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]
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| Other names | 5-Nitro-T; Nitro-I; NitroI; 3-(2-Aminoethyl)-5-nitroindole |
| Drug class | Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen |
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| Formula | C10H11N3O2 |
| Molar mass | 205.217 g·mol−1 |
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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
editReferences
edit- 1 2 3 4 5 6 7 8 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.
- 1 2 3 4 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.
- 1 2 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.