pyr-T

In his 1997 book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin reported neither the dose range nor the duration of the drug.{{cite book | vauthors = Shulgin A, Shulgin A | title = TiHKAL, The Continuation | location = Berkeley, CA, USA | pages = 577–578 | date = 1997 | publisher = Transform Press | isbn = 978-0-9630096-9-2 | edition = 1st | url = https://erowid.org/library/books_online/tihkal/tihkal52.shtml | access-date = 7 April 2018 | ref = HardcopyTiHKAL }}{{cite journal | vauthors = Krasowski MD, Ekins S | title = Using cheminformatics to predict cross reactivity of "designer drugs" to their currently available immunoassays | journal = Journal of Cheminformatics | volume = 6 | pages = 22 | date = 2014 | pmid = 24851137 | pmc = 4029917 | doi = 10.1186/1758-2946-6-22 | doi-access = free }} However, individual experiments employed 25 to 50{{nbsp}}mg orally and 70{{nbsp}}mg smoked. Pyr-T produced effects including malaise, feeling sick, unpleasantness, salivation, muscle and joint pains, dizziness, feeling high, and uncomfortableness. Hallucinogenic effects, for instance visuals, were either absent or minor.

Pyr-T has been found to show affinity for serotonin receptors, including the serotonin 5-HT_1A, 5-HT_2A and 5-HT_2C receptors.{{cite book | vauthors = Nichols DE | chapter = Chemistry and Structure-Activity Relationships of Psychedelics | title = Current Topics in Behavioral Neurosciences | volume = 36 | pages = 1–43 | date = 2018 | pmid = 28401524 | doi = 10.1007/7854_2017_475 | isbn = 978-3-662-55878-2 | url = https://bitnest.netfirms.com/external/10.1007/7854_2017_475 | quote = 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 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 = }} Its affinities ({{Abbrlink|IC₅₀|half-maximal inhibitory concentration}}) for these receptors were 30{{nbsp}}nM for the serotonin 5-HT_1A receptor, 110{{nbsp}}nM for the 5-HT_2A receptor, and 750{{nbsp}}nM for the serotonin 5-HT_2B receptor. The affinities of pyr-T for the serotonin 5-HT_2A and 5-HT_2B receptors were similar to but slightly lower than those of dimethyltryptamine (DMT), whereas its affinity for the serotonin 5-HT_1A receptor was 5.7-fold higher than that of DMT and was intermediate between those of DMT and 5-MeO-DMT. The serotonin 5-HT_1A to 5-HT_2A receptor affinity ratios in the study were about 0.27 for pyr-T, 0.5 for 5-MeO-DMT, 1.4 for bufotenin, 2.3 for DMT, and 32 for psilocin.

Pyr-T has been found to produce behavioral changes in animal tests.{{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 = }} It was described as being as potent as diethyltryptamine (DET) in rodents, cats, and primates, but that it also had a poor margin of activity relative to toxicity and was unlikely to be tested in humans. It has been found to produce hypolocomotion in rodents. Conversely, pyr-T (3{{nbsp}}mg/kg) failed to acutely produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.

{{See also|Substituted tryptamine}}

Pyr-T is a substituted tryptamine in which the amine moiety has been replaced with a pyrrolidine ring. It can be thought of as a cyclized derivative of diethyltryptamine (DET) in which the N,N-ethyl groups have been connected to form the pyrrolidine ring present in pyr-T.

Derivatives of pyr-T include 4-HO-pyr-T, 5-MeO-pyr-T, and 4-F-5-MeO-pyr-T. Analogues of pyr-T include pip-tryptamine, 10,11-secoergoline (α,N-Pip-T), MPMI, and SN-22, among others.

Pyr-T was first characterized by Mitzal by 1962.{{cite journal | vauthors = Mitzal S | title = N/A | journal = Dissertationes Pharm | volume = 14 | pages = 305 | date = 1962 }} Animal toxicity testing was later performed by Hunt and Brimblecombe by 1967.{{cite journal | vauthors = Hunt RR, Brimblecombe RW | title = Synthesis and Biological Activity of Some Ring-Substituted Tryptamines | journal = Journal of Medicinal Chemistry | volume = 10 | issue = 4 | pages = 646–648 | date = July 1967 | pmid = 4962512 | doi = 10.1021/jm00316a027 | ref = Hunt }} The effects of pyr-T in humans were described by Alexander Shulgin in his book TiHKAL in 1997.

{{Reflist}}

• [https://isomerdesign.com/pihkal/explore/5052 Pyr-T - Isomer Design]
• [https://erowid.org/library/books_online/tihkal/tihkal52.shtml Pyr-T - TiHKAL - Erowid]
• [https://isomerdesign.com/pihkal/read/tk/52 Pyr-T - TiHKAL - Isomer Design]

{{Serotonin receptor modulators}}

{{Tryptamines}}

Category:N,N-Dialkyltryptamines

Category:1-Pyrrolidinyl compounds

Category:Pyrrolidinylethylindoles

Category:Serotonin receptor modulators