Chemistry:5-Nitrotryptamine

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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; EC50 = 0.11–491 nM; Emax = 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. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 "G protein-specific mechanisms in the serotonin 5-HT2A receptor regulate psychosis-related effects and memory deficits". Nature Communications 15 (1). May 2024. doi:10.1038/s41467-024-48196-2. PMID 38811567. 
  2. ↑ 2.0 2.1 2.2 2.3 "Detection of new biased agonists for the serotonin 5-HT2A receptor: modeling and experimental validation". Molecular Pharmacology 87 (4): 740–746. April 2015. doi:10.1124/mol.114.097022. PMID 25661038. 
  3. ↑ 3.0 3.1 "The Synthesis of Nitro- and Aminoindoles Analogous to Serotonin". Journal of the American Chemical Society 75 (8): 1877–1881. 1953. doi:10.1021/ja01104a029. ISSN 0002-7863. https://pubs.acs.org/doi/abs/10.1021/ja01104a029. Retrieved 1 March 2026. 



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