5-MeO-NiPT

Last updated
5-MeO-NiPT
5-MeO-NIPT.svg
Clinical data
Other names5-Methoxy-N-isopropyltryptamine
Drug class Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • N-[2-(5-methoxy-1H-indol-3-yl)ethyl]propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C14H20N2O
Molar mass 232.327 g·mol−1
3D model (JSmol)
  • COc1ccc2c(c1)c(CCNC(C)C)c[nH]2
  • InChI=1S/C14H20N2O/c1-10(2)15-7-6-11-9-16-14-5-4-12(17-3)8-13(11)14/h4-5,8-10,15-16H,6-7H2,1-3H3
  • Key:QQZJNZJNPDORBO-UHFFFAOYSA-N

5-MeO-NiPT, also known as 5-methoxy-N-isopropyltryptamine, is a psychedelic drug of the tryptamine family related to 5-MeO-DMT. [1] [2] [3]

Contents

The drug acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor. [1] [2] [3]

5-MeO-NiPT was encountered as a novel designer and recreational drug by 2014. [2] [4]

Use and effects

5-MeO-NiPT was not included or mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved). [5]

Interactions

Pharmacology

Pharmacodynamics

5-MeO-NiPT is a full agonist or near-full agonist of the serotonin 5-HT1A, 5-HT2A, 5-HT2B, and 5-HT2C receptors. [1] [2] [3] It is inactive as a serotonin releasing agent and is very weak as a serotonin reuptake inhibitor. [2] [3]

Unlike most other N-monoalkylated tryptamines, 5-MeO-NiPT produces the head-twitch response (HTR), a behavioral proxy of psychedelic effects, in rodents, albeit relatively weakly. [1] [2] It also produces hypolocomotion and hypothermia in rodents. [1] [2] In combination with the serotonin 5-HT1A receptor antagonist WAY-100635 however, 5-MeO-NiPT instead produces hyperlocomotion. [1]

5-MeO-NiPT is an active metabolite of 5-MeO-MiPT and 5-MeO-DiPT. [1] [6]

Chemistry

Analogues

Analogues of 5-MeO-NiPT include N-isopropyltryptamine (NiPT), 5-MeO-NMT, 5-MeO-NET, 5-MeO-DiPT, and 5-MeO-MiPT, among others.

See also

References

  1. 1 2 3 4 5 6 7 Glatfelter GC, Clark AA, Cavalco NG, Landavazo A, Partilla JS, Naeem M, Golen JA, Chadeayne AR, Manke DR, Blough BE, McCorvy JD, Baumann MH (December 2024). "Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice". ACS Chem Neurosci. 15 (24): 4458–4477. doi:10.1021/acschemneuro.4c00513. PMID   39636099.
  2. 1 2 3 4 5 6 7 Puigseslloses P, Nadal-Gratacós N, Ketsela G, Weiss N, Berzosa X, Estrada-Tejedor R, Islam MN, Holy M, Niello M, Pubill D, Camarasa J, Escubedo E, Sitte HH, López-Arnau R (August 2024). "Structure-activity relationships of serotonergic 5-MeO-DMT derivatives: insights into psychoactive and thermoregulatory properties". Mol Psychiatry. 29 (8): 2346–2358. doi:10.1038/s41380-024-02506-8. PMC   11412900 . PMID   38486047.
  3. 1 2 3 4 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 (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC   4194234 . PMID   24800892.
  4. ↑ EMCDDA–Europol 2014 annual report on the implementation of Council Decision 2005/387/JHA. Publications Office of the European Union. 3 July 2015. ISBN   978-92-9168-821-0 . Retrieved 2 March 2025.
  5. ↑ Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  6. ↑ Araújo AM, Carvalho F, Bastos ML, Guedes de Pinho P, Carvalho M (2015). "The hallucinogenic world of tryptamines: an updated review" (PDF). Archives of Toxicology. 89 (8): 1151–1173. Bibcode:2015ArTox..89.1151A. doi:10.1007/s00204-015-1513-x. ISSN   0340-5761. PMID   25877327.
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