# Pip-Tryptamine
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> Source: https://en.wikipedia.org/wiki/Pip-Tryptamine
> Source revision: 1356147998
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{{Infobox drug
| drug_name = pip-Tryptamine
| image = Pip-Tryptamine.svg
| image_class = skin-invert-image
| width = 200px
| image2 = pip-T 3D.png
| image_class2 = bg-transparent
| width2 = 225px
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| class = [Serotonin receptor modulator](/source/Serotonin_receptor_modulator)
| ATC_prefix = None
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| CAS_number = 26628-87-5
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| PubChem = 33560
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| DrugBank =
| ChemSpiderID = 30961
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| ChEMBL = 2138465
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| synonyms = 3-(2-Piperidinoethyl)indole; ''N''-Piperidyltryptamine; ''N'',''N''-Piperidyltryptamine; Piperidinyltryptamine; Piperidinotryptamine; PIT; ''N'',''N''-Pentamethylenetryptamine
| IUPAC_name = 3-(2-piperidin-1-ylethyl)-1''H''-indole
| C=15 | H=20 | N=2
| SMILES = C1CCN(CC1)CCC2=CNC3=CC=CC=C32
| StdInChI = 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
| StdInChIKey = 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](/source/serotonin_receptor_modulator) and possible [serotonergic psychedelic](/source/serotonergic_psychedelic) of the [tryptamine](/source/substituted_tryptamine) family.[{{cite book | vauthors = Nichols DE | chapter = Chemistry and Structure–Activity Relationships of Psychedelics | title = Behavioral Neurobiology of Psychedelic Drugs | journal = Current Topics in Behavioral Neurosciences | series = Curr Top Behav Neurosci | volume = 36 | issue = | pages = 1–43 | date = 2018 | pmid = 28401524 | doi = 10.1007/7854_2017_475 | isbn = 978-3-662-55878-2 | url = | quote = 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.}}][{{cite book | author1 = [Alexander T. Shulgin](/source/Alexander_T._Shulgin) | author2 = [Ann Shulgin](/source/Ann_Shulgin) | chapter = #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" | pages = 577–578 | chapter-url = https://erowid.org/library/books_online/tihkal/tihkal52.shtml | title = PiHKAL: A Chemical Love Story | date = 1991 | publisher = Transform Press | edition = 1st | location = Berkeley, CA | isbn = 978-0-9630096-0-9 | oclc = 25627628 | url = https://books.google.com/books?id=O8AdHBGybpcC | quote = 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: [...]}}][{{cite journal | vauthors = McKenna DJ, Repke DB, Lo L, Peroutka SJ | title = Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes | journal = Neuropharmacology | volume = 29 | issue = 3 | pages = 193–198 | date = March 1990 | pmid = 2139186 | doi = 10.1016/0028-3908(90)90001-8 | url = | doi-access = free }}][{{cite journal | vauthors = 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 | title = Four Novel Synthetic Tryptamine Analogs Induce Head-Twitch Responses and Increase 5-HTR2a in the Prefrontal Cortex in Mice | journal = Biomol Ther (Seoul) | volume = 28 | issue = 1 | pages = 83–91 | date = January 2020 | pmid = 31230432 | pmc = 6939696 | doi = 10.4062/biomolther.2019.049 | url = }}][{{cite journal | vauthors = Barlow RB, Khan I | title = Actions of some analogues of tryptamine on the isolated rat uterus and on the isolated rat fundus strip preparations | journal = Br J Pharmacol Chemother | volume = 14 | issue = 1 | pages = 99–107 | date = March 1959 | pmid = 13651585 | pmc = 1481812 | doi = 10.1111/j.1476-5381.1959.tb00934.x | url = }}][{{cite journal | vauthors = Cami-Kobeci G, Slatford PA, Whittlesey MK, Williams JM | title = N-Alkylation of phenethylamine and tryptamine | journal = Bioorg Med Chem Lett | volume = 15 | issue = 3 | pages = 535–537 | date = February 2005 | pmid = 15664808 | doi = 10.1016/j.bmcl.2004.11.050 | url = | quote = 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).}}] It is the [derivative](/source/chemical_derivative) of [tryptamine](/source/tryptamine) in which the [amine](/source/amine) has been [cyclized](/source/cyclic_compound) into a [piperidine](/source/piperidine) [ring](/source/ring_(chemistry)).[{{cite journal | vauthors = Barlow RB, Khan I | title = Actions of some analogues of tryptamine on the isolated rat uterus and on the isolated rat fundus strip preparations | journal = Br J Pharmacol Chemother | volume = 14 | issue = 1 | pages = 99–107 | date = March 1959 | pmid = 13651585 | pmc = 1481812 | doi = 10.1111/j.1476-5381.1959.tb00934.x | url = }}]
The drug produces [hypolocomotion](/source/hypolocomotion) in rodents.