2C-T-22

Last updated

2C-T-22
2CT22 structure.png
Clinical data
Other names4-(2,2,2-Trifluoroethylthio)-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-(2,2,2-trifluoroethylthio)phenethylamine
Routes of
administration 		Oral [1]
Drug class Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action ~6 hours [1]
Identifiers
  • 2-[2,5-dimethoxy-4-(2,2,2-trifluoroethylsulfanyl)phenyl]ethanamine
CAS Number
PubChem CID
Chemical and physical data
Formula C12H16F3NO2S
Molar mass 295.32 g·mol−1
3D model (JSmol)
  • COC1=CC(=C(C=C1CCN)OC)SCC(F)(F)F
  • InChI=1S/C12H16F3NO2S/c1-17-9-6-11(19-7-12(13,14)15)10(18-2)5-8(9)3-4-16/h5-6H,3-4,7,16H2,1-2H3
  • Key:LDOOFVKAIHFXAR-UHFFFAOYSA-N

2C-T-22, also known as 4-(2,2,2-trifluoroethylthio)-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine, 2C, and 2C-T-x families. [1] [2] It is closely related to 2C-T-21 (the 4-(2-fluoroethylthio) analogue and 2C-T-21.5 (the 4-(2,2-difluoroethylthio) analogue). [1] [2]

Contents

Use and effects

2C-T-22 was briefly described by Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in the 2C-T-21 entry, but Shulgin only partially completed the chemical synthesis of 2C-T-22 and did not test it. [2] Subsequently, Daniel Trachsel completed the synthesis of 2C-T-22 and defined its dose as greater than 10 mg orally and its duration as approximately 6 hours. [1] A total dose of 5 mg plus 5 mg plus 6 mg produced the first signs of effects, but higher doses were not explored. [1] [3] Hence, its precise dose range remains unknown. [4] [1] [3]

Interactions

Pharmacology

Pharmacodynamics

2C-T-22 shows affinity for the serotonin 5-HT2A receptor (Ki = 16–102 nM) and the serotonin 5-HT2C receptor (Ki = 28–151 nM). [1] [5] It has been found to be a potent partial agonist of the serotonin 5-HT2A and 5-HT2B receptors. [5] Other receptor and target interactions have also been described. [5]

History

2C-T-22 was first described in the scientific literature by Shulgin in his book PiHKAL in 1991. [2] Subsequently, Trachsel described and completed the synthesis of 2C-T-22 in 2003 [6] and he and his colleagues defined its properties in humans in 2013. [1] [3]

Society and culture

Canada

2C-T-22 is a controlled substance in Canada under phenethylamine blanket-ban language. [7]

See also

References

  1. 1 2 3 4 5 6 7 8 9 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. pp. 789–790, 791, 794. ISBN   978-3-03788-700-4. OCLC   858805226. Archived from the original on 21 August 2025.
  2. 1 2 3 4 Shulgin A, Shulgin A (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
  3. 1 2 3 Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID   22374819. In comparison with 2C-T-2 (24: 12–25 mg, 6–8 h), progressive terminal fluorination of the 4-EtS group either increased (2C-T-21, 23: 8–12 mg, 7–10 h, shown by Shulgin[3]) or maintained (2C-T-21.5, 37: 12–30 mg, 8–14 h) human potency according to the 'double conscious' technique (Figure 3, A).[68] The trifluoroethyl derivative 2C-T-22 (38) was not investigated sufficiently to draw any conclusions. At the [ 3 H]LSD labelled cloned h5-HT2A receptor, 2C-T-21.5 (37; Ki = 146 nM) and 2C-T-22 (38; Ki = 69nM) showed fairly high affinities but no further comparison can be made as the affinities of 24 and 23 are currently unknown. [...] Within the 2,4,5-series, some 14 novel fluorinated derivatives have been described (37, 38, 40, 42, 47–54, 56, 57).
  4. ↑ Luethi D, Liechti ME (October 2018). "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". The International Journal of Neuropsychopharmacology. 21 (10): 926–931. doi:10.1093/ijnp/pyy047. PMC   6165951 . PMID   29850881.
  5. 1 2 3 Luethi D, Trachsel D, Hoener MC, Liechti ME (May 2018). "Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs)". Neuropharmacology. 134 (Pt A): 141–148. doi:10.1016/j.neuropharm.2017.07.012. PMID   28720478.
  6. ↑ Trachsel D (2003). "Synthese von neuen (Phenylalkyl)aminen zur Untersuchung von Struktur–Aktivitätsbeziehungen. Mitteilung 2: 4‐Thio‐substituierte [2‐(2,5‐Dimethoxyphenyl)ethyl]amine (=2,5‐Dimethoxybenzolethanamine)" . Helvetica Chimica Acta. 86 (7): 2610–2619. doi:10.1002/hlca.200390210. ISSN   0018-019X . Retrieved 11 November 2025.
  7. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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