Chemistry:5-MeO-NiPT

From HandWiki

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]

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 nor 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.[5]

Society and culture

Canada

5-MeO-NiPT is not a controlled substance in Canada.[7]

Sweden

5-MeO-NiPT is a controlled substance in Sweden.[8]

United States

5-MeO-NiPT is not an explicitly controlled substance in the United States.[9] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 "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. December 2024. doi:10.1021/acschemneuro.4c00513. PMID 39636099. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 "Structure-activity relationships of serotonergic 5-MeO-DMT derivatives: insights into psychoactive and thermoregulatory properties". Mol Psychiatry 29 (8): 2346–2358. August 2024. doi:10.1038/s41380-024-02506-8. PMID 38486047. 
  3. ↑ 3.0 3.1 3.2 3.3 "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl) 231 (21): 4135–4144. October 2014. doi:10.1007/s00213-014-3557-7. 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. https://op.europa.eu/en/publication-detail/-/publication/2a312ed2-a236-456a-b5a8-930b31442208/language-en. Retrieved 2 March 2025. 
  5. ↑ 5.0 5.1 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml. 
  6. ↑ "The hallucinogenic world of tryptamines: an updated review". Archives of Toxicology 89 (8): 1151–1173. 2015. doi:10.1007/s00204-015-1513-x. ISSN 0340-5761. 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. 
  7. ↑ "Controlled Drugs and Substances Act". 5 December 2025. https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  8. ↑ "5-MeO-NIPT" (in ru). https://aipsin.com/newsubstance/154/. 
  9. ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026, https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf 



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