5-MeO-NiPT

5-MeO-NiPT
Clinical data
Other names5-Methoxy-N-isopropyltryptamine
Drug classSerotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
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
FormulaC14H20N2O
Molar mass232.327 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. It was never mentioned in Alexander Shulgin's TiHKAL. The drug was encountered as a novel designer and recreational drug by 2014.

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

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. It also produces hypolocomotion and hypothermia in rodents. In combination with the serotonin 5-HT1A receptor antagonist WAY-100635 however, 5-MeO-NiPT instead produces hyperlocomotion.

5-MeO-NiPT is an active metabolite of 5-MeO-MiPT and 5-MeO-DiPT.

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