{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,11]],"date-time":"2026-09-11T14:08:54Z","timestamp":1789135734325,"version":"build-2803163510"},"reference-count":165,"publisher":"American Chemical Society (ACS)","issue":"9","license":[{"start":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T00:00:00Z","timestamp":1787011200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,11]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Isotryptamines, or 2-(1-indolyl)ethylamines, are positional or geometric isomers of tryptamines where the aminoethyl substituent has been relocated from the indole 3-position to the N1-position. Early studies with these types of agents relied on peripheral tissue assays for examination of their serotonin (5-hydroxytryptamine; 5-HT) receptor affinities to investigate structure\u2013affinity relationships. Once 5-HT receptors were identified in the brain and as the binding methodology improved, isotryptamines were further examined, including various in vitro and in vivo assays (i.e., model systems) as techniques evolved. Given that certain hallucinogenic\/psychedelic tryptamines, such as analogs of N,N-dimethyltryptamine (DMT), are currently of interest in the treatment of various neuropsychiatric disorders, there is renewed interest in agents such as isoDMT, and an isoDMT analog has now entered clinical trials. The history of isotryptamine analogs, from their discovery to the present, is reviewed.<\/jats:p>","DOI":"10.1021\/acsptsci.6c00288","type":"journal-article","created":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T13:02:21Z","timestamp":1787058141000},"page":"2379-2395","source":"Crossref","is-referenced-by-count":0,"title":["The Emergence of\nIsotryptamine Analogs as Novel Serotonergic\nAgents with Psychotherapeutic Potential"],"prefix":"10.1021","volume":"9","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3600-9045","authenticated-orcid":true,"given":"Richard A.","family":"Glennon","sequence":"first","affiliation":[{"name":"Virginia Commonwealth University , , , ,","place":["Richmond, Virginia, United States, 23298"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4349-1615","authenticated-orcid":true,"given":"Ma\u0142gorzata","family":"Dukat","sequence":"additional","affiliation":[{"name":"Virginia Commonwealth University , , , ,","place":["Richmond, Virginia, United States, 23298"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,18]]},"reference":[{"key":"2026091109132853300_cit1","doi-asserted-by":"publisher","first-page":"829","DOI":"10.1038\/s41586-025-10061-7","article-title":"Psychedelics elicit\ntheir effects by 5-HT2A receptor-mediated Gi signalling","volume":"651","author":"Xu","year":"2026","journal-title":"Nature"},{"key":"2026091109132853300_cit2","doi-asserted-by":"publisher","first-page":"111419","DOI":"10.1016\/j.pnpbp.2025.111419","article-title":"Safety\nand tolerability of N,N-dimethyltryptamine\n(DMT) in healthy volunteers and Major Depressive Disorder (MDD) patients:\nA systematic review of early-phase clinical trials","volume":"140","author":"Swieczkowski","year":"2025","journal-title":"Prog. Neuropsychopharmacol. Biol. Psychiat."},{"key":"2026091109132853300_cit3","doi-asserted-by":"publisher","first-page":"41","DOI":"10.1021\/jm00367a008","article-title":"Synthesis\nand evaluation of a novel series of N,N-dimethylisotryptamines","volume":"27","author":"Glennon","year":"1984","journal-title":"J. Med. Chem."},{"key":"2026091109132853300_cit4","first-page":"4","article-title":"Classical hallucinogens:\nAn introductory overview","volume-title":"Hallucinogens:\nan Update","author":"Glennon","year":"1994"},{"key":"2026091109132853300_cit5","doi-asserted-by":"crossref","first-page":"342","DOI":"10.1007\/978-3-642-60963-3_10","article-title":"Classical hallucinogens","volume-title":"Pharmacological Aspects of Drug Dependence.","author":"Glennon","year":"1996"},{"key":"2026091109132853300_cit6","doi-asserted-by":"publisher","first-page":"251","DOI":"10.1016\/S0091-3057(99)00045-3","article-title":"Arylalkylamine\ndrugs of abuse: An overview of drug discrimination studies","volume":"64","author":"Glennon","year":"1999","journal-title":"Pharmacol., Biochem. Behav."},{"key":"2026091109132853300_cit7","doi-asserted-by":"publisher","first-page":"288","DOI":"10.1071\/CH22256","article-title":"Quipazine: Classical\nhallucinogen? Novel psychedelic?","volume":"76","author":"Glennon","year":"2023","journal-title":"Aust. J. Chem."},{"key":"2026091109132853300_cit8","first-page":"74","article-title":"Structure-activity\nrelationships of the classic hallucinogens\nand their analogs","author":"Jacob","year":"1994","journal-title":"NIDA Res. Monogr."},{"key":"2026091109132853300_cit9","volume-title":"DMT: the Spirit Molecule","author":"Strassman","year":"2001"},{"key":"2026091109132853300_cit10","doi-asserted-by":"publisher","first-page":"418","DOI":"10.1111\/j.1749-6632.1957.tb40738.x","article-title":"A review of\nthe clinical effects of psychotomimetic agents","volume":"66","author":"Osmond","year":"1957","journal-title":"Ann. N.Y. Acad. Sci."},{"key":"2026091109132853300_cit11","volume-title":"Chemical Psychoses:\nLSD and Related Drugs","author":"Hollister","year":"1968"},{"key":"2026091109132853300_cit12","doi-asserted-by":"publisher","first-page":"592","DOI":"10.1139\/cjr31-097","article-title":"Synthesis\nof the methyltryptamines and some derivatives Can","volume":"5","author":"Manske","year":"1931","journal-title":"J. Res."},{"key":"2026091109132853300_cit13","first-page":"201","article-title":"DMT at fifty","volume":"9","author":"Sza\u0301ra","year":"2007","journal-title":"Neuropsychopharmacol. Hung."},{"key":"2026091109132853300_cit14","doi-asserted-by":"publisher","first-page":"617","DOI":"10.1002\/dta.422","article-title":"A critical review of reports of endogenous\npsychedelic N,N-dimethyltryptamines in humans: 1955\u20132010","volume":"4","author":"Barker","year":"2012","journal-title":"Drug Test. Anal."},{"key":"2026091109132853300_cit15","doi-asserted-by":"publisher","first-page":"29","DOI":"10.1080\/02791072.1991.10472572","article-title":"Human hallucinogenic\ndrug research in the United States: A present-day case history and\nreview of the process","volume":"23","author":"Strassman","year":"1991","journal-title":"J. Psychoact. Drugs"},{"key":"2026091109132853300_cit16","first-page":"92","article-title":"Human hallucinogenic\ndrug research: Regulatory, clinical, and scientific issues","volume-title":"Hallucinogens; An Update.","author":"Strassman","year":"1994"},{"key":"2026091109132853300_cit17","doi-asserted-by":"publisher","first-page":"1268","DOI":"10.1177\/0269881116662634","article-title":"Survey study of challenging experiences\nafter ingesting psilocybin mushrooms: Acute and enduring positive\nand negative consequences","volume":"30","author":"Carbonaro","year":"2016","journal-title":"J. Psychopharmacol."},{"key":"2026091109132853300_cit18a","doi-asserted-by":"publisher","first-page":"843","DOI":"10.1001\/jama.2023.14530","article-title":"Single-dose\npsilocybin treatment for major depressive disorder: A randomized clinical\ntrial","volume":"330","author":"Raison","year":"2023","journal-title":"JAMA"},{"key":"2026091109132853300_cit18b","doi-asserted-by":"publisher","first-page":"710","DOI":"10.1001\/jama.2024.0828","article-title":"Error in Byline","volume":"331","author":"Raison","year":"2024","journal-title":"Erratum in: JAMA"},{"key":"2026091109132853300_cit19","doi-asserted-by":"publisher","first-page":"3129","DOI":"10.1016\/j.neuron.2025.06.012","article-title":"The\npolypharmacology of psychedelics reveals\nmultiple targets for potential therapeutics","volume":"113","author":"Jain","year":"2025","journal-title":"Neuron"},{"key":"2026091109132853300_cit20","doi-asserted-by":"publisher","first-page":"209","DOI":"10.1002\/cpt.557","article-title":"Psychedelics\nas medicines: An emerging\nnew paradigm","volume":"101","author":"Nichols","year":"2017","journal-title":"Clin. 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Med."},{"key":"2026091109132853300_cit27","volume-title":"TIHKAL.","author":"Shulgin","year":"1997"},{"key":"2026091109132853300_cit28","unstructured":"Trout Notes, Some Simple Tryptamines.\n          \n          2nd\n          Mydriatic Productions, 2007. https:\/\/troutsnotes.com\/pdf\/SomeSimpleTryptamines_2ndEd_2007_with_addendum.pdf)."},{"key":"2026091109132853300_cit29","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1007\/7854_2017_475","article-title":"Chemistry\nand structure-activity relationships of psychedelics","volume":"36","author":"Nichols","year":"2017","journal-title":"Curr. Top Behav. Neurosci."},{"key":"2026091109132853300_cit30","doi-asserted-by":"publisher","first-page":"3375","DOI":"10.1016\/S0040-4039(00)99767-3","article-title":"Photochemical synthesis of 2-(2-aminoethyl)indole (isotryptamine)\nderivatives","volume":"10","author":"Snieckus","year":"1969","journal-title":"Tetrahedron Lett."},{"key":"2026091109132853300_cit31","first-page":"851","article-title":"Synthesis\nand pharmacologic properties\nof pyridoyl derivatives of 3-methylaminoindole 2-methyltryptamine\nand isotryptamine","volume":"2","author":"Misztal","year":"1976","journal-title":"Arch. Immunol. Ther. Exp."},{"issue":"I","key":"2026091109132853300_cit32","doi-asserted-by":"publisher","first-page":"72","DOI":"10.1007\/BF00471201","article-title":"Synthesis\nof isotryptamines and tetrahydro-\u03b3-carbolines from 2-indolylacetic\nacid derivatives","author":"Trofimov","year":"1979","journal-title":"Chem. Heterocycl. Compd."},{"key":"2026091109132853300_cit33","first-page":"63","article-title":"Some central effects\nof tiflucarbine, a new potential antidepressant drug","volume":"39","author":"Maj","year":"1987","journal-title":"Pol. J. Pharmacol. Pharm."},{"key":"2026091109132853300_cit34","doi-asserted-by":"publisher","first-page":"1589","DOI":"10.1021\/acs.orglett.8b00332","article-title":"Double \u201copen and shut\u201d transformation\nof \u03b3-carbolines triggered by ammonium salts: One-pot synthesis\nof multiheterocyclic compounds","volume":"20","author":"Abe","year":"2018","journal-title":"Org. Lett."},{"key":"2026091109132853300_cit35","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1080\/00304949609355907","article-title":"Synthesis\nof \u03b2-carbolines. A review","volume":"28","author":"Love","year":"1996","journal-title":"Org. Prep.\nProced. Int."},{"key":"2026091109132853300_cit36","doi-asserted-by":"publisher","first-page":"12128","DOI":"10.1021\/acs.joc.0c01344","article-title":"Synthesis of 2-(1H-Indol-2-yl)acetamides via Br\u00f8nsted acid-assisted cyclization\ncascade","volume":"85","author":"Aksenov","year":"2020","journal-title":"J. Org. Chem."},{"key":"2026091109132853300_cit37","first-page":"201","article-title":"5-Hydroxytryptamine\nand non-vascular smooth muscle contraction and relaxation","volume-title":"The Peripheral Actions of 5-Hydroxytryptamine","author":"Cohen","year":"1989"},{"key":"2026091109132853300_cit38","doi-asserted-by":"publisher","first-page":"344","DOI":"10.1111\/j.1476-5381.1957.tb00146.x","article-title":"A sensitive\nmethod for the assay of 5-hydroxytryptamine","volume":"12","author":"Vane","year":"1957","journal-title":"Br. J. Pharmacol. Chemother."},{"key":"2026091109132853300_cit39","volume-title":"Quantitative Aspects\nof Chemical Pharmacology","author":"Barlow","year":"1980"},{"key":"2026091109132853300_cit40","doi-asserted-by":"publisher","first-page":"87","DOI":"10.1111\/j.1476-5381.1959.tb00933.x","article-title":"The relative\nactivities of some tryptamine analogues on the isolated rat stomach\nstrip preparation","volume":"14","author":"Vane","year":"1959","journal-title":"Br. J. Pharmacol. Chemother."},{"key":"2026091109132853300_cit41","doi-asserted-by":"publisher","first-page":"265","DOI":"10.1111\/j.1476-5381.1959.tb01397.x","article-title":"Actions of some analogues\nof 5-hydroxytryptamine on the isolated\nrat uterus and the rat fundus strip preparations","volume":"14","author":"Barlow","year":"1959","journal-title":"Br. J. Pharmacol. Chemother."},{"key":"2026091109132853300_cit42","doi-asserted-by":"publisher","first-page":"856","DOI":"10.1021\/jm00317a022","article-title":"Synthesis\nof some 3-indenealkylamines.\nComparison of the biological activity of 3-indenealkylamines and 3-benzo[b]thiophenealkylamines\nwith their tryptamine isosteres","volume":"10","author":"Winter","year":"1967","journal-title":"J. Med. Chem."},{"key":"2026091109132853300_cit43","first-page":"453","article-title":"The electronic and\nserotonin receptor binding affinity\nproperties of N,N-dimethyltryptamine analogs","volume":"18","author":"Glennon","year":"1977","journal-title":"Res. Commun. Chem. Pathol. Pharmacol."},{"key":"2026091109132853300_cit44","doi-asserted-by":"publisher","first-page":"428","DOI":"10.1021\/jm00190a014","article-title":"Serotonin receptor binding affinities\nof tryptamine\nanalogues","volume":"22","author":"Glennon","year":"1979","journal-title":"J. Med. Chem."},{"key":"2026091109132853300_cit45","doi-asserted-by":"publisher","first-page":"68","DOI":"10.1021\/jm00343a013","article-title":"2,3-Dihydro and\ncarbocyclic analogues of tryptamines: Interaction with serotonin receptors","volume":"25","author":"Glennon","year":"1982","journal-title":"J. Med. Chem."},{"key":"2026091109132853300_cit46","first-page":"253","article-title":"Involvement\nof serotonin in the action of hallucinogenic agents","volume-title":"Neuropharmacology of Serotonin","author":"Glennon","year":"1985"},{"key":"2026091109132853300_cit47","doi-asserted-by":"publisher","first-page":"822","DOI":"10.1021\/jm00206a022","article-title":"Serotonin receptor\nbinding affinities\nof several hallucinogenic phenalkylamine and N,N-dimethyltryptamine\nanalogs","volume":"21","author":"Glennon","year":"1978","journal-title":"J. Med. Chem."},{"key":"2026091109132853300_cit48","doi-asserted-by":"publisher","first-page":"1163","DOI":"10.1021\/jm00352a013","article-title":"Behavioral and serotonin\nreceptor properties of 4-substituted derivatives of the hallucinogen\n1-(2,5-dimethoxyphenyl)-2-aminopropane","volume":"25","author":"Glennon","year":"1982","journal-title":"J. Med.\nChem."},{"key":"2026091109132853300_cit49","doi-asserted-by":"publisher","first-page":"1722","DOI":"10.1021\/acsptsci.4c00157","article-title":"1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane (DOI): From an obscure\nto pivotal member of the DOX family of serotonergic psychedelic agents\n- A Review","volume":"7","author":"Glennon","year":"2024","journal-title":"ACS Pharmacol. Transl. Sci."},{"key":"2026091109132853300_cit50","doi-asserted-by":"publisher","first-page":"294","DOI":"10.1021\/jm00177a017","article-title":"Serotonin receptor\naffinities of psychoactive phenalkylamine analogues","volume":"23","author":"Glennon","year":"1980","journal-title":"J. Med. Chem"},{"key":"2026091109132853300_cit51","doi-asserted-by":"publisher","first-page":"687","DOI":"10.1016\/S0026-895X(25)13812-1","article-title":"Multiple serotonin receptors: Differential binding\nof [3H]5-hydroxytryptamine, [3H]lysergic acid\ndiethylamide and [3H]spiroperidol","volume":"16","author":"Peroutka","year":"1979","journal-title":"Mol. Pharmacol."},{"key":"2026091109132853300_cit52","doi-asserted-by":"publisher","first-page":"310","DOI":"10.1124\/pr.118.015552","article-title":"International\nUnion of Basic and Clinical Pharmacology. CX. Classification of receptors\nfor 5-hydroxytryptamine; pharmacology and function","volume":"73","author":"Barnes","year":"2021","journal-title":"Pharmacol. Rev."},{"key":"2026091109132853300_cit53","doi-asserted-by":"publisher","first-page":"549","DOI":"10.1016\/S0026-895X(25)08969-2","article-title":"Molecular\ncloning, functional expression, and pharmacological characterization\nof a novel serotonin receptor (5-hydroxytryptamine2F) from\nrat stomach fundus","volume":"42","author":"Kursar","year":"1992","journal-title":"Mol. Pharmacol."},{"key":"2026091109132853300_cit54","doi-asserted-by":"publisher","first-page":"419","DOI":"10.1016\/S0026-895X(25)13628-6","article-title":"Pharmacological\ncharacteristics of the newly cloned rat 5-hydroxytryptamine2F receptor","volume":"43","author":"Wainscott","year":"1993","journal-title":"Mol. Pharmacol."},{"key":"2026091109132853300_cit55","doi-asserted-by":"publisher","first-page":"145","DOI":"10.1016\/0014-2999(85)90486-8","article-title":"[3H]DOB: A specific agonist radioligand\nfor 5-HT2 serotonin\nreceptors","volume":"117","author":"Titeler","year":"1985","journal-title":"Eur. J. Pharmacol."},{"key":"2026091109132853300_cit56","doi-asserted-by":"publisher","first-page":"5","DOI":"10.1021\/jm00396a003","article-title":"[125I]-1-(2,5-Dimethoxy-4-iodophenyl)-2-amino-propane:\nAn iodinated radioligand that specifically labels the agonist high-affinity\nstate of 5-HT2 serotonin receptors","volume":"31","author":"Glennon","year":"1988","journal-title":"J. Med. Chem."},{"key":"2026091109132853300_cit57","doi-asserted-by":"publisher","first-page":"843","DOI":"10.1016\/S0022-3565(25)23167-6","article-title":"Autoradiographic characterization of (\u00b1)-1-(2,5-dimethoxy-4-[125I] iodophenyl)-2-aminopropane ([125I]DOI) binding\nto 5-HT2 and 5-HT1c receptors in rat brain","volume":"255","author":"Appel","year":"1990","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"2026091109132853300_cit58","doi-asserted-by":"publisher","first-page":"1803","DOI":"10.1016\/0028-3908(87)90138-9","article-title":"Binding to the serotonin\n5-HT2 receptor by the enantiomers of 125I-DOI","volume":"26","author":"Johnson","year":"1987","journal-title":"Neuropharmacology"},{"key":"2026091109132853300_cit59","doi-asserted-by":"publisher","first-page":"155","DOI":"10.1016\/S0960-894X(01)00713-2","article-title":"Evaluation\nof isotryptamine\nderivatives at 5-HT2 serotonin receptors","volume":"12","author":"Chang-Fong","year":"2002","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"2026091109132853300_cit60","doi-asserted-by":"publisher","first-page":"291","DOI":"10.1016\/0014-2999(88)90432-3","article-title":"Indolealkylamine\nanalogs share 5-HT2 binding characteristics with phenylalkylamine\nhallucinogens","volume":"145","author":"Lyon","year":"1988","journal-title":"Eur. J. Pharmacol."},{"key":"2026091109132853300_cit61","doi-asserted-by":"publisher","first-page":"722","DOI":"10.1002\/cpt196126722","article-title":"Effects in normal\nman of alpha-methyltryptamine and alpha-ethyltryptamine","volume":"2","author":"Murphree","year":"1961","journal-title":"Clin. Pharmacol. Ther."},{"key":"2026091109132853300_cit62","doi-asserted-by":"publisher","first-page":"1487","DOI":"10.1016\/0024-3205(79)90032-8","article-title":"The effect\nof chirality on serotonin receptor affinity","volume":"24","author":"Glennon","year":"1979","journal-title":"Life Sci."},{"key":"2026091109132853300_cit63","doi-asserted-by":"publisher","first-page":"2762","DOI":"10.1021\/jm970030l","article-title":"Novel agonists of 5HT2C receptors. Synthesis and biological evaluation of substituted 2-(indol-1-yl)-1-methylethylamines\nand 2-(indeno[1,2-b]pyrrol-1-yl)-1-methylethylamines. Improved therapeutics\nfor obsessive compulsive disorder","volume":"40","author":"Bo\u0308s","year":"1997","journal-title":"J. Med. Chem."},{"key":"2026091109132853300_cit64","doi-asserted-by":"publisher","first-page":"114","DOI":"10.1007\/s00210-004-0951-4","article-title":"Pharmacological\ncharacterization\nof the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and\n5-HT(2C) receptors","volume":"370","author":"Knight","year":"2004","journal-title":"Naunyn-Schmiedebergs Arch.\nPharmacol."},{"key":"2026091109132853300_cit65","doi-asserted-by":"publisher","first-page":"274","DOI":"10.1037\/a0036595","article-title":"Abuse-related effects of dual dopamine\/serotonin\nreleasers with varying potency to release norepinephrine in male rats\nand rhesus monkeys","volume":"22","author":"Banks","year":"2014","journal-title":"Exp. Clin. 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Ther."},{"key":"2026091109132853300_cit143","doi-asserted-by":"publisher","first-page":"1585","DOI":"10.1007\/s00213-023-06482-9","article-title":"Serotonin\n2C receptors are also important in head-twitch responses in male mice","volume":"242","author":"Custodio","year":"2025","journal-title":"Psychopharmacology"},{"key":"2026091109132853300_cit144","doi-asserted-by":"publisher","first-page":"4458","DOI":"10.1021\/acschemneuro.4c00513","article-title":"Serotonin\n1A receptors modulate serotonin 2A receptor-mediated behavioral effects\nof 5-methoxy-N,N-dimethyltryptamine analogs in mice","volume":"15","author":"Glatfelter","year":"2024","journal-title":"ACS Chem. 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Commun."},{"key":"2026091109132853300_cit156","doi-asserted-by":"publisher","first-page":"439","DOI":"10.1016\/j.neuron.2007.01.008","article-title":"Hallucinogens recruit specific cortical\n5-HT(2A) receptor-mediated signaling pathways to affect behavior","volume":"53","author":"Gonza\u0301lez-Maeso","year":"2007","journal-title":"Neuron"},{"key":"2026091109132853300_cit157","doi-asserted-by":"publisher","first-page":"257","DOI":"10.1007\/7854_2016_461","article-title":"Serotonergic hallucinogen-induced\nvisual perceptual alterations","volume":"36","author":"Kometer","year":"2016","journal-title":"Curr. Top Behav.\nNeurosci."},{"key":"2026091109132853300_cit158","doi-asserted-by":"publisher","first-page":"451","DOI":"10.1016\/j.cub.2016.12.030","article-title":"The fabric\nof meaning and subjective effects in LSD-induced\nstates depend on serotonin 2A receptor activation","volume":"27","author":"Preller","year":"2017","journal-title":"Curr. Biol."},{"key":"2026091109132853300_cit159","doi-asserted-by":"publisher","first-page":"121","DOI":"10.1055\/a-1721-2914","article-title":"Classic\npsychedelic drugs: Update\non biological mechanisms","volume":"55","author":"Vollenweider","year":"2022","journal-title":"Pharmacopsychiatry"},{"key":"2026091109132853300_cit160","first-page":"192","volume-title":"Psychedelic Drugs\nReconsidered","author":"Grinspoon","year":"1997"},{"key":"2026091109132853300_cit161","doi-asserted-by":"publisher","first-page":"1407","DOI":"10.1038\/s41593-022-01177-4","article-title":"The neural\nbasis of psychedelic action","volume":"25","author":"Kwan","year":"2022","journal-title":"Nat. Neurosci."},{"key":"2026091109132853300_cit162","doi-asserted-by":"publisher","first-page":"449","DOI":"10.1038\/s41591-025-04194-5","article-title":"The science of psychedelic medicine","volume":"32","author":"Siegel","year":"2026","journal-title":"Nat. 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