Wikipedia

Isotryptamine

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

Isotryptamine
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
  • 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).

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]

References

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  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 6581313.41-45&rft.date=1984-01&rft_id=info:doi/10.1021/jm00367a008&rft_id=info:pmid/6581313&rft.aulast=Glennon&rft.aufirst=RA&rft.au=Jacyno, JM&rft.au=Young, R&rft.au=McKenney, JD&rft.au=Nelson, D&rfr_id=info:sid/en.wikipedia.org:Isotryptamine" class="Z3988">
  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 31977208.1142-1155&rft.date=2020-02&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7075704#id-name=PMC&rft_id=info:pmid/31977208&rft_id=info:doi/10.1021/acs.jmedchem.9b01404&rft.aulast=Dunlap&rft.aufirst=LE&rft.au=Azinfar, A&rft.au=Ly, C&rft.au=Cameron, LP&rft.au=Viswanathan, J&rft.au=Tombari, RJ&rft.au=Myers-Turnbull, D&rft.au=Taylor, JC&rft.au=Grodzki, AC&rft.au=Lein, PJ&rft.au=Kokel, D&rft.au=Olson, DE&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7075704&rfr_id=info:sid/en.wikipedia.org:Isotryptamine" class="Z3988">
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  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.
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