Pip-Tryptamine
pip-Tryptamine, also known as N,N''-pentamethylenetryptamine, N,N''-piperidyltryptamine, or 3-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.
Use and effects
pip-T was only briefly mentioned by Alexander Shulgin in his book TiHKAL. Its properties and effects were not described.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 and was about 7-fold lower than that of pyr-tryptamine.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 and was not self-administered, suggesting that it lacks reinforcing properties and misuse potential, similarly to most other tryptamines.