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pip-Tryptamine

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pip-Tryptamine
Clinical data
Other names3-(2-Piperidinoethyl)indole; N-Piperidyltryptamine; N,N-Piperidyltryptamine; Piperidinyltryptamine; Piperidinotryptamine; PIT; N,N-Pentamethylenetryptamine
Drug classSerotonin receptor modulator
Identifiers
  • 3-(2-piperidin-1-ylethyl)-1H-indole
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC15H20N2
Molar mass228.339 g·mol−1
3D model (JSmol)
  • C1CCN(CC1)CCC2=CNC3=CC=CC=C32
  • InChI=1S/C15H20N2/c1-4-9-17(10-5-1)11-8-13-12-16-15-7-3-2-6-14(13)15/h2-3,6-7,12,16H,1,4-5,8-11H2
  • Key:PJVCNRSWJSLGCV-UHFFFAOYSA-N

pip-Tryptamine (pip-T), also known as N,N-pentamethylenetryptamine, N,N-piperidyltryptamine, or 3-(2-piperidinoethyl)indole, is a serotonin receptor modulator and possible serotonergic psychedelic of the tryptamine family.[1][2][3][4][5][6] It is the derivative of tryptamine in which the amine has been cyclized into a piperidine ring.[1][2][3]

Its affinities (IC50Tooltip half-maximal inhibitory concentration) for serotonin receptors were 600 nM for the serotonin 5-HT1A receptor, 760 nM for the serotonin 5-HT2A receptor, and 1,250 nM for the serotonin 5-HT2B receptor, whereas other serotonin receptors were not reported.[1][3] 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).[3]

The drug produces hypolocomotion in rodents.[4] In addition, it induces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[4] This was blocked by the serotonin 5-HT2A receptor antagonist ketanserin.[4] Hence, the drug may have hallucinogenic effects in humans.[4] 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.[4]

Pip-T was first described in the scientific literature by 1959[5] and was more thoroughly characterized in 1990[1][3] and 2020.[4]

See also

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References

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  1. ^ a b c d Nichols DE (2018). "Chemistry and Structure-Activity Relationships of Psychedelics". Curr Top Behav Neurosci. 36: 1–43. doi:10.1007/7854_2017_475. PMID 28401524. A systematic study of the effect of N-alkylation on tryptamine receptor affinities was reported by McKenna et al. (1990). N-alkylated tryptamines were examined with no ring substituents, a 5-methoxy, or 4-hydroxy group. Highest affinities (4–30 nM) for displacement of [125I]DOI from rat cortical homogenate were observed with N,N-dimethyl, N,N-diethyl, N-methyl-N-isopropyl, and N,N-diisopropyl substituents. An affinity of 39 nM was reported for 4-OH-N,N-di(sec-butyl) tryptamine, but the affinity of 4-OH-N,N-diisobutyltryptamine was only 260 nM. Tethering the dialkyl groups into a heterocyclic ring gave mixed results; N-pyrrolidyl had an affinity similar to N,N-dimethyltryptamine (110 vs. 75 nM, respectively), but the affinity for the N-piperidyl was much lower, at 760 nM.
  2. ^ a b Alexander T. Shulgin; Ann Shulgin (1991). "#52. PYR-T TRYPTAMINE, N,N-TETRAMETHYLENE; INDOLE, 3-[2-(1-PYRROLIDYL)ETHYL]; PYRROLIDINE, 1-[2-(3-INDOLYL)ETHYL]; N,N-TETRAMETHYLENETRYPTAMINE; 1-[2-(1H-INDOL-3-YL)ETHYL]PYRROLIDINE; 1-[2-(1-PYRROLIDYL)ETHYL]INDOLE; "PYRROLIDYLTRYPTAMINE"". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. pp. 577–578. ISBN 978-0-9630096-0-9. OCLC 25627628. EXTENSIONS AND COMMENTARY: First of all, the name pyr-T, which is an abbreviation for "pyrrolidinyltryptamine," is out-and-out wrong. There is just one single nitrogen at the end of the tryptamine chain and it cannot be claimed by both halves of the name. It is intrinsic to the name pyrrolidine as well as to the name tryptamine. This is why the name is in quotation marks. This drug has occasionally been called PT in the popular literature, but choosing to spell it out as pyr-T allows a parallel code to be used with the piperidine and morpholine analogues. These two analogues are both described in the literature. The piperidine material (pip-T) is made via the glyoxylamide (mp 182-183 °C) which is reduced with LAH to the target amine (mp 149-150 °C, HC1 salt 220-221 °C). The morpholine analogue (mor-T) also came to be via the glyoxylamide (mp 187-188 °C) and the reduction to the amine which can be an oil, but which has been reported to have a mp 145- 147 °C. The only trials I know of with either of these is with mor-T which, as the fumarate salt, had no effects at all upon the i.m. injection of a 30 milligram bolus. Actually, this neat trilogy of heterocyclics, the pyrrolidine ring, the piperidine ring, and the morpholine ring, have been the chemist's favorite for many years. Leaf through the "Known Tryptamines" appendix, and see how often you see stretched between the nitrogen substituents the phrases: [...]
  3. ^ a b c d e McKenna DJ, Repke DB, Lo L, Peroutka SJ (March 1990). "Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes". Neuropharmacology. 29 (3): 193–198. doi:10.1016/0028-3908(90)90001-8. PMID 2139186.
  4. ^ a b c d e f g Abiero A, Ryu IS, Botanas CJ, Custodio RJ, Sayson LV, Kim M, Lee HJ, Kim HJ, Seo JW, Cho MC, Lee KW, Yoo SY, Jang CG, Lee YS, Cheong JH (January 2020). "Four Novel Synthetic Tryptamine Analogs Induce Head-Twitch Responses and Increase 5-HTR2a in the Prefrontal Cortex in Mice". Biomol Ther (Seoul). 28 (1): 83–91. doi:10.4062/biomolther.2019.049. PMC 6939696. PMID 31230432.
  5. ^ a b Barlow RB, Khan I (March 1959). "Actions of some analogues of tryptamine on the isolated rat uterus and on the isolated rat fundus strip preparations". Br J Pharmacol Chemother. 14 (1): 99–107. doi:10.1111/j.1476-5381.1959.tb00934.x. PMC 1481812. PMID 13651585.
  6. ^ Cami-Kobeci G, Slatford PA, Whittlesey MK, Williams JM (February 2005). "N-Alkylation of phenethylamine and tryptamine". Bioorg Med Chem Lett. 15 (3): 535–537. doi:10.1016/j.bmcl.2004.11.050. PMID 15664808. We were pleased to find that reaction of tryptamine (12) with the appropriate diol (16, 23 and 24) resulted in good conversion to the corresponding pyrrolidine 25, and piperidine 26, and in reasonable isolated yield into azepane 27 (Scheme 6).
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