4-HO-NiPT

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4-HO-NiPT
Clinical data
Other names4-Hydroxy-N-isopropyltryptamine; 4-Hydroxy-NiPT; 4-HO-NIPT
Drug classSerotonin 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
FormulaC13H18N2O
Molar mass218.300 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]

Use and effects

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

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-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 EC50Tooltip half-maximal effective concentration (EmaxTooltip maximal efficacy) values of 24 nM (88.4%), 188 nM (69.9%), and 963 nM (45.2%), respectively.[2] It was also a weak agonist of other serotonin receptors, including the serotonin 5-HT1B, 5-HT1E, 5-HT1F, and 5-HT7A receptors (EC50 = 1,400–23,000 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

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Synthesis

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

Analogues

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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

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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

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References

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  1. ^ a b c d 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. ^ a b c d e f g h i j k l m 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. ^ a b "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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