4-HO-NBnT
4-HO-NBnT, also known as 4-hydroxy-N-benzyltryptamine, is a serotonin receptor agonist and putative psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to norpsilocin.
It is a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor. The drug produces psychedelic-like effects in animals.
4-HO-NBnT was first described in the scientific literature in 2024.
Interactions
Pharmacology
Pharmacodynamics
4-HO-NBnT is a potent ligand of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. Of a series of nine N-monoalkyl-4-hydroxytryptamines, it was the most potent agonist of the serotonin 5-HT2A and 5-HT2B receptors. In addition, it was second only to norpsilocin in terms of potency as an agonist of the serotonin 5-HT2C receptor. 4-HO-NBnT acts as a high-efficacy partial agonist of the serotonin 5-HT2A receptor, as a very weak partial agonist or antagonist of the serotonin 5-HT2B receptor, and as a full agonist of the serotonin 5-HT2C receptor. Its and values were 2.9nM at the serotonin 5-HT2A receptor, 4.9nM at the serotonin 5-HT2B receptor, and 70.7nM at the serotonin 5-HT2C receptor.In addition to the serotonin 5-HT2 receptors, 4-HO-NBnT shows affinity for and potent partial agonism of other serotonin receptors, including the serotonin 5-HT1B, 5-HT1D, 5-HT1E, and 5-HT7A receptors. In contrast to norpsilocin and psilocin, 4-HO-NBnT was inactive as a serotonin 5-HT1A receptor agonist. It also shows substantial affinity for sigma σ1 and σ2 receptors.
4-HO-NBnT produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. Its potency in inducing the head-twitch response is about 10-fold lower than that of psilocin, but is of about the same maximal efficacy in terms of frequency of head twitches. The production of the head-twitch response with the drug is in contrast to norpsilocin, which does not cause this response even at very high doses. 4-HO-NBnT also produces hypolocomotion and hypothermia in rodents.