{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,29]],"date-time":"2026-10-29T23:22:51Z","timestamp":1793316171721,"version":"4.5.0"},"reference-count":23,"publisher":"American Chemical Society (ACS)","issue":"5","license":[{"start":{"date-parts":[[2018,5,7]],"date-time":"2018-05-07T00:00:00Z","timestamp":1525651200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"funder":[{"name":"Department of Chemistry, University of California, Davis"},{"name":"Science Translation and Innovative Research, University of California, Davis"},{"name":"Department of Biochemistry and Molecular Medicine, University of California, University of California, Davis"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2018,5,31]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>A large number of clinically used drugs and experimental pharmaceuticals possess the N,N-dimethyltryptamine (DMT) structural core. Previous reports have described the reaction of this motif with dichloromethane (DCM), a common laboratory solvent used during extraction and purification, leading to the formation of an undesired quaternary ammonium salt byproduct. However, the kinetics of this reaction under various conditions have not been thoroughly described. Here, we report a series of experiments designed to simulate the exposure of DMT to DCM that would take place during extraction from plant material, biphasic aqueous work-up, or column chromatography purification. We find that the quaternary ammonium salt byproduct forms at an exceedingly slow rate, only accumulates to a significant extent upon prolonged exposure of DMT to DCM, and is readily extracted into water. Our results suggest that DMT can be exposed to DCM under conditions where contact times are limited (&amp;lt;30 min) with minimal risk of degradation and that this byproduct is not observed following aqueous extraction. However, alternative solvents should be considered when the experimental conditions require longer contact times. Our work has important implications for preparing a wide-range of pharmaceuticals bearing the DMT structural motif in high yields and purities.<\/jats:p>","DOI":"10.1021\/acsomega.8b00507","type":"journal-article","created":{"date-parts":[[2018,5,7]],"date-time":"2018-05-07T10:36:42Z","timestamp":1525689402000},"page":"4968-4973","source":"Crossref","is-referenced-by-count":17,"title":["Reaction of\n                    <i>N<\/i>\n                    ,\n                    <i>N<\/i>\n                    -Dimethyltryptamine with Dichloromethane\nUnder Common Experimental Conditions"],"prefix":"10.1021","volume":"3","author":[{"given":"Lee E.","family":"Dunlap","sequence":"first","affiliation":[{"name":"University of California, Davis , , One Shields Avenue , , ,","place":["Davis, California, United States, 95616"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4517-0543","authenticated-orcid":true,"given":"David E.","family":"Olson","sequence":"additional","affiliation":[{"name":"University of California, Davis , , One Shields Avenue , , ,","place":["Davis, California, United States, 95616"]},{"name":"University of California, Davis , , 2700 Stockton Blvd, Suite 2102 , , ,","place":["Sacramento, California, United States, 95817"]},{"name":"University of California, Davis , , 1544 Newton Ct , , ,","place":["Davis, California, United States, 95618"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2018,5,7]]},"reference":[{"key":"2026090319080837600_cit1","doi-asserted-by":"publisher","first-page":"111","DOI":"10.1016\/j.pharmthera.2004.03.002","article-title":"Clinical\ninvestigations of the therapeutic potential of ayahuasca: rationale\nand regulatory challenges","volume":"102","author":"McKenna","year":"2004","journal-title":"Pharmacol. 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Psiquiatr."},{"key":"2026090319080837600_cit5","doi-asserted-by":"publisher","first-page":"351","DOI":"10.1016\/s0006-3223(99)00230-9","article-title":"Antidepressant effects of ketamine\nin depressed patients","volume":"47","author":"Berman","year":"2000","journal-title":"Biol. Psychiatry"},{"key":"2026090319080837600_cit6","doi-asserted-by":"publisher","DOI":"10.1021\/acschemneuro.8b00134","article-title":"Effects of N,N-Dimethyltryptamine\n(DMT) on Rat Behaviors\nRelevant to Anxiety and Depression","author":"Cameron","year":"2018","journal-title":"ACS Chem.\nNeurosci."},{"key":"2026090319080837600_cit7","doi-asserted-by":"publisher","first-page":"193","DOI":"10.1177\/2045125316638008","article-title":"Antidepressive, anxiolytic, and antiaddictive\neffects of ayahuasca, psilocybin and lysergic acid diethylamide (LSD):\na systematic review of clinical trials published in the last 25 years","volume":"6","author":"dos Santos","year":"2016","journal-title":"Ther. Adv. Psychopharmacol."},{"key":"2026090319080837600_cit8","first-page":"1","article-title":"Ibogaine: a\nreview","volume-title":"The Alkaloids: Chemistry and Biology","author":"Alper","year":"2001"},{"key":"2026090319080837600_cit9","doi-asserted-by":"publisher","first-page":"992","DOI":"10.1016\/j.tips.2017.08.003","article-title":"Psychedelic\nDrugs in Biomedicine","volume":"38","author":"Kyzar","year":"2017","journal-title":"Trends Pharmacol. Sci."},{"key":"2026090319080837600_cit10","doi-asserted-by":"publisher","first-page":"221","DOI":"10.1111\/head.12601","article-title":"Triptans in the Acute\nTreatment of Migraine: A Systematic Review and Network Meta-Analysis","volume":"55","author":"Cameron","year":"2015","journal-title":"Headache"},{"key":"2026090319080837600_cit11","doi-asserted-by":"publisher","first-page":"7901","DOI":"10.1021\/acs.jmedchem.5b00179","article-title":"Therapeutic Potential\nof 5-HT6 Receptor\nAgonists","volume":"58","author":"Karila","year":"2015","journal-title":"J. Med. Chem."},{"key":"2026090319080837600_cit12","doi-asserted-by":"publisher","first-page":"359","DOI":"10.1002\/mrc.1959","article-title":"NMR spectral\nassignments\nof a new chlorotryptamine alkaloid and its analogues from Acacia confuse","volume":"45","author":"Buchanan","year":"2007","journal-title":"Magn. Reson. Chem."},{"key":"2026090319080837600_cit13","doi-asserted-by":"publisher","first-page":"207","DOI":"10.1016\/j.jpba.2007.12.024","article-title":"N,N-Dimethyltryptamine\nand dichloromethane:\nrearrangement of quaternary ammonium salt product during GC-EI and\nCI-MS-MS analysis","volume":"47","author":"Brandt","year":"2008","journal-title":"J. Pharm. Biomed. Anal."},{"key":"2026090319080837600_cit14","doi-asserted-by":"publisher","first-page":"162","DOI":"10.1016\/j.forsciint.2008.03.013","article-title":"Halogenated\nsolvent interactions\nwith N,N-dimethyltryptamine: Formation of quaternary ammonium salts\nand their artificially induced rearrangements during analysis","volume":"178","author":"Brandt","year":"2008","journal-title":"Forensic Sci. Int."},{"key":"2026090319080837600_cit15","doi-asserted-by":"publisher","first-page":"1517","DOI":"10.1021\/op4002565","article-title":"Sanofi\u2019s\nSolvent Selection\nGuide: A Step Toward More Sustainable Processes","volume":"17","author":"Prat","year":"2013","journal-title":"Org. Process Res. Dev."},{"key":"2026090319080837600_cit16","doi-asserted-by":"publisher","first-page":"854","DOI":"10.1039\/c0gc00918k","article-title":"Expanding GSK\u2019s\nsolvent selection\nguide \u2013 embedding sustainability into solvent selection starting\nat medicinal chemistry","volume":"13","author":"Henderson","year":"2011","journal-title":"Green Chem."},{"key":"2026090319080837600_cit17","first-page":"57","article-title":"The Reactions\nof Heterocyclic Compounds with Carbenes","volume-title":"Advances\nin Heterocyclic Chemistry","author":"Rees","year":"1964"},{"key":"2026090319080837600_cit18","doi-asserted-by":"publisher","first-page":"31","DOI":"10.1039\/b711717e","article-title":"Green chemistry\ntools to influence\na medicinal chemistry and research chemistry based organization","volume":"10","author":"Alfonsi","year":"2008","journal-title":"Green Chem."},{"key":"2026090319080837600_cit19","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/14356007.a06_233.pub2","article-title":"Chlorinated\nHydrocarbons","volume-title":"Ullmann\u2019s Encyclopedia\nof Industrial Chemistry","author":"Rossberg","year":"2006"},{"key":"2026090319080837600_cit20","doi-asserted-by":"publisher","first-page":"1857","DOI":"10.1021\/jo00385a038","article-title":"Reaction of amines with methylene chloride. Evidence for rapid aminal\nformation from N-methylenepyrrolidinium chloride and pyrrolidine","volume":"52","author":"Mills","year":"1987","journal-title":"J. Org. Chem."},{"key":"2026090319080837600_cit21","doi-asserted-by":"publisher","first-page":"469","DOI":"10.3891\/acta.chem.scand.38b-0469","article-title":"Solvent Properties of Dichloromethane. II. The Reactivity\nof Dichloromethane Toward Amines","volume":"38","author":"Nevstad","year":"1984","journal-title":"Acta Chem.\nScand., Ser. B"},{"key":"2026090319080837600_cit22","doi-asserted-by":"publisher","first-page":"107","DOI":"10.1002\/pca.893","article-title":"Studies on tropane alkaloid extraction by volatile\norganic solvents: dichloromethane vs. chloroform","volume":"17","author":"El Jaber-Vazdekis","year":"2006","journal-title":"Phytochem. Anal."},{"key":"2026090319080837600_cit23","doi-asserted-by":"publisher","first-page":"1035","DOI":"10.1039\/jr9560001035","article-title":"Kinetics\nof the Reaction between Methyl Iodide and\nTrimethylamine in Carbon Tetrachloride Solution","author":"Fahim","year":"1956","journal-title":"J. Chem. Soc."}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.8b00507","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/3\/5\/4968\/68316230\/acsomega.8b00507.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/3\/5\/4968\/68316230\/acsomega.8b00507.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,4]],"date-time":"2026-09-04T08:11:01Z","timestamp":1788509461000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/3\/5\/4968\/749797\/Reaction-of-N-N-Dimethyltryptamine-with"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,5,7]]},"references-count":23,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2018,5,7]]},"published-print":{"date-parts":[[2018,5,31]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.8b00507","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,5,7]]}}}