936, the existence of teonanacatl was very controversial and was debated and even denied by some.<ref name="Nichols2020" /> In 1938, a small group of Westerners, which included Weitlaner's daughter and American anthropologist [[Jean Basset Johnson]], attended a mushroom ceremony.<ref name="McKenna1999" /><ref name="Nichols2020" /> They were the first Westerners known to do so and described the event.<ref name="McKenna1999" /><ref name="Nichols2020" /> Schultes published reviews of teonanacatl being a hallucinogenic mushroom in the late 1930s.<ref name="McKenna1999" /><ref name="Schultes1939">Schultes, R. E. (1939). The identifications of teonanácatl, a narcotic basidiomycete of the Aztecs. ''Botanical Museum Leaflets'', Harvard University, 7, 37–55.</ref> Schultes obtained specimens of three of the hallucinogenic mushrooms used in ceremonies, including ''[[Psilocybe caerulescens]]'', ''[[Panaeolus campanulatus]]'', and ''[[Stropharia cubensis]]'', but further investigations of the mushrooms were interrupted by [[World War II]].<ref name="Nichols2020" />

[[Ergine]] (lysergic acid amide; LSA) and [[isoergine]] (isolysergic acid amide; iso-LSA) were first identified from [[hydrolysis]] of [[ergot alkaloid]]s in 1932 and 1936, respectively.<ref name="BrimblecombePinder1975">{{cite book | vauthors = Brimblecombe RW, Pinder RM | chapter = Indolealkylamines and Related Compounds | pages = 98–144 | title = Hallucinogenic Agents | date = 1975 | publisher = Wright-Scientechnica | location = Bristol | isbn = 978-0-85608-011-1 | oclc = 2176880 | ol = OL4850660M | url = https://bitnest.netfirms.com/external/Books/978-0-85608-011-1}}</ref><ref name="SmithTimmis1932">{{cite journal | vauthors = Smith S, Timmis GM |date=1932 |title=98. The alkaloids of ergot. Part III. Ergine, a new base obtained by the degradation of ergotoxine and ergotinine |url=https://xlink.rsc.org/?DOI=jr9320000763 |journal=Journal of the Chemical Society (Resumed) |language=en |pages=763–766 |doi=10.1039/jr9320000763 |issn=0368-1769}}</ref><ref name="SmithTimmis1936">{{cite journal | vauthors = Smith S, Timmis GM | title=311. The alkaloids of ergot. Part VII. isoErgine and isolysergic acids | journal=Journal of the Chemical Society (Resumed) | date=1936 | issn=0368-1769 | doi=10.1039/jr9360001440 | page=1440}}</ref> In 1938, [[Swiss people|Swiss]] chemist [[Albert Hofmann]], working at [[Sandoz Laboratories]], [[chemical synthesis|synthesized]] [[lysergic acid diethylamide]] (LSD), a [[synthetic compound|synthetic]] [[chemical derivative|derivative]] of ergine, while developing new [[oxytocic]] [[drug]]s derived from [[ergot]].<ref name="McKenna1999" /> LSD was not further investigated and was placed in storage for 5{{nbsp}}years.<ref name="McKenna1999" /> In 1943 however, Hofmann worked with LSD again and accidentally discovered its hallucinogenic effects when minute amounts of the potent psychedelic absorbed through his skin.<ref name="McKenna1999" /><ref name="WalkerPullellaPiggott2023" /> His subsequent [[self-experiment]] with LSD three days later on April 19 is the psychedelic holiday [[Bicycle Day (psychedelic holiday)|Bicycle Day]].<ref name="BelouinHenningfield2018">{{cite journal | vauthors = Belouin SJ, Henningfield JE | title = Psychedelics: Where we are now, why we got here, what we must do | journal = Neuropharmacology | volume = 142 | issue = | pages = 7–19 | date = November 2018 | pmid = 29476779 | doi = 10.1016/j.neuropharm.2018.02.018 | url = | doi-access = free }}</ref> Hofmann and his colleague, [[psychiatrist]] [[Werner Stoll]], first described LSD in 1943 and first described its psychedelic effects in 1947.<ref name="McKenna1999" /><ref name="Gach2008">{{cite book | vauthors = Gach J | title=History of Psychiatry and Medical Psychology | chapter=Biological Psychiatry in the Nineteenth and Twentieth Centuries | publisher=Springer US | publication-place=Boston, MA | date=2008 | isbn=978-0-387-34707-3 | doi=10.1007/978-0-387-34708-0_12 | pages=381–418 | url=https://www.timothydavidson.com/Library/Books/Wallace-2008-History%20of%20Psychiatry%20and%20Medical%20Psychology/Wallace%20and%20Gach-2008-History%20of%20Psychiatry%20and%20Medical%20Psychology.pdf#page=413 | archive-url=https://web.archive.org/web/20250319140308/https://www.timothydavidson.com/Library/Books/Wallace-2008-History%20of%20Psychiatry%20and%20Medical%20Psychology/Wallace%20and%20Gach-2008-History%20of%20Psychiatry%20and%20Medical%20Psychology.pdf#page=413 | archive-date=19 March 2025 | quote=In 1938 the Swiss chemist Albert Hofmann produced lysergic acid diethylamide (LSD)—the first, and most prominent, of these chemically synthesized agents—in the course of a systematic investigation of partially synthetic amides of lysergic acid in the Sandoz Pharmaceutical Laboratories in Basel (Hofmann 1970). [Taking] LSD by accident in 1943, Hofmann discovered its psychoactivity. He then experimented with it on himself and found that it produced a peculiar restlessness, extreme activity of the imagination, and an uninterrupted stream of images. Hofmann did not publish the results of his experiment, though he became quite famous later. Hofmann and Arthur Stoll, the head of the Sandoz pharmaceutical laboratory in Basle, published the first paper on the synthesis of LSD in 1943, while Stoll went on to publish the first paper on the effects of lysergic diethylamide acid in 1947. [...] Stoll, Arthur and Hofmann, Albert. 1943. Partialsynthese von Alkaloiden vom Typus des Ergobasins. Helv. Chim. Acta 26:944. Stoll, Arthur. 1947. Lysergsäure-diäthylamid, ein Phantastikum aus der Mutterkorngruppe. Schweiz. Arch. Neurol. Psychiat. 60:279. [The first paper on the hallucinogenic effect of LSD.]}}</ref><ref name="StollHofmann1943">{{cite journal | vauthors = Stoll A, Hofmann A | title=Partialsynthese von Alkaloiden vom Typus des Ergobasins. (6. Mitteilung über Mutterkornalkaloide) | trans-title=Partial synthesis of ergobasine-type alkaloids. (6th report on ergot alkaloids) | journal=Helvetica Chimica Acta | volume=26 | issue=3 | date=3 May 1943 | issn=0018-019X | doi=10.1002/hlca.19430260326 | pages=944–965}}</ref><ref name="Stoll1947">{{cite journal | vauthors = Stoll WA | title = 11. Lysergsäure-diäthylamid, ein Phantastikum aus der Mutterkorngruppe | trans-title = 11. Lysergic Acid Diethylamide, a Hallucinogen From the Ergot Group | journal = Schweizer Archiv für Neurologie und Psychiatrie | volume = 60 | issue = | date = 1947 | pages = 279–323 | issn = 0258-7661 | url = https://bibliography.maps.org/resources/download/16963| archive-url = https://web.archive.org/web/20250401005831/https://bibliography.maps.org/resources/download/16963 | archive-date = 1 April 2025 }}</ref><ref name="Stoll1949">{{cite journal | vauthors = Stoll W | title = Ein neues, in sehr kleinen Mengen wirksames Phantastikum | trans-title = A New Phantasticum, Effective in Very Tiny Amounts | journal = Schweizer Archiv für Neurologie und Psychiatrie | volume = 64 | issue = | pages = 483–484 | date = 1949 | issn = 0258-7661 | url = https://bibliography.maps.org/resources/download/16676| archive-url = https://web.archive.org/web/20250401012040/https://bibliography.maps.org/resources/download/16676 | archive-date = 1 April 2025 }}</ref> LSD began being distributed by Sandoz Laboratories for research purposes under the brand name Delysid in 1949.<ref name="Nichols2018b">{{cite journal | vauthors = Nichols DE | title = Dark Classics in Chemical Neuroscience: Lysergic Acid Diethylamide (LSD) | journal = ACS Chem Neurosci | volume = 9 | issue = 10 | pages = 2331–2343 | date = October 2018 | pmid = 29461039 | doi = 10.1021/acschemneuro.8b00043 | url = }}</ref><ref name="Bonson2018">{{cite journal | vauthors = Bonson KR | title = Regulation of human research with LSD in the United States (1949-1987) | journal = Psychopharmacology (Berl) | volume = 235 | issue = 2 | pages = 591–604 | date = February 2018 | pmid = 29147729 | doi = 10.1007/s00213-017-4777-4 | url = }}</ref>

Schultes described the indigenous and shamanic use of [[dimethyltryptamine]] (DMT)-containing psychedelic plants in 1954 and also described the use of hallucinogenic [[morning glories]] in the 1950s.<ref name="McKenna1999" /> The psychedelic effects of synthesized DMT were described by [[Hungarian people|Hungarian]] chemist and psychiatrist [[Stephen Szára]] in 1956.<ref name="Garcia-RomeuKersgaardAddy2016" /><ref name="Szára2007">{{cite journal | vauthors = Szára S | title = DMT at fifty | journal = Neuropsychopharmacol Hung | volume = 9 | issue = 4 | pages = 201–205 | date = December 2007 | pmid = 18510265 | doi = | url = }}</ref><ref name="McKenna1999" /><ref name="Szara1956">{{cite journal | vauthors = Szara S | title = Dimethyltryptamin: its metabolism in man; the relation to its psychotic effect to the serotonin metabolism | journal = Experientia | volume = 12 | issue = 11 | pages = 441–442 | date = November 1956 | pmid = 13384414 | doi = 10.1007/BF02157378 | url = }}</ref><ref name="SzaraSai-HalaszBoszormenyi1958">{{cite journal | vauthors = Szara I, Sai-Halasz A, Boszormenyi Z | title = Dimethyltryptamine als neues Psychotikum | trans-title = Dimethyltryptamine as a new psychotic agent | language = German | journal = Acta Physiol Acad Sci Hung | volume = 11 | issue = Suppl | pages = 78–79 | date = 1958 | pmid = 13469470 | doi = | url = }}</ref> Osmond described the hallucinogenic and other effects of morning glory seeds in clinical studies in 1955.<ref name="BrimblecombePinder1975" /> Hofmann identified and described ergine and isoergine as the active constituents of morning glory seeds in 1960.<ref name="WalkerPullellaPiggott2023" /><ref name="HofferOsmond1967">{{cite book | author1=[[Abram Hoffer]] | author2=[[Humphrey Osmond]] | chapter=Chapter II A d-Lysergic Acid Diethylamide | pages=83–236 | chapter-url=https://bitnest.netfirms.com/external/Books/TheHallucinogens#page=91 | title=The Hallucinogens | publisher=Elsevier | date=1967 | isbn=978-1-4832-3296-6 | doi=10.1016/B978-1-4832-3296-6.50005-7 | lccn=66030086 | oclc=332437 | ol=OL35255701M  | url=https://bitnest.netfirms.com/external/Books/TheHallucinogens}}</ref><ref name="Hofmann1963" /><ref name="HofmannTscherter1960">{{cite journal | vauthors = Hofmann A, Tscherter H | title=Isolierung von Lysergsäure-Alkaloiden aus der mexikanischen Zauberdroge Ololiuqui (Rivea corymbosa (L.) Hall. f.) | trans-title=Isolation of lysergic acid alkaloids from the Mexican magic drug Ololiuqui (Rivea corymbosa (L.) Hall. f.) | journal=Experientia | volume=16 | issue=9 | date=1960 | issn=0014-4754 | doi=10.1007/BF02178840 | doi-access=free | pages=414 | pmid=13715089 | url=https://link.springer.com/content/pdf/10.1007/BF02178840.pdf | language=de | access-date=28 March 2025}}</ref> Their hallucinogenic effects were first described by Hofmann in 1963.<ref name="BrimblecombePinder1975" /><ref name="Hofmann1963">{{cite journal | vauthors = Hofmann A | title=The Active Principles of the Seeds of Rivea Corymbosa and Ipomoea Violacea | journal=Botanical Museum Leaflets, Harvard University | publisher=Harvard University Herbaria | volume=20 | issue=6 | year=1963 | issn=0006-8098 | jstor=41762231 | pages=194–212 | doi=10.5962/p.168542 | url=http://www.jstor.org/stable/41762231 | archive-url=https://web.archive.org/web/20250328174012/https://bibliography.maps.org/resources/download/13684 | archive-date = 28 March 2025}}</ref>

In 1952, couple and amateur [[ethnomycologist]]s [[R. Gordon Wasson]] and [[Valentina Wasson]] learned of the ritual use of hallucinogenic mushrooms in the 16th century in Mexico from the published work of Schultes.<ref name="Nichols2020" /><ref name="Mangini2024">{{cite journal | last=Mangini | first=Mariavittoria | title=Unseen Women in Psychedelic History | journal=Journal of Humanistic Psychology | volume=64 | issue=4 | date=2024 | issn=0022-1678 | doi=10.1177/00221678211029186 | pages=635–652}}</ref> They made several trips to Mexico in search of the mushrooms.<ref name="Nichols2020" /><ref name="Mangini2024" /> In mid-1955, the Wassons participated in a mushroom ceremony with [[Mazatec people|Mazatec]] [[curandera]] [[Maria Sabina]] in [[Huautla de Jiménez]], Oaxaca, Mexico.<ref name="Nichols2020" /><ref name="Mangini2024" /> Gordon Wasson published his experience in an article for ''[[Life Magazine|Life]]'' magazine titled "[[Seeking the Magic Mushroom]]" in 1957, while Valentina Wasson published her experience as "I Ate the Sacred Mushroom" in ''[[This Week (magazine)|This Week]]'' magazine the same year.<ref name="Nichols2020" /><ref name="Mangini2024" /> Later in 1957, a second expedition was made by the Wassons to Mexico with [[French people|French]] mycologist [[Roger Heim]].<ref name="Nichols2020" /> Heim identified several of the mushrooms as belonging to the [[genus]] ''[[Psilocybe]]''.<ref name="Nichols2020" /> They collected samples of the mushrooms and Heim sent a sample to Hofmann.<ref name="Nichols2020" /> Hofmann identified psilocybin as the active constituent in 1958 and developed a [[chemical synthesis]] for it.<ref name="Nichols2020" /><ref name="Garcia-RomeuKersgaardAddy2016" /><ref name="McKenna1999" /> Sandoz Pharmaceuticals began distributing [[tablet (pharmacy)|tablet]]s of psilocybin under the brand name Indocybin in 1960.<ref name="Nichols2020" />

French scientists [[Césaire Phisalix]] and Gabriel Bertrand isolated [[bufotenin]] from ''[[Bufo]]'' toads in 1893 and named it.<ref name="LyttleGoldsteinGartz1996">{{cite journal | vauthors = Lyttle T, Goldstein D, Gartz J | title = Bufo toads and bufotenine: fact and fiction surrounding an alleged psychedelic | journal = J Psychoactive Drugs | volume = 28 | issue = 3 | pages = 267–290 | date = 1996 | pmid = 8895112 | doi = 10.1080/02791072.1996.10472488 | url = }}</ref><ref name="BochnerGoyffon2007">Bochner, R., & Goyffon, M. (2007). L’œuvre scientifique de Césaire Phisalix (1852-1906), découvreur du sérum antivenimeux. Bull Soc Herp Fr, 123, 15-46. https://www.icict.fiocruz.br/sites/www.icict.fiocruz.br/files/L%20oeuvre%20scientifique%20de%20Cesaire%20Phisalix%20(1852--1906)%20decouvreur%20du%20serum%20antivenimeux.pdf</ref><ref name="PhisalixBertrand1893">Phisalix C, Bertrand G (1893) Toxicité comparée du sang et du venin de crapaud commun, considérée au point de vue de la sécrétion interne des glandes cutanées de cet animal. C R Soc Biol 45:477–479. https://scholar.google.com/scholar?cluster=14905926340091797397</ref> The compound was first isolated to purity by Austrian chemist Hans Handovsky in 1920.<ref name="LyttleGoldsteinGartz1996" /> Clinical studies assessed the effects of bufotenin and were published starting in 1956.<ref name="LyttleGoldsteinGartz1996" /><ref name="McBride2000" /><ref name="ShenJiangWinter2010" /> However, the findings of these studies were conflicting, and bufotenin developed a long-standing reputation of being inactive and toxic.<ref name="LyttleGoldsteinGartz1996" /><ref name="McBride2000">{{cite journal | vauthors = McBride MC | title = Bufotenine: toward an understanding of possible psychoactive mechanisms | journal = Journal of Psychoactive Drugs | volume = 32 | issue = 3 | pages = 321–331 | date = 2000 | pmid = 11061684 | doi = 10.1080/02791072.2000.10400456 }}</ref><ref name="ShenJiangWinter2010"/> American ethnobotanist [[Jonathan Ott]] and colleagues subsequently showed in 2001 that bufotenin is in fact a psychedelic and does not necessarily produce major adverse effects, although marked [[nausea]] and [[vomiting]] are prominent.<ref name="ShenJiangWinter2010" /><ref name="Ott2001b">{{cite book | vauthors = [[Jonathan Ott|Ott J]] | chapter=Shamanic-Snuff Psychonautica: Pharmañopo: Bufotenine—Psychonautics | pages=99–116 (105–112, 114–115) | title=Shamanic Snuffs or Entheogenic Errhines | publisher=Entheobotanica | year=2001 | isbn=978-1-888755-02-2 | oclc=56061312 | url=https://books.google.com/books?id=AUP7NwAACAAJ | chapter-url=https://archive.org/details/vdocuments.mx_unknown-55b347d139b58/page/n51/mode/1up | access-date=24 January 2025 }}</ref><ref name="Ott2001a">{{cite journal | vauthors = [[Jonathan Ott|Ott J]] | title = Pharmañopo-psychonautics: human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine | journal = Journal of Psychoactive Drugs | volume = 33 | issue = 3 | pages = 273–281 | year = 2001 | pmid = 11718320 | doi = 10.1080/02791072.2001.10400574 | s2cid = 5877023 }}</ref> The related psychedelic [[5-MeO-DMT]] was first synthesized by [[Japanese people|Japanese]] chemists Toshio Hoshino and Kenya Shimodaira in 1935.<ref name="Delgrasso2024" /><ref name="ErmakovaDunbarRucker2022">{{cite journal | vauthors = Ermakova AO, Dunbar F, Rucker J, Johnson MW | title = A narrative synthesis of research with 5-MeO-DMT | journal = J Psychopharmacol | volume = 36 | issue = 3 | pages = 273–294 | date = March 2022 | pmid = 34666554 | pmc = 8902691 | doi = 10.1177/02698811211050543 | url = }}</ref> It was later isolated from ''[[Dictyoloma incanescens]]'' in 1959.<ref name="ErmakovaDunbarRucker2022" /> Subsequently, 5-MeO-DMT was isolated from numerous other plants and fungi.<ref name="ErmakovaDunbarRucker2022" /><ref name="Delgrasso2024" /> The compound was isolated from the skin of toads, specifically the [[Colorado River toad]] (''Incilius alvarius'', formerly ''Bufo alvarius''), by [[Italian people|Italian]] chemist and pharmacologist [[Vittorio Erspamer]] in 1967.<ref name="Delgrasso2024">{{cite journal | last=Delgrasso | first=Azul | title=Defining 5-MeO-DMT in Historical and Cultural Contexts | journal=World Futures | volume=80 | issue=2 | date=17 February 2024 | issn=0260-4027 | doi=10.1080/02604027.2024.2330255 | pages=174–197}}</ref><ref name="ErmakovaDunbarRucker2022" /><ref name="ErspamerVitaliRoseghini1967">{{cite journal | vauthors = Erspamer V, Vitali T, Roseghini M, Cei JM | title = 5-Methoxy- and 5-hydroxyindoles in the skin of Bufo alvarius | journal = Biochem Pharmacol | volume = 16 | issue = 7 | pages = 1149–1164 | date = July 1967 | pmid = 6053590 | doi = 10.1016/0006-2952(67)90147-5 | url = http://sedici.unlp.edu.ar/handle/10915/88423}}</ref> A 1984 pamphlet by Albert Most (real name Ken Nelson), titled ''[[Bufo Alvarius: the Psychedelic Toad of the Sonoran Desert]]'', described how to obtain and use Colorado River toad secretions as a psychedelic drug, and this started its recreational use.<ref name="Siebert2021">{{cite web | last=Siebert | first=Amanda | title=Hamilton Morris On Mistakes, 5-MeO-DMT And Preserving Psychedelic Toads | website=Forbes | date=8 January 2021 | url=https://www.forbes.com/sites/amandasiebert/2021/01/08/hamilton-morris-on-mistakes-5-meo-dmt-and-preserving-psychedelic-toads/ | access-date=4 April 2025}}</ref><ref name="WeilDavis1994">{{cite journal | vauthors = Weil AT, Davis W | title = Bufo alvarius: a potent hallucinogen of animal origin | journal = J Ethnopharmacol | volume = 41 | issue = 1–2 | pages = 1–8 | date = January 1994 | pmid = 8170151 | doi = 10.1016/0378-8741(94)90051-5 | url = }}</ref><ref name="ErmakovaDunbarRucker2022" />