Chemistry:N-Isopropyltryptamine

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N-Isopropyltryptamine
Clinical data
Other namesNiPT; IPT; N-iP-T
Drug classSerotonin receptor agonist; Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC13H18N2
Molar mass202.301 g·mol−1
3D model (JSmol)

N-Isopropyltryptamine (NiPT) is a serotonin receptor agonist of the tryptamine family.[1][2]

Use and effects

According to Alexander Shulgin, no active dose level of NiPT has yet been found in humans.[1]

Pharmacology

Pharmacodynamics

NiPT 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.[2] The drug is also a weak serotonin reuptake inhibitor.[2]

Chemistry

Analogues

Analogues of NiPT include N-methyltryptamine (NET), N-ethyltryptamine, N-sec-butyltryptamine (NsBT), N-tert-butyltryptamine (NtBT), and diisopropyltryptamine (DiPT), among others.[1]

Derivatives

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][2] 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][2] 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]

Society and culture

Canada

NiPT is not a controlled substance in Canada as of 2025.[8]

See also

References

  1. ↑ 1.0 1.1 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. https://books.google.com/books?id=jl_ik66IumUC. 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." 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berlin) 231 (21): 4135–4144. October 2014. doi:10.1007/s00213-014-3557-7. PMID 24800892. 
  3. ↑ "The hallucinogenic world of tryptamines: an updated review". Archives of Toxicology 89 (8): 1151–1173. August 2015. doi:10.1007/s00204-015-1513-x. PMID 25877327. Bibcode: 2015ArTox..89.1151A. https://psilosybiini.info/paperit/The%20hallucinogenic%20world%20of%20tryptamines,%20an%20updated%20review%20(Ara%FAjo%20et%20al.,%202015).pdf. 
  4. ↑ "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. March 2023. doi:10.1107/S2056989023002098. PMID 37057027. Bibcode: 2023AcCrE..79..280L. 
  5. ↑ 5.0 5.1 5.2 5.3 "Structure-activity relationships of serotonergic 5-MeO-DMT derivatives: insights into psychoactive and thermoregulatory properties". Molecular Psychiatry 29 (8): 2346–2358. August 2024. doi:10.1038/s41380-024-02506-8. PMID 38486047. 
  6. ↑ 6.0 6.1 "Psychedelic-like Activity of Norpsilocin Analogues". ACS Chemical Neuroscience 15 (2): 315–327. January 2024. doi:10.1021/acschemneuro.3c00610. PMID 38189238. 
  7. ↑ 7.0 7.1 7.2 "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. December 2024. doi:10.1021/acschemneuro.4c00513. PMID 39636099. 
  8. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 



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