Isotryptamine Explained

Isotryptamine, also known as 2-(1-indolyl)ethylamine, is a chemical compound and positional isomer of tryptamine (2-(3-indolyl)ethylamine).[1]

A variety of isotryptamine derivatives, or substituted isotryptamines, have been developed, including serotonergic psychedelics and psychoplastogens like 6-MeO-isoDMT;[2] [3] non-hallucinogenic psychoplastogens like isoDMT, 5-MeO-isoDMT, and AAZ-A-154 (DLX-001);[4] [5] [6] [7] serotonin 5-HT2C receptor agonists like (S)-5,6-difluoro-isoAMT, Ro60-0175 ((S)-5-fluoro-6-chloro-isoAMT), and PNU-181731;[8] [9] [10] [11] [12] serotonin 5-HT6 receptor modulators;[13] [14] [15] and dual monoamine releasing agents and serotonin receptor agonists like isoAMT (PAL-569).[16] [17] [18]

Notes and References

  1. Web site: 2-(1H-indol-1-yl)ethanamine . PubChem . 14 November 2024.
  2. Glennon RA, Jacyno JM, Young R, McKenney JD, Nelson D . Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines . J Med Chem . 27 . 1 . 41–45 . January 1984 . 6581313 . 10.1021/jm00367a008 .
  3. 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 . Identification of Psychoplastogenic N,N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure-Activity Relationship Studies . J Med Chem . 63 . 3 . 1142–1155 . February 2020 . 31977208 . 10.1021/acs.jmedchem.9b01404 . 7075704 .
  4. Duan W, Cao D, Wang S, Cheng J . Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants . Chem Rev . 124 . 1 . 124–163 . January 2024 . 38033123 . 10.1021/acs.chemrev.3c00375 .
  5. Atiq MA, Baker MR, Voort JL, Vargas MV, Choi DS . Disentangling the acute subjective effects of classic psychedelics from their enduring therapeutic properties . Psychopharmacology (Berl) . May 2024 . 38743110 . 10.1007/s00213-024-06599-5 . free .
  6. Rasmussen K, Chytil M, Agrawal R, Leach P, Gillie D, Mungenast A, Vancutsem P, Engel S, Meyer R, Koenig A, Rus M . 14. Preclinical Pharmacology of DLX-001, a Novel Non-Hallucinogenic Neuroplastogen With the Potential for Treating Neuropsychiatric Diseases . Biological Psychiatry . Elsevier BV . 95 . 10 . 2024 . 0006-3223 . 10.1016/j.biopsych.2024.02.192 . S80.
  7. Rasmussen K, Engel S, Chytil M, Koenig A, Meyer R, Rus M, Olson D, Salinas E . 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 . Neuropsychopharmacology . 48 . Suppl 1 . 211–354 (274–275) . December 2023 . 38040810 . 10729596 . 10.1038/s41386-023-01756-4 . December 1, 2024 .
  8. Chang-Fong J, Addo J, Dukat M, Smith C, Mitchell NA, Herrick-Davis K, Teitler M, Glennon RA . Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors . Bioorg Med Chem Lett . 12 . 2 . 155–158 . January 2002 . 11755343 . 10.1016/s0960-894x(01)00713-2 .
  9. Bishop . Michael J . Nilsson . Björn M . New 5-HT2C receptor agonists . Expert Opinion on Therapeutic Patents . 13 . 11 . 2003 . 1354-3776 . 10.1517/13543776.13.11.1691 . 1691–1705.
  10. Dutton . Alice C. . Barnes . Nicholas M. . Anti-obesity pharmacotherapy: Future perspectives utilising 5-HT2C receptor agonists . Drug Discovery Today: Therapeutic Strategies . 3 . 4 . 2006 . 10.1016/j.ddstr.2006.11.005 . 577–583.
  11. Nilsson BM . 5-Hydroxytryptamine 2C (5-HT2C) receptor agonists as potential antiobesity agents . J Med Chem . 49 . 14 . 4023–4034 . July 2006 . 16821762 . 10.1021/jm058240i .
  12. Lee J, Jung ME, Lee J . 5-HT2C receptor modulators: a patent survey . Expert Opin Ther Pat . 20 . 11 . 1429–1455 . November 2010 . 20849206 . 10.1517/13543776.2010.518956 .
  13. Geldenhuys WJ, Van der Schyf CJ . Serotonin 5-HT6 receptor antagonists for the treatment of Alzheimer's disease . Curr Top Med Chem . 8 . 12 . 1035–1048 . 2008 . 18691131 . 10.2174/156802608785161420 .
  14. Glennon RA, Siripurapu U, Roth BL, Kolanos R, Bondarev ML, Sikazwe D, Lee M, Dukat M . The medicinal chemistry of 5-HT6 receptor ligands with a focus on arylsulfonyltryptamine analogs . Curr Top Med Chem . 10 . 5 . 579–595 . 2010 . 20166945 . 10.2174/156802610791111542 . 5839515 .
  15. Siddiqui N, Andalip, Bawa S, Ali R, Afzal O, Akhtar MJ, Azad B, Kumar R . Antidepressant potential of nitrogen-containing heterocyclic moieties: An updated review . J Pharm Bioallied Sci . 3 . 2 . 194–212 . April 2011 . 21687347 . 10.4103/0975-7406.80765 . free . 3103913 .
  16. Web site: Bauer . Clayton T. . Determinants of Abuse-Related Effects of Monoamine Releasers in Rats . VCU Scholars Compass . 5 July 2014 . 24 November 2024.
  17. Banks ML, Bauer CT, Blough BE, Rothman RB, Partilla JS, Baumann MH, Negus SS . Abuse-related effects of dual dopamine/serotonin releasers with varying potency to release norepinephrine in male rats and rhesus monkeys . Exp Clin Psychopharmacol . 22 . 3 . 274–284 . June 2014 . 24796848 . 4067459 . 10.1037/a0036595 .
  18. Lyon RA, Titeler M, Seggel MR, Glennon RA . Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens . Eur J Pharmacol . 145 . 3 . 291–297 . January 1988 . 3350047 . 10.1016/0014-2999(88)90432-3 .

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Isotryptamine".

Except where otherwise indicated, Everything.Explained.Today is © Copyright 2009-2025, A B Cryer, All Rights Reserved. Cookie policy.