N-Isopropyltryptamine

N-Isopropyltryptamine (NiPT) is a serotonin receptor agonist of the tryptamine family.^[2][1] It acts as a potent full agonist of the serotonin 5-HT_2A receptor, whereas it is inactive as an agonist of the serotonin 5-HT_1A receptor.^[1] The drug is also a weak serotonin reuptake inhibitor.^[1] According to Alexander Shulgin, no active dose level of NiPT has been found in humans.^[2]

N-Isopropyltryptamine

Clinical data
Other names	NiPT; IPT; N-iP-T
Drug class	Serotonin receptor agonist[1]
Identifiers
IUPAC name N-[2-(1H-indol-3-yl)ethyl]propan-2-amine
CAS Number	14121-10-9
PubChem CID	45590
ChemSpider	41480
Chemical and physical data
Formula	C13H18N2
Molar mass	202.301 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)NCCC1=CNC2=CC=CC=C21
InChI InChI=1S/C13H18N2/c1-10(2)14-8-7-11-9-15-13-6-4-3-5-12(11)13/h3-6,9-10,14-15H,7-8H2,1-2H3 Key:QOCRVKNKLPEDCZ-UHFFFAOYSA-N

Some derivatives of NiPT include 4-HO-NiPT, 5-HO-NiPT, and 5-MeO-NiPT, among others.^[3][4][5][6] 5-MeO-NiPT is likewise a serotonin receptor agonist.^[7][5][1] It is a potent full agonist or high-efficacy partial agonist of the serotonin 5-HT_1A, 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors.^[7][5][1] In contrast to 5-MeO-NMT and 5-MeO-NET, which are inactive in the test, 5-MeO-NiPT induces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, and hence may be hallucinogenic in humans.^[7][5] 4-HO-NiPT is also a serotonin receptor agonist and produces the head-twitch response in rodents as well.^[6]