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. "With both pyr-T and 4-HO-pyr-T, there are two additional ring analogies that are natural companions to 5-MeO-pyr-T. These are the piperidine and the morpholine counterparts, 5-MeO-mor-T and 5-MeO-pip-T. Both compounds are in the literature, and an entry reference to them can be gotten from the “known tryptamines” appendix. [...] With the rather unexpected, and unencouraging descriptions of the pyrrolidine tryptamines in general, and this one in particular, I was not too blinding a hurry to explore the two heterocyclic analogues. The amides are still on the shelf in the lab. If some good reason comes forth to assay the final amines, they can be made with a dash of lithium aluminum hydride, but until then I have other things to do."
Use and effects 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.
Pharmacology Pharmacodynamics 5-MeO-pip-T shows affinity for the serotonin 5-HT2A receptor (Ki = 160–230nM) but not for the serotonin 5-HT2C receptor (Ki = >10,000nM). It has been found to act as a low-potency and low-efficacy agonist of the serotonin 5-HT2A receptor ( = 7,410nM; = 16%) and the serotonin 5-HT4 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-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 (pip-T), pyr-tryptamine (pyr-T), 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 (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.
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 (Tryptamines I Have Known and Loved). The pharmacology of 5-MeO-pip-T was described in greater detail in 2024.
See also Piperidinylethylindole Cyclized tryptamine
References
External links 5-MeO-pip-T - Isomer Design