4-HO-NBnT

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4-HO-NBnT
Clinical data
Other names4-OH-NBnT; 4-HO-NB-T; 4-Hydroxy-N-benzyltryptamine
Drug classNon-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
FormulaC17H18N2O
Molar mass266.344 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]

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

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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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 EC50Tooltip half-maximal effective concentration and EmaxTooltip 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

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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

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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

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

Analogues

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Chemical structures of 4-HO-NET, 4-HO-NPT, 4-HO-NiPT, and 4-HO-NBnT.[1]

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

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

See also

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References

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  1. ^ a b c d e f g h i j k l m n o p q r s t u v w x 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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