4-HO-NBnT

Last updated

4-HO-NBnT
Clinical data
Other names4-OH-NBnT; 4-HO-NB-T; 4-Hydroxy-N-benzyltryptamine
Drug class Non-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 3-[2-(benzylamino)ethyl]-1H-indol-4-ol
PubChem CID
Chemical and physical data
Formula C17H18N2O
Molar mass 266.344 g·mol−1
3D model (JSmol)
  • C1=CC=C(C=C1)CNCCC2=CNC3=C2C(=CC=C3)O
  • InChI=1S/C17H18N2O/c20-16-8-4-7-15-17(16)14(12-19-15)9-10-18-11-13-5-2-1-3-6-13/h1-8,12,18-20H,9-11H2
  • Key:NABQSXPKKZCYEY-UHFFFAOYSA-N

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 (4-HO-NMT). [1]

Contents

It is a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor. [1] The drug produces psychedelic-like effects in animals. [1]

4-HO-NBnT was first described in the scientific literature in 2024. [1]

Interactions

Pharmacology

Pharmacodynamics

4-HO-NBnT is a potent ligand of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. [1] Of a series of nine N-monoalkyl-4-hydroxytryptamines, it was the most potent agonist of the serotonin 5-HT2A and 5-HT2B receptors. [1] In addition, it was second only to norpsilocin in terms of potency as an agonist of the serotonin 5-HT2C receptor. [1] 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. [1] Its EC50 Tooltip half-maximal effective concentration and Emax Tooltip maximal efficacy values were 2.9 nM (73%) at the serotonin 5-HT2A receptor, 4.9 nM (11%) at the serotonin 5-HT2B receptor, and 70.7 nM (91%) at the serotonin 5-HT2C receptor. [1]

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. [1] In contrast to norpsilocin and psilocin, 4-HO-NBnT was inactive as a serotonin 5-HT1A receptor agonist. [1] It also shows substantial affinity for sigma σ1 and σ2 receptors (Ki = 43.3 nM and 249 nM, respectively). [1]

4-HO-NBnT produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. [1] Its potency in inducing the head-twitch response is about 10-fold lower than that of psilocin (4-HO-DMT), but is of about the same maximal efficacy in terms of frequency of head twitches. [1] 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. [1] 4-HO-NBnT also produces hypolocomotion and hypothermia in rodents. [1]

Chemistry

4-HO-NBnT, also known as 4-hydroxy-N-benzyltryptamine, is a substituted tryptamine and 4-hydroxytryptamine derivative. [1] It is the 4-hydroxy derivative of N-benzyltryptamine and is related to the naturally occurrence norpsilocin (4-HO-NMT). [1]

Properties

The calculated log P of 4-HO-NBnT is 2.93. [1] This is far higher than for instance norpsilocin (4-HO-NMT), which had a calculated log P of 0.90. [1]

Synthesis

The chemical synthesis of 4-HO-NBnT has been described. [1]

Analogues

Chemical structures of 4-HO-NET, 4-HO-NPT, 4-HO-NiPT, and 4-HO-NBnT. 4-HO-NET, 4-HO-NPT, 4-HO-NiPT & 4-HO-NBnT structure.png
Chemical structures of 4-HO-NET, 4-HO-NPT, 4-HO-NiPT, and 4-HO-NBnT.

Analogues of 4-HO-NBnT include norpsilocin (4-HO-NMT), 4-HO-NET, 4-HO-NPT, 4-HO-NiPT, 4-HO-NALT, 4-HO-NnBT, 4-HO-NtBT, and 4-HO-NcHT, among others. [1]

History

4-HO-NBnT was first described in the scientific literature by Alexander Sherwood and colleagues in 2024. [1]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 Sherwood AM, Burkhartzmeyer EK, Williamson SE, Baumann MH, Glatfelter GC (January 2024). "Psychedelic-like Activity of Norpsilocin Analogues". ACS Chemical Neuroscience. 15 (2): 315–327. doi:10.1021/acschemneuro.3c00610. PMC   10797613 . PMID   38189238.
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