5-MeO-NiPT

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 was never mentioned in Alexander Shulgin's TiHKAL.^[4] The drug was encountered as a novel designer and recreational drug by 2014.^[2][5]

5-MeO-NiPT

Clinical data
Other names	5-Methoxy-N-isopropyltryptamine
Drug class	Serotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
Identifiers
IUPAC name N-[2-(5-methoxy-1H-indol-3-yl)ethyl]propan-2-amine
CAS Number	109921-55-3
PubChem CID	707167
ChemSpider	616592
UNII	CEP4J0P21U
CompTox Dashboard (EPA)	DTXSID00351701
Chemical and physical data
Formula	C14H20N2O
Molar mass	232.327 g·mol−1
3D model (JSmol)	Interactive image
SMILES COc1ccc2c(c1)c(CCNC(C)C)c[nH]2
InChI 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

It is a full agonist or near-full agonist of the serotonin 5-HT_1A, 5-HT_2A, 5-HT_2B, and 5-HT_2C 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-HT_1A 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]

See also

• N-Isopropyltryptamine (NiPT)
• 5-MeO-NMT
• 5-MeO-NET