N-Isopropyltryptamine

Last updated

N-Isopropyltryptamine
NiPT structure.png
Clinical data
Other namesNiPT; IPT; N-iP-T
Drug class Serotonin receptor agonist [1]
Identifiers
  • N-[2-(1H-indol-3-yl)ethyl]propan-2-amine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C13H18N2
Molar mass 202.301 g·mol−1
3D model (JSmol)
  • CC(C)NCCC1=CNC2=CC=CC=C21
  • InChI=1S/C13H18N2/c1-10(2)14-8-7-11-9-15-13-6-4-3-5-12(11)13/h3-6,9-10,14-15H,7-8H2,1-2H3
  • Key:QOCRVKNKLPEDCZ-UHFFFAOYSA-N

N-Isopropyltryptamine (NiPT) is a serotonin receptor agonist of the tryptamine family. [2] [1] It acts as a potent full agonist of the serotonin 5-HT2A receptor, whereas it is inactive as an agonist of the serotonin 5-HT1A receptor. [1] The drug is also a weak serotonin reuptake inhibitor. [1] According to Alexander Shulgin, no active dose level of NiPT has been found in humans. [2]

Some derivatives of NiPT include 4-HO-NiPT, 5-HO-NiPT, and 5-MeO-NiPT, among others. [3] [4] [5] [6] 5-MeO-NiPT is likewise a serotonin receptor agonist. [7] [5] [1] It is a potent full agonist or high-efficacy partial agonist of the serotonin 5-HT1A, 5-HT2A, 5-HT2B, and 5-HT2C receptors. [7] [5] [1] In contrast to 5-MeO-NMT and 5-MeO-NET, which are inactive in the test, 5-MeO-NiPT induces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, and hence may be hallucinogenic in humans. [7] [5] 4-HO-NiPT is also a serotonin receptor agonist and produces the head-twitch response in rodents as well. [6]

References

  1. 1 2 3 4 5 6 Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology. 231 (21). Berlin: 4135–4144. doi:10.1007/s00213-014-3557-7. PMC   4194234 . PMID   24800892.
  2. 1 2 Alexander T. Shulgin, Ann Shulgin (1997). TiHKAL: The Continuation (1st ed.). Berkeley, CA: Transform Press. ISBN   978-0-9630096-9-2. OCLC   38503252 . Retrieved 30 January 2025. The homologue with only one isopropyl group on the nitrogen, N-isopropyltryptamine or NIPT IPT, has been made according to the same recipe, with the indol-3-yl N-isopropylglyoxalylamide (mp 199–200 °C from methanol) obtained in a 98% yield, and the amine hydrochloride (mp 245–246 °C from benzene/methanol) obtained in a 60% yield. The free base distilled at 130–140 °C at 0.1 mm/Hg to give a fraction that spontaneously crystallized to a very hard solid. MS (in m/z): C4H10N+ 72 (100%); indolemethylene+ 131 (60%), 130 (32%); parent ion 202 (3%). No active level has yet been found in man, to my knowledge.
  3. ↑ Araújo AM, Carvalho F, Bastos ML, Guedes de Pinho P, Carvalho M (August 2015). "The hallucinogenic world of tryptamines: an updated review" (PDF). Archives of Toxicology. 89 (8): 1151–1173. doi:10.1007/s00204-015-1513-x. PMID   25877327.
  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. doi:10.1107/S2056989023002098. PMC   10088304 . PMID   37057027.
  5. 1 2 3 4 Puigseslloses P, Nadal-Gratacós N, Ketsela G, Weiss N, Berzosa X, Estrada-Tejedor R, et al. (August 2024). "Structure-activity relationships of serotonergic 5-MeO-DMT derivatives: insights into psychoactive and thermoregulatory properties". Molecular Psychiatry. 29 (8): 2346–2358. doi:10.1038/s41380-024-02506-8. PMC   11412900 . PMID   38486047.
  6. 1 2 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.
  7. 1 2 3 Glatfelter GC, Clark AA, Cavalco NG, Landavazo A, Partilla JS, Naeem M, et al. (December 2024). "Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice". ACS Chemical Neuroscience. 15 (24): 4458–4477. doi:10.1021/acschemneuro.4c00513. PMID   39636099.
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