5-Nitrotryptamine
Pharmaceutical compound
From Wikipedia, the free encyclopedia
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]