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.

Use and effects

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

Pharmacology

Pharmacodynamics

N-Benzyltryptamine shows affinity for the serotonin 5-HT2 receptors. Its affinities were 245nM for the serotonin 5-HT2A receptor, 100nM for the serotonin 5-HT2B receptor, and 186nM for the serotonin 5-HT2C receptor. In terms of activational activities, specifically calcium mobilization, N-benzyltryptamine's values were 162nM at the serotonin 5-HT2A receptor and 50nM at the serotonin 5-HT2C receptor. At the serotonin 5-HT2A receptor, it had higher affinity than tryptamine, but lower activational potency in comparison. In other studies, at the rat serotonin 5-HT2A receptor, N-benzyltryptamine's was 407nM and its 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.

Chemistry

Analogues

Analogues of NbNT include 4-HO-NBnT, 5-MeO-NBnT, 5-MeO-T-NBOMe, 5-MeO-T-NB3OMe, and NEtPhOH-THPI, among others. It is also analogous to N-benzylphenethylamines, for instance 25B-NB, 25I-NBOMe, and benzphetamine.

History

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.