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2C-T-21
Psychedelic phenethylamine drug
Psychedelic phenethylamine drug
| Field | Value | |||||
|---|---|---|---|---|---|---|
| Verifiedfields | changed | |||||
| Watchedfields | changed | |||||
| verifiedrevid | 477216649 | |||||
| image | 2C-T-21 2DACS.svg | |||||
| image_class | skin-invert-image | |||||
| width | 250px | |||||
| image2 | 2C-T-21-3d-sticks.png | |||||
| image_class2 | bg-transparent | |||||
| width2 | 225px | |||||
| routes_of_administration | Oral | |||||
| class | Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen | |||||
| ATC_prefix | None | |||||
| legal_status | In general unscheduled | |||||
| onset | 15 min–1 hour | |||||
| duration_of_action | 7–10 hours | |||||
| CAS_number_Ref | ||||||
| CAS_number | 207740-33-8 | |||||
| PubChem | 44349972 | |||||
| ChemSpiderID_Ref | ||||||
| ChemSpiderID | 21106231 | |||||
| UNII | 720O3Q04GA | |||||
| ChEMBL_Ref | ||||||
| ChEMBL | 126582 | |||||
| synonyms | 4-(2-Fluoroethylthio)-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-(2-fluoroethylthio)phenethylamine; 2C-T-FE | |||||
| IUPAC_name | 2-{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 | ||||||
| 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 | ||||||
| StdInChIKey | ZBUUUKBTOCTOPW-UHFFFAOYSA-N |
| Drugs.com =
| elimination_half-life =
2C-T-21, also known as 4-(2-fluoroethylthio)-2,5-dimethoxyphenethylamine, is a psychedelic phenethylamine of the 2C family. It is taken orally.
2C-T-21 was first described in the scientific literature by Alexander Shulgin and colleagues in 1991. Shortly after this, Shulgin described 2C-T-21 in greater detail in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). The drug has been encountered as a novel designer drug.
Use and effects
In his book PiHKAL (Phenethylamines I Have Known And Loved), Alexander Shulgin lists the dose range as 8 to 12mg orally and its duration as 7 to 10hours. Its onset is described as 15minutes to 1hour and peak effects occur after 1 to 2hours. The effects of 2C-T-21 have been described.
Toxicity
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 108 F, 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.
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 controlled substance analogues and the death of James Edwards Downs. Little is known about the toxicity of 2C-T-21 beyond this incident.
Interactions
Pharmacology
Pharmacodynamics
2C-T-21 shows high affinity for the serotonin 5-HT2A receptor (Ki = 27nM). It produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.
Chemistry
Synthesis
The chemical synthesis of 2C-T-21 has been described.
Analogues
Analogues of 2C-T-21 include 2C-T-2, 2C-T-21.5, and 2C-T-22, among others.
History
2C-T-21 was first described in the scientific literature by Alexander Shulgin and colleagues in a journal article in 1991. Shortly thereafter, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). The potential applications of 2C-T-21 in psychedelic-assisted psychotherapy were explored by Myron Stolaroff. The drug was encountered as a novel designer drug online in 2014 and in the Netherlands in 2019.
Society and culture
Legal status
Canada
As of October 31, 2016, 2C-T-21 is a controlled substance (Schedule III) in Canada.
United States
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.
References
References
- {{CitePiHKAL https://erowid.org/library/books_online/pihkal/pihkal049.shtml
- "2C-T-21".
- "News from DEA, News Releases, 07/22/04".
- (January 2023). "Use of the head-twitch response to investigate the structure-activity relationships of 4-thio-substituted 2,5-dimethoxyphenylalkylamines". Psychopharmacology.
- (2013). "Phenethylamine: von der Struktur zur Funktion". Nachtschatten-Verlag.
- (January 1991). "Central nervous system (CNS) activity of two new psychoactive compounds". Journal of Psychoactive Drugs.
- (1994). "Thanatos To Eros, 35 Years of Psychedelic Exploration". Multidisciplinary Association for Psychedelic Studies (MAPS).
- [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)]
- (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.
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