Editing N,N-Dimethyltryptamine (section)

===Laboratory synthesis===
DMT can be synthesized through several possible pathways from different starting materials. The two most commonly encountered synthetic routes are through the reaction of [[indole]] with [[oxalyl chloride]] followed by reaction with [[dimethylamine]] and reduction of the [[carbonyl]] functionalities with [[lithium aluminium hydride]] to form DMT.<ref name="TiHKAL" /> The second commonly encountered route is through the ''N'',''N''-dimethylation of tryptamine using [[formaldehyde]] followed by reduction with [[sodium cyanoborohydride]] or [[sodium triacetoxyborohydride]]. [[Sodium borohydride]] can be used but requires a larger excess of reagents and lower temperatures due to it having a higher selectivity for carbonyl groups as opposed to [[imines]].<ref>{{cite journal | vauthors = Bosch J, Roca T, Armengol M, Fernández-Forner D |title=Synthesis of 5-(sulfamoylmethyl)indoles |journal=Tetrahedron |date=4 February 2001 |volume=57 |issue=6 |pages=1041–1048 |doi=10.1016/S0040-4020(00)01091-7 }}</ref>  Procedures using sodium cyanoborohydride and sodium triacetoxyborohydride (presumably created ''in situ'' from cyanoborohydride though this may not be the case due to the presence of water or [[methanol]]) also result in the creation of cyanated tryptamine and [[Beta-carboline|''beta''-carboline]] byproducts of unknown toxicity while using sodium borohydride in absence of acid does not.<ref>{{cite journal | vauthors = Brandt SD, Moore SA, Freeman S, Kanu AB | title = Characterization of the synthesis of ''N'',''N''-dimethyltryptamine by reductive amination using gas chromatography ion trap mass spectrometry | journal = Drug Testing and Analysis | volume = 2 | issue = 7 | pages = 330–338 | date = July 2010 | pmid = 20648523 | doi = 10.1002/dta.142 }}</ref> Bufotenine, a plant extract, can also be synthesized into DMT.<ref>{{cite journal | vauthors = Moreira LA, Murta MM, Gatto CC, Fagg CW, dos Santos ML | title = Concise synthesis of ''N'',''N''-dimethyltryptamine and 5-methoxy-''N'',''N''-dimethyltryptamine starting with bufotenine from Brazilian Anadenanthera ssp | journal = Natural Product Communications | volume = 10 | issue = 4 | pages = 581–584 | date = April 2015 | pmid = 25973481 | doi = 10.1177/1934578X1501000411 | s2cid = 34076965 | doi-access = free }}</ref> 

Alternatively, an excess of [[methyl iodide]] or [[Methyl p-toluenesulfonate|methyl ''p''-toluenesulfonate]] and [[sodium carbonate]] can be used to over-methylate tryptamine, resulting in the creation of a [[quaternary ammonium salt]], which is then dequaternized (demethylated) in [[ethanolamine]] to yield DMT. The same two-step procedure is used to synthesize other ''N'',''N''-dimethylated compounds, such as 5-MeO-DMT.<ref>{{cite web | url=https://hyperlab.info/inv/index.php?lang=en&act=ST&f=17&t=913&st=120 | title=Hyperlab.info -> Мелатонин и 5-MeO-DMT | access-date=2023-09-27 | archive-date=2023-09-27 | archive-url=https://web.archive.org/web/20230927010145/https://hyperlab.info/inv/index.php?lang=en&act=ST&f=17&t=913&st=120 | url-status=live }}</ref>