Isotryptamine

This article is about the specific substance. For the class of substances, see substituted isotryptamine.

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 studied and described.^{[2][3][4][5][6][7]}

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

See also

• Substituted isotryptamine

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. PMC 12226698. 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.