5-Nitrotryptamine

5-Nitrotryptamine
Clinical data
Other names5-Nitro-T; Nitro-I; NitroI; 3-(2-Aminoethyl)-5-nitroindole
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 2-(5-nitro-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H11N3O2
Molar mass205.217 g·mol−1
3D model (JSmol)
  • C1=CC2=C(C=C1[N+](=O)[O-])C(=CN2)CCN
  • InChI=1S/C10H11N3O2/c11-4-3-7-6-12-10-2-1-8(13(14)15)5-9(7)10/h1-2,5-6,12H,3-4,11H2
  • Key:GPZRBKWRRKBOAC-UHFFFAOYSA-N

5-Nitrotryptamine, also known as Nitro-I, is a serotonin receptor modulator and psychedelic drug of the tryptamine family.[1][2] It is the 5-nitro derivative of tryptamine.[1][2]

The drug is a biased agonist of the serotonin 5-HT2A receptor (Ki = 490–2,050 nM; EC50Tooltip half-maximal effective concentration = 0.11–491 nM; EmaxTooltip maximal efficacy = 44–108%).[1][2] It shows high selectivity (10-fold) for activation of the Gαq pathway over β-arrestin2 recruitment and very high selectivity (>50-fold) for activation of the Gαq pathway over the Gαi1 pathway.[1]

Given via intracerebroventricular injection, Nitro-I produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[1] This effect is absent in serotonin 5-HT2A receptor knockout mice.[1] Unlike 5-phenoxytryptamine (OVT2), Nitro-I does not produce serotonin 5-HT2A receptor-mediated long-term memory deficits.[1]

The chemical synthesis of Nitro-I has been described.[3]

Nitro-I was first described in the scientific literature by 1953.[3] Subsequently, it was studied and described in greater detail in 2015[2] and 2024.[1]

See also

References

  1. ^ a b c d e f g h Kossatz E, Diez-Alarcia R, Gaitonde SA, Ramon-Duaso C, Stepniewski TM, Aranda-Garcia D, et al. (May 2024). "G protein-specific mechanisms in the serotonin 5-HT2A receptor regulate psychosis-related effects and memory deficits". Nature Communications. 15 (1) 4307. doi:10.1038/s41467-024-48196-2. PMC 11137019. PMID 38811567.
  2. ^ a b c d Martí-Solano M, Iglesias A, de Fabritiis G, Sanz F, Brea J, Loza MI, et al. (April 2015). "Detection of new biased agonists for the serotonin 5-HT2A receptor: modeling and experimental validation". Molecular Pharmacology. 87 (4): 740–746. doi:10.1124/mol.114.097022. PMID 25661038.
  3. ^ a b Shaw E, Woolley DW (1953). "The Synthesis of Nitro- and Aminoindoles Analogous to Serotonin". Journal of the American Chemical Society. 75 (8): 1877–1881. doi:10.1021/ja01104a029. ISSN 0002-7863. Retrieved 1 March 2026.
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.