5-MeO-pip-T, also known as 5-methoxy-pip-tryptamine, is a serotonin receptor modulator and selective serotonin 5-HT<sub>1A</sub> receptor agonist of the tryptamine family related to 5-MeO-pyr-T.
5-MeO-pip-T was described and partially synthesized by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved), but he did not test it or define its properties or effects. According to Shulgin, he was not in a hurry to test it owing to the unfavorable effects of the structurally related 5-MeO-pyr-T.
5-MeO-pip-T shows affinity for the serotonin 5-HT<sub>2A</sub> receptor (K<sub>i</sub> = 160âÂÂ230nM) but not for the serotonin 5-HT<sub>2C</sub> receptor (K<sub>i</sub> = >10,000nM). It has been found to act as a low-potency and low-efficacy agonist of the serotonin 5-HT<sub>2A</sub> receptor ( = 7,410nM; = 16%) and the serotonin 5-HT<sub>4</sub> receptor ( = 1,200nM; = 34%). These findings were also replicated in a subsequent study, where 5-MeO-pip-T showed far lower potency and efficacy as a serotonin 5-HT<sub>2A</sub> receptor agonist than 5-MeO-DMT or 5-MeO-pyr-T. On the other hand, 5-MeO-pip-T was a potent full agonist of the serotonin 5-HT<sub>1A</sub> receptor, with an of 88.5nM, although it was 42-fold less potent in this action than the highly potent 5-MeO-pyr-T. As such, 5-MeO-pip-T was described as a selective serotonin 5-HT<sub>1A</sub> receptor agonist.
The chemical synthesis of 5-MeO-pip-T has been described.
Analogues of 5-MeO-pip-T include pip-tryptamine (pip-T), pyr-tryptamine (pyr-T), 5-MeO-pyr-T, 5-MeO-DMT, and 5-MeO-DET, among others.
5-MeO-mor-T, the 5-methoxy derivative of mor-tryptamine (mor-T) and the analogue of 5-MeO-pip-T in which the piperidine ring is replaced by a morpholine ring, was also partially synthesized and briefly described by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved), but he did not test it.
5-MeO-pip-T was first described in the scientific literature by Richard Glennon and colleagues by 1994. It was briefly described by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved). The pharmacology of 5-MeO-pip-T was described in greater detail in 2024.