Editing 2C-T-21

{{Short description|Psychedelic phenethylamine drug}}
{{Use mdy dates|date=June 2013}}
{{Infobox drug
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| verifiedrevid = 477216649
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| image = 2C-T-21 2DACS.svg
| width = 200px
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| image2 = 2C-T-21-3d-sticks.png
| width2 = 

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| routes_of_administration = [[Oral administration|Oral]]<ref name="pihkal" />
| class = [[Serotonergic psychedelic]]; [[Hallucinogen]]
| ATC_prefix = None
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<!-- Pharmacokinetic data -->
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| duration_of_action = 7–10 hours<ref name="pihkal" />
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<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|chemspider}}
| CAS_number = 207740-33-8
| CAS_supplemental = 
| PubChem = 44349972
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106231
| UNII = 720O3Q04GA
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| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 126582
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| synonyms = 4-(2-Fluoroethylthio)-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-(2-fluoroethylthio)phenethylamine

<!-- Chemical data -->
| IUPAC_name = 2-<nowiki/>{4-[(2-Fluoroethyl)sulfanyl]-2,5-dimethoxyphenyl}ethan-1-amine
| C=12 | H=18 | F=1 | N=1 | O=2 | S=1 
| SMILES = COc1cc(SCCF)c(cc1CCN)OC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H18FNO2S/c1-15-10-8-12(17-6-4-13)11(16-2)7-9(10)3-5-14/h7-8H,3-6,14H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZBUUUKBTOCTOPW-UHFFFAOYSA-N
}}

'''2C-T-21''', also known as '''4-(2-fluoroethylthio)-2,5-dimethoxyphenethylamine''', is a [[psychedelic drug|psychedelic]] [[phenethylamine]] of the [[2C (psychedelics)|2C family]] sometimes used as an [[entheogen]].  It was first synthesized by [[Alexander Shulgin]].

==Dosage==
In his book ''[[PiHKAL|PiHKAL (Phenethylamines i Have Known And Loved)]]'', Shulgin lists the dosage range as 8 to 12{{nbsp}}mg.<ref name="pihkal">{{Cite book | author = Alexander Shulgin | title = PiHKAL | url = http://www.erowid.org/library/books_online/pihkal/pihkal049.shtml | chapter = 2C-T-21 }}</ref>

==Effects==
2C-T-21 is generally taken orally and effects typically last 7 to 10{{nbsp}}hours.<ref name="pihkal" /> The potential psychotherapeutic applications of this chemical were explored by [[Myron Stolaroff]].{{citation needed|date=May 2019}}

==Pharmacology==
2C-T-21 shows high [[affinity (pharmacology)|affinity]] for the [[serotonin]] [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] (K<sub>i</sub> = 27{{nbsp}}nM).<ref name="HalberstadtLuethiHoener2023">{{cite journal | vauthors = Halberstadt AL, Luethi D, Hoener MC, Trachsel D, Brandt SD, Liechti ME | title = Use of the head-twitch response to investigate the structure-activity relationships of 4-thio-substituted 2,5-dimethoxyphenylalkylamines | journal = Psychopharmacology (Berl) | volume = 240 | issue = 1 | pages = 115–126 | date = January 2023 | pmid = 36477925 | pmc = 9816194 | doi = 10.1007/s00213-022-06279-2 | url = https://core.ac.uk/download/pdf/543784099.pdf}}</ref> It produces the [[head-twitch response]], a behavioral proxy of [[psychedelic drug|psychedelic]]-like effects, in rodents.<ref name="HalberstadtLuethiHoener2023" /> The mechanism that produces 2C-T-21's hallucinogenic and entheogenic effects has not been established; however, it may result from serotonin 5-HT<sub>2A</sub> receptor activation in the brain, a mechanism of action shared by all of the hallucinogenic tryptamines and phenethylamines for which the mechanism of action is known.

==Dangers==
On March 9, 2004, a 22-year-old [[quadriplegic]] man named James Edwards Downs in St. Francisville, Louisiana, consumed an unknown dose of 2C-T-21 by sticking his tongue into a vial of powder he had purchased online. He developed a temperature of {{convert|108|F|C}},<ref name="urlNews from DEA, News Releases, 07/22/04">{{cite web |url=http://www.dea.gov/pubs/pressrel/pr072204.html |title=News from DEA, News Releases, 07/22/04 |archive-url=https://web.archive.org/web/20080208165133/http://www.dea.gov/pubs/pressrel/pr072204.html |archive-date=February 8, 2008 |url-status=dead }}</ref> had a [[tonic-clonic seizure]], and slipped into a coma.  Four days later, on March 13, Downs died at Lane Memorial Hospital in Zachary, LA.{{Citation needed|date=December 2007}}

This death became part of a two-year DEA investigation called [[Operation Web Tryp]] which was launched in 2002. On July 22, 2004, the owners of American Chemical Supply were arrested on federal charges relating to distribution of [[Federal Analog Act|controlled substance analogues]] and the death of James Edwards Downs. Little is known about the toxicity of 2C-T-21 beyond this incident.

==Legal status==
2C-T-21 is unscheduled and uncontrolled in the United States, but possession and sales of 2C-T-21 would probably be prosecuted under the [[Federal Analog Act]] because of its structural similarities to [[2C-T-7]] and its known potential to cause death. In the wake of [[Operation Web Tryp]] in July 2004, at least one distributor faced charges as a consequence of the death of James Downs from 2C-T-21 overdose.

===Canada===
As of October 31, 2016, 2C-T-21 is a controlled substance (Schedule III) in Canada.<ref>[http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)]</ref>

==References==
{{Reflist}}

==External links==
* [https://isomerdesign.com/pihkal/explore/49 2C-T-21 - Isomer Design]
* [https://psychonautwiki.org/wiki/2C-T-21 2C-T-21 - PsychonautWiki]
* [http://www.erowid.org/chemicals/2ct21/ 2C-T-21 - Erowid]
* [https://www.bluelight.org/xf/threads/99432 The Big & Dandy 2C-T-21 Thread - Bluelight]
* [https://erowid.org/library/books_online/pihkal/pihkal049.shtml 2C-T-21 - PiHKAL - Erowid]
* [https://isomerdesign.com/pihkal/read/pk/49 2C-T-21 - PiHKAL - Isomer Design]

{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Phenethylamines}}

{{DEFAULTSORT:2c-T-21}}

[[Category:5-HT2A agonists]]
[[Category:2C (psychedelics)]]
[[Category:Designer drugs]]
[[Category:Fluoroethyl compounds]]
[[Category:Thioethers]]