Isotryptamine

Isotryptamine

Names
IUPAC name 2-indol-1-ylethanamine
Other names 2-Indolylethylamine; 2-(1-Indolyl)ethylamine; 2-(1H-Indol-1-yl)ethanamine
Identifiers
CAS Number	13708-58-2
3D model (JSmol)	Interactive image
ChemSpider	227015
PubChem CID	258690
CompTox Dashboard (EPA)	DTXSID10293224
InChI 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
SMILES C1=CC=C2C(=C1)C=CN2CCN
Properties
Chemical formula	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). Infobox references

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-HT_2C 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.