Isotryptamine

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| IUPACName = 2-indol-1-ylethanamine

| OtherNames = 2-Indolylethylamine; 2-(1-Indolyl)ethylamine; 2-(1H-Indol-1-yl)ethanamine

| Section1 = {{Chembox Identifiers

| CASNo = 13708-58-2

| ChemSpiderID = 227015

| InChI = 1S/C10H12N2/c11-6-8-12-7-5-9-3-1-2-4-10(9)12/h1-5,7H,6,8,11H2

| InChIKey = BXEFQUSYBZYTAE-UHFFFAOYSA-N

| PubChem = 258690

| SMILES = C1=CC=C2C(=C1)C=CN2CCN

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| Section2 = {{Chembox Properties

| C=10 | H=12 | N=2

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| Section3 = {{Chembox Hazards

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Isotryptamine, also known as 2-(1-indolyl)ethylamine, is a chemical compound and positional isomer of tryptamine (2-(3-indolyl)ethylamine).{{cite web | title=2-(1H-indol-1-yl)ethanamine | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/258690 | access-date=14 November 2024}}

A variety of isotryptamine derivatives, or substituted isotryptamines, have been developed, including serotonergic psychedelics and psychoplastogens like 6-MeO-isoDMT;{{cite journal | vauthors = Glennon RA, Jacyno JM, Young R, McKenney JD, Nelson D | title = Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines | journal = J Med Chem | volume = 27 | issue = 1 | pages = 41–45 | date = January 1984 | pmid = 6581313 | doi = 10.1021/jm00367a008 | url = }}{{cite journal | vauthors = Dunlap LE, Azinfar A, Ly C, Cameron LP, Viswanathan J, Tombari RJ, Myers-Turnbull D, Taylor JC, Grodzki AC, Lein PJ, Kokel D, Olson DE | title = Identification of Psychoplastogenic N,N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure-Activity Relationship Studies | journal = J Med Chem | volume = 63 | issue = 3 | pages = 1142–1155 | date = February 2020 | pmid = 31977208 | doi = 10.1021/acs.jmedchem.9b01404 | pmc = 7075704 | url = }} non-hallucinogenic psychoplastogens like isoDMT, 5-MeO-isoDMT, and zalsupindole (DLX-001; AAZ-A-154);{{cite journal | vauthors = Duan W, Cao D, Wang S, Cheng J | title = Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants | journal = Chem Rev | volume = 124 | issue = 1 | pages = 124–163 | date = January 2024 | pmid = 38033123 | doi = 10.1021/acs.chemrev.3c00375 | url = }}{{cite journal | vauthors = Atiq MA, Baker MR, Voort JL, Vargas MV, Choi DS | title = Disentangling the acute subjective effects of classic psychedelics from their enduring therapeutic properties | journal = Psychopharmacology (Berl) | volume = | issue = | pages = | date = May 2024 | pmid = 38743110 | doi = 10.1007/s00213-024-06599-5 | url = | doi-access = free }}{{cite journal | vauthors = Rasmussen K, Chytil M, Agrawal R, Leach P, Gillie D, Mungenast A, Vancutsem P, Engel S, Meyer R, Koenig A, Rus M | title=14. Preclinical Pharmacology of DLX-001, a Novel Non-Hallucinogenic Neuroplastogen With the Potential for Treating Neuropsychiatric Diseases | journal=Biological Psychiatry | publisher=Elsevier BV | volume=95 | issue=10 | year=2024 | issn=0006-3223 | doi=10.1016/j.biopsych.2024.02.192 | page=S80}}{{cite journal | vauthors = Rasmussen K, Engel S, Chytil M, Koenig A, Meyer R, Rus M, Olson D, Salinas E | title = ACNP 62nd Annual Meeting: Poster Abstracts P251 - P500: P361. Preclinical Pharmacology of DLX-001, a Novel Non-Hallucinogenic Neuroplastogen With the Potential for Treating Neuropsychiatric Diseases | journal = Neuropsychopharmacology | volume = 48 | issue = Suppl 1 | pages = 211–354 (274–275) | date = December 2023 | pmid = 38040810 | pmc = 10729596 | doi = 10.1038/s41386-023-01756-4 | url = }} serotonin 5-HT_2C receptor agonists like (S)-5,6-difluoro-isoAMT, Ro60-0175 ((S)-5-fluoro-6-chloro-isoAMT), and PNU-181731;{{cite journal | vauthors = Chang-Fong J, Addo J, Dukat M, Smith C, Mitchell NA, Herrick-Davis K, Teitler M, Glennon RA | title = Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors | journal = Bioorg Med Chem Lett | volume = 12 | issue = 2 | pages = 155–158 | date = January 2002 | pmid = 11755343 | doi = 10.1016/s0960-894x(01)00713-2 | url = }}{{cite journal | last1=Bishop | first1=Michael J | last2=Nilsson | first2=Björn M | title=New 5-HT2C receptor agonists | journal=Expert Opinion on Therapeutic Patents | volume=13 | issue=11 | date=2003 | issn=1354-3776 | doi=10.1517/13543776.13.11.1691 | pages=1691–1705}}{{cite journal | last1=Dutton | first1=Alice C. | last2=Barnes | first2=Nicholas M. | title=Anti-obesity pharmacotherapy: Future perspectives utilising 5-HT2C receptor agonists | journal=Drug Discovery Today: Therapeutic Strategies | volume=3 | issue=4 | date=2006 | doi=10.1016/j.ddstr.2006.11.005 | pages=577–583}}{{cite journal | vauthors = Nilsson BM | title = 5-Hydroxytryptamine 2C (5-HT2C) receptor agonists as potential antiobesity agents | journal = J Med Chem | volume = 49 | issue = 14 | pages = 4023–4034 | date = July 2006 | pmid = 16821762 | doi = 10.1021/jm058240i | url = }}{{cite journal | vauthors = Lee J, Jung ME, Lee J | title = 5-HT2C receptor modulators: a patent survey | journal = Expert Opin Ther Pat | volume = 20 | issue = 11 | pages = 1429–1455 | date = November 2010 | pmid = 20849206 | doi = 10.1517/13543776.2010.518956 | url = }} serotonin 5-HT₆ receptor modulators;{{cite journal | vauthors = Geldenhuys WJ, Van der Schyf CJ | title = Serotonin 5-HT6 receptor antagonists for the treatment of Alzheimer's disease | journal = Curr Top Med Chem | volume = 8 | issue = 12 | pages = 1035–1048 | date = 2008 | pmid = 18691131 | doi = 10.2174/156802608785161420 | url = }}{{cite journal | vauthors = Glennon RA, Siripurapu U, Roth BL, Kolanos R, Bondarev ML, Sikazwe D, Lee M, Dukat M | title = The medicinal chemistry of 5-HT6 receptor ligands with a focus on arylsulfonyltryptamine analogs | journal = Curr Top Med Chem | volume = 10 | issue = 5 | pages = 579–595 | date = 2010 | pmid = 20166945 | doi = 10.2174/156802610791111542 | pmc = 5839515 | url = }}{{cite journal | vauthors = Siddiqui N, Andalip, Bawa S, Ali R, Afzal O, Akhtar MJ, Azad B, Kumar R | title = Antidepressant potential of nitrogen-containing heterocyclic moieties: An updated review | journal = J Pharm Bioallied Sci | volume = 3 | issue = 2 | pages = 194–212 | date = April 2011 | pmid = 21687347 | doi = 10.4103/0975-7406.80765 | doi-access = free | pmc = 3103913 | url = }} and dual monoamine releasing agents and serotonin receptor agonists like isoAMT (PAL-569).{{cite thesis | last=Bauer | first=Clayton T. | title=Determinants of Abuse-Related Effects of Monoamine Releasers in Rats | website=VCU Scholars Compass | date=5 July 2014 | doi=10.25772/AN08-SZ65 | url=https://scholarscompass.vcu.edu/etd/522/ | access-date=24 November 2024}}{{cite journal | vauthors = Banks ML, Bauer CT, Blough BE, Rothman RB, Partilla JS, Baumann MH, Negus SS | title = Abuse-related effects of dual dopamine/serotonin releasers with varying potency to release norepinephrine in male rats and rhesus monkeys | journal = Exp Clin Psychopharmacol | volume = 22 | issue = 3 | pages = 274–284 | date = June 2014 | pmid = 24796848 | pmc = 4067459 | doi = 10.1037/a0036595 | url = }}{{cite journal | vauthors = Lyon RA, Titeler M, Seggel MR, Glennon RA | title = Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens | journal = Eur J Pharmacol | volume = 145 | issue = 3 | pages = 291–297 | date = January 1988 | pmid = 3350047 | doi = 10.1016/0014-2999(88)90432-3 | url = }}

JRT is the isotryptamine analogue of LSD and may be considered a cyclized isotryptamine.{{cite journal | vauthors = Tuck JR, Dunlap LE, Khatib YA, Hatzipantelis CJ, Weiser Novak S, Rahn RM, Davis AR, Mosswood A, Vernier AM, Fenton EM, Aarrestad IK, Tombari RJ, Carter SJ, Deane Z, Wang Y, Sheridan A, Gonzalez MA, Avanes AA, Powell NA, Chytil M, Engel S, Fettinger JC, Jenkins AR, Carlezon WA, Nord AS, Kangas BD, Rasmussen K, Liston C, Manor U, Olson DE | title = Molecular design of a therapeutic LSD analogue with reduced hallucinogenic potential | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 122 | issue = 16 | pages = e2416106122 | date = April 2025 | pmid = 40228113 | doi = 10.1073/pnas.2416106122 | doi-access = free | pmc = 12037037 }}{{cite thesis | vauthors = Dunlap L | degree = Ph.D. | publisher = University of California, Davis | chapter=Chapter 5. An Analog of LSD With Antipsychotic Potential | pages=105–114 | title=Development of Non-Hallucinogenic Psychoplastogens | date = 2022 | url=https://escholarship.org/content/qt5qr3w0gm/qt5qr3w0gm.pdf#page=112}}