5-MeO-NiPT

Last updated
5-MeO-NiPT
MeO-NIPT.svg
Clinical data
Other names5-Methoxy-N-isopropyltryptamine
Drug class Serotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
Identifiers
  • N-[2-(5-methoxy-1H-indol-3-yl)ethyl]propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
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 serotonin receptor agonist and serotonergic psychedelic of the tryptamine family. [1] [2] [3] It has been encountered as a novel designer and recreational drug. [2] [4]

Contents

The drug 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. [3] [2]

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] [5]

See also

References

  1. 1 2 3 4 5 6 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 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 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. Retrieved 2 March 2025.
  5. ↑ 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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