N-Benzyltryptamine

N-Benzyltryptamine, also known as T-NB, NB-T, or NBnT, is a serotonin receptor modulator of the tryptamine family. It is the N-benzyl derivative of tryptamine.

N-Benzyltryptamine is not known to have been tested in humans, and it is unknown whether it may produce hallucinogenic effects in humans.

N-Benzyltryptamine shows affinity for the serotonin 5-HT₂ receptors. Its affinities (K_i) were 245 nM for the serotonin 5-HT_2A receptor, 100 nM for the serotonin 5-HT_2B receptor, and 186 nM for the serotonin 5-HT_2C receptor. In terms of activational activities, specifically calcium mobilization, N-benzyltryptamine's EC₅₀Tooltip half-maximal effective concentration (E_maxTooltip maximal efficacy) values were 162 nM (62%) at the serotonin 5-HT_2A receptor and 50 nM (121%) at the serotonin 5-HT_2C receptor. At the serotonin 5-HT_2A receptor, it had higher affinity than tryptamine, but lower activational potency in comparison. In other studies, at the rat serotonin 5-HT_2A receptor, N-benzyltryptamine's EC₅₀ was 407 nM and its E_max was 26%.

The drug has been reported to produce serotonergic psychedelic-like effects in early studies in animals. This included hyperthermia and behavioral changes in the open field test.

Analogues of NbNT include 4-HO-NBnT, 5-MeO-NBnT, 5-MeO-T-NBOMe, and NEtPhOH-THPI, among others. It is also analogous to N-benzylphenethylamines, for instance 25B-NB (N-benzyl-2C-B), 25I-NBOMe, and benzphetamine (N-benzylmethamphetamine).

N-Benzyltryptamine was first described in the scientific literature by Roger W. Brimblecombe and colleagues by at least 1964. Derivatives of N-benzyltryptamine, such as 5-MeO-T-NBOMe, have subsequently been described as well.