4-HO-NiPT


4-HO-NiPT, also known as 4-hydroxy-N-isopropyltryptamine, is a serotonin receptor modulator and putative psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin. It is an analogue of 4-HO-MiPT and 4-HO-DiPT and a derivative of norpsilocin and 4-HO-NET. The drug has been encountered online as a possible novel designer drug.

Use and effects

4-HO-NiPT was not included nor mentioned in Alexander Shulgin's book TiHKAL.

Interactions

Pharmacology

Pharmacodynamics

4-HO-NiPT shows affinity for serotonin receptors, including for the serotonin 5-HT1D, 5-HT1E, 5-HT2A, 5-HT2B, 5-HT2C, 5-HT6, and 5-HT7 receptors. Conversely, it did not show affinity for the serotonin 5-HT1B or 5-HT5A receptors, whereas the serotonin 5-HT1A receptor was not reported. 4-HO-NiPT is a partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors, with values of 24nM, 188nM, and 963nM, respectively. It was also a weak agonist of other serotonin receptors, including the serotonin 5-HT1B, 5-HT1E, 5-HT1F, and 5-HT7A receptors, but not of the 5-HT1A, 5-HT1D, 5-HT4, 5-HT5A, or 5-HT6 receptors.
In contrast to norpsilocin, but similarly to psilocin and certain other N-monoalkyltryptamines like 4-HO-NET, 4-HO-NPT, 4-HO-NALT, and 4-HO-NBnT, the drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. It showed 30-fold lower potency than psilocin in this action in mice, but produced about the same maximal response. Similarly to 4-HO-NiPT, other N-monoalkyltryptamines were also much less potent than psilocin, in the range of 10- to 26-fold less potent. In addition to the head-twitch response, 4-HO-NiPT produces hypothermia in rodents.
4-HO-NiPT is a known metabolite of 4-AcO-DiPT and presumably also of 4-HO-DiPT.

Chemistry

Synthesis

The chemical synthesis of 4-HO-NiPT has been described.

Analogues

s of 4-HO-NiPT include 4-hydroxytryptamine, 4-HO-MiPT, 4-HO-DiPT, psilocin, norpsilocin, 4-HO-NET, 4-HO-NPT, 4-HO-NALT, and 4-HO-NBnT, among others.

History

4-HO-NiPT was first described in the scientific literature, as a metabolite of 4-AcO-DiPT, in 2022. Subsequently, its synthesis was described in 2023 and its pharmacology was reported in 2024. The drug was reported as a possible novel designer drug online in 2022.