Editing Dimethyltryptamine (section)

==History==
{{See also|Ayahuasca#History}}

DMT derived from [[plant]]-based sources has been used as an [[entheogen]] in [[South America]] for thousands of years.<ref name="MillerAlbarracin-JordanMoore2019">{{cite journal | vauthors = Miller MJ, Albarracin-Jordan J, Moore C, Capriles JM | title = Chemical evidence for the use of multiple psychotropic plants in a 1,000-year-old ritual bundle from South America | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 116 | issue = 23 | pages = 11207–11212 | date = June 2019 | pmid = 31061128 | pmc = 6561276 | doi = 10.1073/pnas.1902174116 | bibcode = 2019PNAS..11611207M | doi-access = free }}</ref><ref name="Anwar2019">{{Cite web|url=https://news.berkeley.edu/2019/05/06/ayahuasca-sacred-bundle/|title=Ayahuasca fixings found in 1,000-year-old Andean sacred bundle|vauthors=Anwar Y|date=6 May 2019|website=Berkeley News|language=en-US|access-date=21 May 2019|archive-date=12 May 2019|archive-url=https://web.archive.org/web/20190512172214/https://news.berkeley.edu/2019/05/06/ayahuasca-sacred-bundle/|url-status=live}}</ref>

DMT was first synthesized in 1931 by Canadian chemist Richard Helmuth Fredrick Manske.<ref name="Shulgin1976">{{cite journal | vauthors = Shulgin AT | title=Profiles of Psychedelic Drugs: DMT & TMA-2 | journal=Journal of Psychedelic Drugs | volume=8 | issue=2 | date=1976 | issn=0022-393X | doi=10.1080/02791072.1976.10471846 | pages=167–169 | url=https://www.tandfonline.com/doi/full/10.1080/02791072.1976.10471846 | access-date=8 April 2025| url-access=subscription }}</ref><ref name="Manske R.H.F. 1931 592–600">{{cite journal|year=1931|title=A synthesis of the methyltryptamines and some derivatives|url=http://rparticle.web-p.cisti.nrc.ca/rparticle/AbstractTemplateServlet?calyLang=eng&journal=cjr&volume=5&year=&issue=5&msno=cjr31-097|journal=Canadian Journal of Research|volume=5|issue=5|pages=592–600|doi=10.1139/cjr31-097| vauthors = Manske RH |bibcode=1931CJRes...5..592M|url-access=subscription}}{{Dead link|date=July 2018 |bot=InternetArchiveBot |fix-attempted=yes }}</ref><ref name="bdmxab">{{cite journal|date=November 1977|title=DMT: the fifteen minute trip|url=http://jeremybigwood.net/JBsPUBS/DMT/|journal=Head|volume=2|issue=4|pages=56–61| vauthors = Bigwood J, Ott J |access-date=28 November 2010|archive-url=https://web.archive.org/web/20060127003553/http://jeremybigwood.net/JBsPUBS/DMT/|archive-date=27 January 2006}}</ref> In general, its discovery as a natural product is credited to Brazilian chemist and [[microbiologist]] Oswaldo Gonçalves de Lima, who isolated an alkaloid he named ''nigerina'' (nigerine) from the root bark of ''[[Mimosa tenuiflora]]'' in 1946.<ref name="bdmxab" /><ref name="strassman" /><ref name="ott1996">{{cite book |title=Pharmacotheon: Entheogenic Drugs, Their Plant Sources and History | vauthors = Ott J |author-link=Jonathan Ott |edition=2nd, densified |year=1996 |publisher=Natural Products |location=Kennewick, WA |isbn=978-0-9614234-9-0}}</ref> However, in a careful review of the case [[Jonathan Ott]] shows that the [[empirical formula]] for nigerine determined by Gonçalves de Lima, which notably contains an atom of oxygen, can match only a partial, "impure" or "contaminated" form of DMT.<ref name="ott1998">{{cite book |vauthors=Ott J |author-link1=Jonathan Ott |veditors=Müller-Ebeling C |title=Special: Psychoactivity |series=Yearbook for Ethnomedicine and the Study of Consciousness |volume=6/7 (1997/1998) |year=1998 |publisher=VWB |location=Berlin |isbn=978-3-86135-033-0 |chapter=Pharmahuasca, anahuasca and vinho da jurema: human pharmacology of oral DMT plus harmine |chapter-url=https://www.erowid.org/references/texts/show/7105docid6446 |access-date=2010-11-29 |archive-date=2018-10-31 |archive-url=https://web.archive.org/web/20181031212537/https://www.erowid.org/references/texts/show/7105docid6446 |url-status=live }}</ref> It was only in 1959, when Gonçalves de Lima provided American chemists a sample of ''Mimosa tenuiflora'' roots, that DMT was unequivocally identified in this plant material.<ref name="ott1998" /><ref>{{cite journal| vauthors = Pachter IJ, Zacharias DE, Ribeiro O |title=Indole alkaloids of ''Acer saccharinum'' (the silver maple), ''Dictyoloma incanescens'', ''Piptadenia colubrina'', and ''Mimosa hostilis'' |journal=Journal of Organic Chemistry |date=September 1959 |volume=24 |issue=9 |pages=1285–1287 |doi=10.1021/jo01091a032}}</ref> Less ambiguous is the case of isolation and formal identification of DMT in 1955 in seeds and pods of ''[[Anadenanthera peregrina]]'' by a team of American chemists led by Evan Horning (1916–1993).<ref name="ott1998" /><ref>{{cite journal | vauthors = Fish MS, Johnson NM, Horning EC |date=November 1955 |title=Piptadenia alkaloids. Indole bases of ''P. peregrina'' (L.) Benth. and related species |journal=Journal of the American Chemical Society |volume=72 |issue=22 |pages=5892–5895 |doi=10.1021/ja01627a034|bibcode=1955JAChS..77.5892F }}</ref> Since 1955, DMT has been [[#Endogenous DMT|found in a number of organisms]]: in at least fifty plant species belonging to ten [[Family (biology)|families]],<ref name="ott1994">{{cite book|title=Ayahuasca Analogues: Pangæan Entheogens| vauthors = Ott J |publisher=Natural Products|year=1994|isbn=978-0-9614234-5-2|edition=1st|location=[[Kennewick, WA]], USA|pages=81–83|oclc=32895480|author-link=Jonathan Ott}}</ref> and in at least four animal species, including one [[gorgonian]]<ref name="ReferenceA">{{cite journal|year=1978|title=Chemistry of Mediterranean gorgonians: simple indole derivatives from ''Paramuricea chamaeleon''|journal=Comparative Biochemistry and Physiology C|volume=61|issue=2|pages=361–362|doi=10.1016/0306-4492(78)90070-9| vauthors = Cimino G, De Stefano S }}</ref> and three mammalian species (including humans).{{citation needed|date=October 2022}}

In terms of a scientific understanding, the [[hallucinogen]]ic effects of DMT were not uncovered until 1956 by Hungarian chemist and psychiatrist [[Stephen Szára|Stephen Szara]].<ref name="Shulgin1976" /><ref name="Szara1956" /> In his paper ''Dimethyltryptamin: Its Metabolism in Man; the Relation of its Psychotic Effect to the Serotonin Metabolism'', Szara employed synthetic DMT, synthesized by the method of Speeter and Anthony, which was then administered to 20 volunteers by intramuscular injection. Urine samples were collected from these volunteers for the identification of DMT metabolites.<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 | s2cid = 7775625 }}</ref> This is considered to be the converging link between the chemical structure DMT to its cultural consumption as a psychoactive and religious sacrament.<ref name="McKennaCallawayGrob1998">{{cite journal | vauthors = McKenna DJ, Callaway JC, Grob CS | year = 1998 | title = The scientific investigation of Ayahuasca: a review of past and current research | journal = The Heffter Review of Psychedelic Research | volume = 1 | issue = 65–77| pages = 195–223 }}</ref>

Another historical milestone is the discovery of DMT in plants frequently used by Amazonian natives as additive to the vine ''[[Banisteriopsis caapi]]'' to make [[ayahuasca]] decoctions. In 1957, American chemists Francis Hochstein and Anita Paradies identified DMT in an "aqueous extract" of leaves of a plant they named ''Prestonia amazonicum'' [''sic''] and described as "commonly mixed" with ''B. caapi''.<ref>{{cite journal | vauthors = Hochstein FA, Paradies AM |year=1957 |title=Alkaloids of ''Banisteria caapi'' and ''Prestonia amazonicum'' |journal=Journal of the American Chemical Society |volume=79 |issue=21 |pages=5735–5736 |doi=10.1021/ja01578a041 |bibcode=1957JAChS..79.5735H }}</ref> The lack of a proper botanical identification of ''[[Prestonia amazonica]]'' in this study led American [[ethnobotany|ethnobotanist]] [[Richard Evans Schultes]] (1915–2001) and other scientists to raise serious doubts about the claimed plant identity.<ref>{{cite journal |vauthors=Schultes RE, Raffauf RF |year=1960 |title=''Prestonia'': An Amazon narcotic or not? |journal=Botanical Museum Leaflets, Harvard University |volume=19 |issue=5 |pages=109–122 |doi=10.5962/p.168526 |s2cid=91123988 |issn=0006-8098 |url=https://www.biodiversitylibrary.org/item/31906#page/126/mode/1up |doi-access=free |access-date=2018-01-14 |archive-date=2018-08-10 |archive-url=https://web.archive.org/web/20180810224847/https://www.biodiversitylibrary.org/item/31906#page/126/mode/1up |url-status=live }}</ref><ref name="pmid14337385">{{cite journal | vauthors = Poisson J | title = Note on "Natem", A Toxic Peruvian Beverage, and ITS Alkaloids | language = fr | journal = Annales Pharmaceutiques Françaises | volume = 23 | pages = 241–244 | date = April 1965 | pmid = 14337385 | trans-title = Note on "Natem", a toxic Peruvian beverage, and its alkaloids }}</ref> The mistake likely led the writer [[William S. Burroughs|William Burroughs]] to regard the DMT he experimented with in Tangier in 1961 as "Prestonia".<ref>{{Cite book|title=Mystery School in Hyperspace: A Cultural History of DMT| vauthors = St John G |publisher=North Atlantic Books / Evolver|year=2015|isbn=978-1-58394-732-6|location=Berkeley, CA.|page=29}}</ref> Better evidence was produced in 1965 by French pharmacologist Jacques Poisson, who isolated DMT as a sole alkaloid from leaves, provided and used by [[Aguaruna people|Aguaruna]] Indians, identified as having come from the vine ''[[Diplopterys cabrerana]]'' (then known as ''Banisteriopsis rusbyana'').<ref name="pmid14337385" /> Published in 1970, the first identification of DMT in the plant ''[[Psychotria viridis]]'',<ref name="ott1996" /> another common additive of ayahuasca, was made by a team of American researchers led by pharmacologist Ara der Marderosian.<ref>{{cite journal | vauthors = Der Marderosian AH, Kensinger KM, Chao JM, Goldstein FJ |year=1970 |title=The use and hallucinatory principles of a psychoactive beverage of the Cashinahua tribe (Amazon basin) |journal=Drug Dependence |volume=5 |pages=7–14 |issn=0070-7368 |oclc=1566975}}</ref> Not only did they detect DMT in leaves of ''P. viridis'' obtained from [[Kaxinawá]] [[indigenous people]], but they also were the first to identify it in a sample of an ayahuasca decoction, prepared by the same indigenous people.<ref name="ott1996" />