Chemistry:2C-T-21

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

The drug acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A receptor.[3]

2C-T-21 was first described in the scientific literature by Alexander Shulgin and colleagues in 1991.[4] Shortly after this, Shulgin described 2C-T-21 in greater detail in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1] The drug has been encountered as a novel designer drug.[2]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known And Loved) and other publications, Alexander Shulgin lists 2C-T-21's dose as 8 to 12 mg orally and its duration as 7 to 10 hours.[1][5][6][4][2] However, a wider dose range of 10 to 20 mg orally has also been reported.[7][8] 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 reported to include little in the way of visuals, intense after-images, difficult to define mental changes, feeling stoned, time dilation, mood enhancement or pleasantness, no euphoria, talkativeness, enhanced communication, feelings of closeness with others, feelings of inner strength and peace, no insights, and push of energy.[1] Other effects included mental confusion, memory impairment, little or no body load, no nausea, no nystagmus, chills, yawning and ear popping, and no appetite loss.[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),[9] 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 and 5-HT2C receptors (Ki = 27.7 nM and 72.7 nM, respectively).[3] It has been found to act as a potent partial agonist of the serotonin 5-HT2A receptor (EC50 = 9.7 nM; Emax = 69%) and of the serotonin 5-HT2B receptor (EC50 = 102 nM; Emax = 32%).[3] The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[3]

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.[3][1][7]

History

2C-T-21 was first described in the scientific literature by Alexander Shulgin and colleagues in a journal article in 1991.[4] 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.[10] The drug was encountered as a novel designer drug online in 2014 and in the Netherlands in 2019.[2]

Society and culture

Canada

As of October 31, 2016, 2C-T-21 is a controlled substance (Schedule III) in Canada.[11]

United States

2C-T-21 is unscheduled and uncontrolled in the United States,[12] 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.

See also

References

  1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml.  https://www.erowid.org/library/books_online/pihkal/pihkal049.shtml
  2. ↑ 2.0 2.1 2.2 2.3 2.4 "2C-T-21" (in ru). https://aipsin.com/newsubstance/704/. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 "Use of the head-twitch response to investigate the structure-activity relationships of 4-thio-substituted 2,5-dimethoxyphenylalkylamines". Psychopharmacology 240 (1): 115–126. January 2023. doi:10.1007/s00213-022-06279-2. PMID 36477925. 
  4. ↑ 4.0 4.1 4.2 "Central nervous system (CNS) activity of two new psychoactive compounds". Journal of Psychoactive Drugs 23 (1): 95–96. January 1991. doi:10.1080/02791072.1991.10472583. PMID 1941371. https://bibliography.maps.org/resources/download/11956. 
  5. ↑ "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". Hallucinogens: An Update. National Institute on Drug Abuse Research Monograph Series. 146. National Institute on Drug Abuse. 1994. pp. 74–91. https://bibliography.maps.org/resources/download/11534. 
  6. ↑ "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://bibliography.maps.org/resources/download/12634. 
  7. ↑ 7.0 7.1 (in de) Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. 2013. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. 
  8. ↑ "Fluorine in psychedelic phenethylamines". Drug Test Anal 4 (7–8): 577–590. 2012. doi:10.1002/dta.413. PMID 22374819. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=c7b41be36b1f580a264a752521d151e6e2d9409d. "The psychedelic fluoro derivative 2,5-dimethoxy-4-(2- fluoroethylthio)phenethylamine (2C-T-21, 23) has been prepared and was initially investigated by Shulgin and Shulgin.[3] Psychoactive effects have been reported to last 7-10 h at dosage levels of 8–12 mg[3] and 10–20 mg,[54] respectively. It is structurally related to numerous other 2C-T derivatives and most closely related to the fluorine-free derivative 2,5-dimethoxy-4-ethylthiophenethylamine (2C-T-2, 24. 12–25 mg, 6–8 h), which is only slightly less potent although it was reported to vary in its psychological effects.[3]". 
  9. ↑ "News from DEA, News Releases, 07/22/04". http://www.dea.gov/pubs/pressrel/pr072204.html. 
  10. ↑ "Thanatos To Eros, 35 Years of Psychedelic Exploration". Multidisciplinary Association for Psychedelic Studies (MAPS). 1994. http://www.maps.org/index.php?option=com_content&view=article&id=5406. 
  11. ↑ Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)
  12. ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026, https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf 



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