5-MeO-pip-T
5-MeO-pip-T, also known as 5-methoxy-pip-tryptamine, is a serotonin receptor modulator and selective serotonin 5-HT1A 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, 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.
Pharmacology
Pharmacodynamics
5-MeO-pip-T shows affinity for the serotonin 5-HT2A receptor but not for the serotonin 5-HT2C receptor. It has been found to act as a low-potency and low-efficacy agonist of the serotonin 5-HT2A receptor and the serotonin 5-HT4 receptor. These findings were also replicated in a subsequent study, where 5-MeO-pip-T showed far lower potency and efficacy as a serotonin 5-HT2A 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-HT1A 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-HT1A receptor agonist.
Chemistry
Synthesis
The chemical synthesis of 5-MeO-pip-T has been described.
Analogues
Analogues of 5-MeO-pip-T include pip-tryptamine, pyr-tryptamine, 5-MeO-pyr-T, 5-MeO-DMT, and 5-MeO-DET, among others.
5-MeO-mor-T
5-MeO-mor-T, the 5-methoxy derivative of mor-tryptamine 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, but he did not test it.
History
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. The pharmacology of 5-MeO-pip-T was described in greater detail in 2024.