pyr-T

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{{Infobox drug

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| verifiedrevid = 464376573

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| image = pyr-T.png

| width = 225px

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| routes_of_administration = Oral, inhalation

| class = Serotonin receptor agonist; Possible serotonergic psychedelic; Possible hallucinogen

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 14008-96-9

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| PubChem = 26393

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| ChemSpiderID = 24588

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| UNII = VZ689W7HWX

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| synonyms = N,N-Tetramethylenetryptamine; N,N-Pyrrolidinyltryptamine; Pyrrolidinyltryptamine; Pyr-Tryptamine; 3-(2-Pyrrolidinoethyl)indole

| IUPAC_name = 3-[2-(pyrrolidin-1-yl)ethyl]-1H-indole

| C=14 | H=18 | N=2

| SMILES = c2c(c1ccccc1[nH]2)CCN3CCCC3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C14H18N2/c1-2-6-14-13(5-1)12(11-15-14)7-10-16-8-3-4-9-16/h1-2,5-6,11,15H,3-4,7-10H2

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = CVTZCBLFHNGYDQ-UHFFFAOYSA-N

| melting_point = 193

| melting_high = 194

| melting_notes = (hydrochloride salt)

| boiling_point = 170

| boiling_high = 180

| boiling_notes = (freebase at 0.05 mm/Hg)

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Pyr-T, also known as N,N-tetramethylenetryptamine or as 3-(2-pyrrolidinoethyl)indole, is a lesser-known, possible psychedelic drug of the tryptamine family.{{cite book | vauthors = Brimblecombe RW, Pinder RM | chapter = Indolealkylamines and Related Compounds | title = Hallucinogenic Agents | location = Bristol | pages = 98–144 | date = 1975 | publisher = Wright-Scientechnica | isbn = 978-0-85608-011-1 | oclc = 2176880 | ol = OL4850660M | url = https://bitnest.netfirms.com/external/Books/978-0-85608-011-1 | quote = The cyclic analogue of DET, 3-(2-pyrrolidinoethyl)indole (4.13), was as active as the parent compound in behavioural tests in rodents, cats, and primates (Brimblecombe, 1967; Hunt and Brimblecombe, 1967; Brad Icy and Johnston, 1970). The compound was effective at doses down to 0·5 mg./kg. (s.c.) in disrupting the ability of monkeys to perform learned responses, but it is active only at levels which approach its lethal dose and it is unlikely to be tested in man. [...] Compounds of interest which have not been tested in man include [...] 5-methoxy-3-(2-pyrrolidinoethyl)indole, which is the most potent tryptamine so far revealed by the open field test, though its high toxicity will preclude tests in man (Brimblecombe, 1967; Hunt and Brimblecombe, 1967). }} It is the cyclized derivative of diethyltryptamine (DET) in which the N,N-diethyl groups have been fused into a pyrrolidine ring.

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 }} Toxicity testing was later performed by Hunt and Brimblecombe by 1967, and although a lethal dosage was found in rats, a value is not given.{{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 }} It was described as being as potent as DET in rodents, cats, and primates, but that it also had a poor margin of activity relative to toxic and was unlikely to be tested in humans. In his 1997 book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin reports 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 }}

Pyr-T produces few to no effects in humans, but some behavioral changes were observed in animal tests. Very little data exists about the pharmacological properties, metabolism, and toxicity of pyr-T.