4-HO-NiPT

Last updated

4-HO-NiPT
Clinical data
Other names4-Hydroxy-N-isopropyltryptamine; 4-Hydroxy-NiPT; 4-HO-NIPT
Drug class Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 3-[2-(propan-2-ylamino)ethyl]-1H-indol-4-ol
PubChem CID
Chemical and physical data
Formula C13H18N2O
Molar mass 218.300 g·mol−1
3D model (JSmol)
  • CC(C)NCCC1=CNC2=C1C(=CC=C2)O
  • InChI=1S/C13H18N2O/c1-9(2)14-7-6-10-8-15-11-4-3-5-12(16)13(10)11/h3-5,8-9,14-16H,6-7H2,1-2H3
  • Key:YJBOZZRZZJEXDB-UHFFFAOYSA-N

4-HO-NiPT, also known as 4-hydroxy-N-isopropyltryptamine, is a serotonin receptor modulator and putative psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). [1] [2] [3] It is an analogue of 4-HO-MiPT (miprocin) and 4-HO-DiPT (iprocin) and a derivative of norpsilocin (4-HO-NMT) and 4-HO-NET. [2] The drug has been encountered online as a possible novel designer drug. [4]

Contents

Use and effects

4-HO-NiPT was not included nor mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved). [5]

Interactions

Pharmacology

Pharmacodynamics

4-HO-NiPT shows affinity for serotonin receptors, including for the serotonin 5-HT1D, 5-HT1E, 5-HT2A, 5-HT2B, 5-HT2C, 5-HT6, and 5-HT7 receptors (Ki = 229–2,461 nM). [2] Conversely, it did not show affinity for the serotonin 5-HT1B or 5-HT5A receptors, whereas the serotonin 5-HT1A receptor was not reported. [2] 4-HO-NiPT is a partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors, with EC50 Tooltip half-maximal effective concentration (Emax Tooltip maximal efficacy) values of 24 nM (88.4%), 188 nM (69.9%), and 963 nM (45.2%), respectively. [2] It was also an agonist of other serotonin receptors, including the serotonin 5-HT1B, 5-HT1E, 5-HT1F, and 5-HT7A receptors (EC50 = 1.4–23 nM, Emax = 20.4–123%), but not of the 5-HT1A, 5-HT1D, 5-HT4, 5-HT5A, or 5-HT6 receptors. [2]

In contrast to norpsilocin, but similarly to psilocin and certain other N-monoalkyltryptamines like 4-HO-NET, 4-HO-NPT, 4-HO-NALT, and 4-HO-NBnT, the drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. [2] It showed 30-fold lower potency than psilocin in this action in mice, but produced about the same maximal response. [2] Similarly to 4-HO-NiPT, other N-monoalkyltryptamines were also much less potent than psilocin, in the range of 10- to 26-fold less potent. [2] In addition to the head-twitch response, 4-HO-NiPT produces hypothermia in rodents. [2]

4-HO-NiPT is a known metabolite of 4-AcO-DiPT and presumably also of 4-HO-DiPT. [1]

Chemistry

Synthesis

The chemical synthesis of 4-HO-NiPT has been described. [1] [2]

Analogues

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
4-HO-NET, 4-HO-NPT, 4-HO-NiPT, and 4-HO-NBnT.

Analogues of 4-HO-NiPT include 4-hydroxytryptamine (4-HT or 4-HO-T), 4-HO-MiPT (miprocin), 4-HO-DiPT (diprocin), psilocin (4-HO-DMT), norpsilocin (4-HO-NMT), 4-HO-NET, 4-HO-NPT, 4-HO-NALT, and 4-HO-NBnT, among others. [2]

History

4-HO-NiPT was first described in the scientific literature, as a metabolite of 4-AcO-DiPT, in 2022. [6] Subsequently, its synthesis was described in 2023 [1] and its pharmacology was reported in 2024. [2] The drug was reported as a possible novel designer drug online in 2022. [4]

See also

References

  1. 1 2 3 4 Laban U, Naeem M, Chadeayne AR, Golen JA, Manke DR (March 2023). "Synthesis and structure of 4-hy-droxy-N-iso-propyl-tryptamine (4-HO-NiPT) and its precursors". Acta Crystallographica. Section e, Crystallographic Communications. 79 (Pt 4): 280–286. Bibcode:2023AcCrE..79..280L. doi:10.1107/S2056989023002098. PMC   10088304 . PMID   37057027.
  2. 1 2 3 4 5 6 7 8 9 10 11 12 13 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.
  3. ↑ Naeem M, Manke DR, Neto CA, Chadeayne AR (2024). Synthetic & structural investigations of novel metal-chelate complexes and tryptamine derivatives: a dissertation in Chemistry and Biochemistry (Doctor of Philosophy thesis). University of Massachusetts Dartmouth. doi:10.62791/2002 . Retrieved 23 November 2025.
  4. 1 2 "4-HO-NIPT (4-hydroxy NiPT)". АИПСИН (in Russian). Retrieved 23 November 2025.
  5. ↑ Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  6. ↑ Malaca S, Huestis MA, Lattanzio L, Marsella LT, Tagliabracci A, Carlier J, et al. (July 2022). "Human Hepatocyte 4-Acetoxy-N,N-Diisopropyltryptamine Metabolite Profiling by Reversed-Phase Liquid Chromatography Coupled with High-Resolution Tandem Mass Spectrometry". Metabolites. 12 (8): 705. doi: 10.3390/metabo12080705 . PMC   9413566 . PMID   36005577.
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