Isotryptamine

Last updated
Isotryptamine
Isotryptamine.svg
Names
IUPAC name
2-indol-1-ylethanamine
Other names
2-Indolylethylamine; 2-(1-Indolyl)ethylamine; 2-(1H-Indol-1-yl)ethanamine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C10H12N2/c11-6-8-12-7-5-9-3-1-2-4-10(9)12/h1-5,7H,6,8,11H2
    Key: BXEFQUSYBZYTAE-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C=CN2CCN
Properties
C10H12N2
Molar mass 160.220 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 zalsupindole (DLX-001; AAZ-A-154); [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]

References

  1. ↑ "2-(1H-indol-1-yl)ethanamine". PubChem. Retrieved 14 November 2024.
  2. ↑ Glennon RA, Jacyno JM, Young R, McKenney JD, Nelson D (January 1984). "Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines". J Med Chem. 27 (1): 41–45. doi:10.1021/jm00367a008. PMID   6581313.
  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 (February 2020). "Identification of Psychoplastogenic N,N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure-Activity Relationship Studies". J Med Chem. 63 (3): 1142–1155. doi:10.1021/acs.jmedchem.9b01404. PMC   7075704 . PMID   31977208.
  4. ↑ Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chem Rev. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID   38033123.
  5. ↑ Atiq MA, Baker MR, Voort JL, Vargas MV, Choi DS (May 2024). "Disentangling the acute subjective effects of classic psychedelics from their enduring therapeutic properties". Psychopharmacology (Berl). doi: 10.1007/s00213-024-06599-5 . PMID   38743110.
  6. ↑ Rasmussen K, Chytil M, Agrawal R, Leach P, Gillie D, Mungenast A, Vancutsem P, Engel S, Meyer R, Koenig A, Rus M (2024). "14. Preclinical Pharmacology of DLX-001, a Novel Non-Hallucinogenic Neuroplastogen With the Potential for Treating Neuropsychiatric Diseases". Biological Psychiatry. 95 (10). Elsevier BV: S80. doi:10.1016/j.biopsych.2024.02.192. ISSN   0006-3223.
  7. ↑ Rasmussen K, Engel S, Chytil M, Koenig A, Meyer R, Rus M, Olson D, Salinas E (December 2023). "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). doi:10.1038/s41386-023-01756-4. PMC   10729596 . PMID   38040810.
  8. ↑ Chang-Fong J, Addo J, Dukat M, Smith C, Mitchell NA, Herrick-Davis K, Teitler M, Glennon RA (January 2002). "Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors". Bioorg Med Chem Lett. 12 (2): 155–158. doi:10.1016/s0960-894x(01)00713-2. PMID   11755343.
  9. ↑ Bishop, Michael J; Nilsson, Björn M (2003). "New 5-HT2C receptor agonists". Expert Opinion on Therapeutic Patents. 13 (11): 1691–1705. doi:10.1517/13543776.13.11.1691. ISSN   1354-3776.
  10. ↑ Dutton, Alice C.; Barnes, Nicholas M. (2006). "Anti-obesity pharmacotherapy: Future perspectives utilising 5-HT2C receptor agonists". Drug Discovery Today: Therapeutic Strategies. 3 (4): 577–583. doi:10.1016/j.ddstr.2006.11.005.
  11. ↑ Nilsson BM (July 2006). "5-Hydroxytryptamine 2C (5-HT2C) receptor agonists as potential antiobesity agents". J Med Chem. 49 (14): 4023–4034. doi:10.1021/jm058240i. PMID   16821762.
  12. ↑ Lee J, Jung ME, Lee J (November 2010). "5-HT2C receptor modulators: a patent survey". Expert Opin Ther Pat. 20 (11): 1429–1455. doi:10.1517/13543776.2010.518956. PMID   20849206.
  13. ↑ Geldenhuys WJ, Van der Schyf CJ (2008). "Serotonin 5-HT6 receptor antagonists for the treatment of Alzheimer's disease". Curr Top Med Chem. 8 (12): 1035–1048. doi:10.2174/156802608785161420. PMID   18691131.
  14. ↑ Glennon RA, Siripurapu U, Roth BL, Kolanos R, Bondarev ML, Sikazwe D, Lee M, Dukat M (2010). "The medicinal chemistry of 5-HT6 receptor ligands with a focus on arylsulfonyltryptamine analogs". Curr Top Med Chem. 10 (5): 579–595. doi:10.2174/156802610791111542. PMC   5839515 . PMID   20166945.
  15. ↑ Siddiqui N, Andalip, Bawa S, Ali R, Afzal O, Akhtar MJ, Azad B, Kumar R (April 2011). "Antidepressant potential of nitrogen-containing heterocyclic moieties: An updated review". J Pharm Bioallied Sci. 3 (2): 194–212. doi: 10.4103/0975-7406.80765 . PMC   3103913 . PMID   21687347.
  16. ↑ Bauer, Clayton T. (5 July 2014). Determinants of Abuse-Related Effects of Monoamine Releasers in Rats. VCU Scholars Compass (Thesis). doi:10.25772/AN08-SZ65 . Retrieved 24 November 2024.
  17. ↑ Banks ML, Bauer CT, Blough BE, Rothman RB, Partilla JS, Baumann MH, Negus SS (June 2014). "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. doi:10.1037/a0036595. PMC   4067459 . PMID   24796848.
  18. ↑ Lyon RA, Titeler M, Seggel MR, Glennon RA (January 1988). "Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens". Eur J Pharmacol. 145 (3): 291–297. doi:10.1016/0014-2999(88)90432-3. PMID   3350047.


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