pip-Tryptamine (pip-T), also known as N,N-pentamethylenetryptamine, N,N-piperidyltryptamine, or 3-(2-piperidinoethyl)indole (PEI), 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.
Use and effects pip-T was only briefly mentioned by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved). Its properties and effects were not described.
Interactions
Pharmacology Pharmacodynamics The affinities () of pip-tryptamine for serotonin receptors were 600nM for the serotonin 5-HT1A receptor, 760nM for the serotonin 5-HT2A receptor, and 1,250nM for the serotonin 5-HT2B receptor, whereas other serotonin receptors were not reported. The affinity of pip-T for the serotonin 5-HT2A 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). Pip-T is a serotonin receptor agonist in the rat uterus with similar potency as DMT, but showed 20-fold lower potency than DMT in the rat fundus strip.
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-HT2A 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.
Chemistry Synthesis The chemical synthesis of pip-T has been described.
Analogues Analogues of pip-T include 5-MeO-pip-T, 10,11-secoergoline (α,N-Pip-T), pyr-T, MPMI, SN-22, RU-24,969, EMD-386088, and AHR-1709, among others.
mor-Tryptamine
mor-Tryptamine, or mor-T, also known as 3-(2-morpholinoethyl)indole (MEI), is the analogue of pip-T with the piperidine ring replaced with a morpholine ring. It was briefly described by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved), including its chemical synthesis. The drug was tested by intramuscular injection of 30mg as the fumarate salt, but produced no effects whatsoever. Accordingly, mor-T was completely inactive as a serotonin receptor agonist in the rat uterus and rat stomach strip. It has also been assessed in other serotonin receptor assays, where it showed mixed activities.Taylor, E. W. (1985). The Development of Indoleamine Derivatives Selective for Subtypes of Serotonin Receptors (TRYPTAMINE, BASILAR ARTERY, ANTAGONIST, ERGOLINE, SYNTHESIS). The University of Arizona. http://hdl.handle.net/10150/188104 The 5-methoxy derivative of mor-T, 5-MeO-mor-T, is also known, but is not known to have been tested.
History Pip-T was first described in the scientific literature by 1959 and was more thoroughly characterized in 1990 and 2020.
See also Substituted tryptamine Cyclized tryptamine
References
External links pip-T - Isomer Design