2C-T-21

Psychedelic phenethylamine drug From Wikipedia, the free encyclopedia

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]

Other names4-(2-Fluoroethylthio)-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-(2-fluoroethylthio)phenethylamine; 2C-T-FE
ATC code
  • None
Quick facts Clinical data, Other names ...
2C-T-21
Clinical data
Other names4-(2-Fluoroethylthio)-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-(2-fluoroethylthio)phenethylamine; 2C-T-FE
Routes of
administration
Oral[1][2]
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • In general unscheduled
Pharmacokinetic data
Onset of action15 min–1 hour[1]
Duration of action7–10 hours[1]
Identifiers
  • 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
FormulaC12H18FNO2S
Molar mass259.34 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 checkY
  • Key:ZBUUUKBTOCTOPW-UHFFFAOYSA-N checkY
  (verify)
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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.[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 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 (EC50Tooltip half-maximal effective concentration = 9.7 nM; EmaxTooltip maximal efficacy = 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

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