Pip-Tryptamine

pip-Tryptamine
Clinical data
Other names	3-(2-Piperidinoethyl)indole; N-Piperidyltryptamine; N,N-Piperidyltryptamine; Piperidinyltryptamine; Piperidinotryptamine; PIT; N,N-Pentamethylenetryptamine
Drug class	Serotonin receptor modulator
Identifiers
	IUPAC name 3-(2-piperidin-1-ylethyl)-1H-indole;
CAS Number	26628-87-5;
PubChem CID	33560;
ChemSpider	30961;
ChEMBL	ChEMBL2138465;
CompTox Dashboard (EPA)	DTXSID70181173 ;
Chemical and physical data
Formula	C15H20N2
Molar mass	228.339 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CCN(CC1)CCC2=CNC3=CC=CC=C32;
	InChI InChI=1S/C15H20N2/c1-4-9-17(10-5-1)11-8-13-12-16-15-7-3-2-6-14(13)15/h2-3,6-7,12,16H,1,4-5,8-11H2; Key:PJVCNRSWJSLGCV-UHFFFAOYSA-N;

pip-Tryptamine (pip-T), also known as N,N-pentamethylenetryptamine, N,N-piperidyltryptamine, or 3-(2-piperidinoethyl)indole, is a serotonin receptor modulator and possible serotonergic psychedelic of the tryptamine family. It is the derivative of tryptamine in which the amine has been cyclized into a piperidine ring.

Its affinities (IC₅₀Tooltip half-maximal inhibitory concentration) for serotonin receptors were 600 nM for the serotonin 5-HT_1A receptor, 760 nM for the serotonin 5-HT_2A receptor, and 1,250 nM for the serotonin 5-HT_2B receptor, whereas other serotonin receptors were not reported. The affinity of pip-T for the serotonin 5-HT_2A receptor was about 10-fold lower than that of dimethyltryptamine (DMT) and was about 7-fold lower than that of pyr-tryptamine (pyr-T; N,N-pyrrolidinyltryptamine).

The drug produces hypolocomotion in rodents. In addition, it induces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. This was blocked by the serotonin 5-HT_2A receptor antagonist ketanserin. Hence, the drug may have hallucinogenic effects in humans. Conversely, pip-T did not produce conditioned place preference (CPP) and was not self-administered, suggesting that it lacks reinforcing properties and misuse potential, similarly to most other tryptamines.

Pip-T was first described in the scientific literature by 1959 and was more thoroughly characterized in 1990 and 2020.