2C-T-21

Last updated

2C-T-21
2C-T-21 2DACS.svg
2C-T-21-3d-sticks.png
Clinical data
Other names4-(2-Fluoroethylthio)-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-(2-fluoroethylthio)phenethylamine; 2C-T-FE
Routes of
administration 		Oral [1]
Drug class Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • In general unscheduled
Pharmacokinetic data
Onset of action 15 min–1 hour [1]
Duration of action 7–10 hours [1]
Identifiers
  • 2-{{#parsoidfragment:2}}{4-[(2-fluoroethyl)sulfanyl]-2,5-dimethoxyphenyl}ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C12H18FNO2S
Molar mass 259.34 g·mol−1
3D model (JSmol)
  • COc1cc(SCCF)c(cc1CCN)OC
  • InChI=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 Yes check.svgY
  • Key:ZBUUUKBTOCTOPW-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

2C-T-21, also known as 4-(2-fluoroethylthio)-2,5-dimethoxyphenethylamine, is a psychedelic phenethylamine of the 2C family. [1] It is taken orally. [1]

Contents

2C-T-21 was first described in the scientific literature by Alexander Shulgin and colleagues in 1991. [2] Shortly after this, Shulgin described 2C-T-17 in greater detail in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). [1]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known And Loved), Alexander Shulgin lists the dose range as 8 to 12 mg orally and its duration as 7 to 10 hours. [1] Its onset is described as 15 minutes to 1 hour and peak effects occur after 1 to 2 hours. [1] The effects of 2C-T-21 have been described. [1]

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 (42 °C), [3] 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 ]

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 = 27 nM). [4] It produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents. [4]

Chemistry

Synthesis

The chemical synthesis of 2C-T-21 has been described. [1]

Analogues

Analogues of 2C-T-21 include 2C-T-2, 2C-T-21.5, and 2C-T-22, among others. [4] [1] [5]

History

2C-T-21 was first described in the scientific literature by Alexander Shulgin and colleagues in a journal article in 1991. [2] Shortly thereafter, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). [1] The potential applications of 2C-T-21 in psychedelic-assisted psychotherapy were explored by Myron Stolaroff. [6]

Society and culture

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. [7]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628. https://erowid.org/library/books_online/pihkal/pihkal049.shtml
  2. 1 2 Shulgin, Alexander T.; Shulgin, Ann; Jacob, Peyton (January 1991). "Letters to the Editor [Re: Stolaroff (1990) - Central Nervous System (CNS) Activity of Two New Psychoactive Compounds]". Journal of Psychoactive Drugs. 23 (1): 95–97 (95–96). doi:10.1080/02791072.1991.10472583. eISSN   2159-9777. ISSN   0279-1072. PMID   1941371. Archived from the original on July 13, 2025.
  3. ↑ "News from DEA, News Releases, 07/22/04". Archived from the original on February 8, 2008.
  4. 1 2 3 Halberstadt AL, Luethi D, Hoener MC, Trachsel D, Brandt SD, Liechti ME (January 2023). "Use of the head-twitch response to investigate the structure-activity relationships of 4-thio-substituted 2,5-dimethoxyphenylalkylamines" (PDF). Psychopharmacology (Berl). 240 (1): 115–126. doi:10.1007/s00213-022-06279-2. PMC   9816194 . PMID   36477925.
  5. ↑ Trachsel, D.; Lehmann, D.; Enzensperger, C. (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN   978-3-03788-700-4. OCLC   858805226. Archived from the original on August 21, 2025.
  6. ↑ Myron J. Stolaroff (1994). "Thanatos To Eros, 35 Years of Psychedelic Exploration". Multidisciplinary Association for Psychedelic Studies (MAPS).
  7. ↑ Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)
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