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2C-T-36, also known as 2,5-dimethoxy-4-(trifluoromethylsulfanyl)phenethylamine or 2C-T-TFM as well as CYB210010 or CYB2108, is a psychedelic drug of the phenethylamine and 2C families.[1][2]

Use and effects

The properties and effects of 2C-T-36 in humans appear to be unknown.[3][4][1][2]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

2C-T-36 has a Ki of 0.35 nM at the serotonin 5-HT2A receptor, and an EC50Tooltip half-maximal effective concentration of 4.1 nM at the serotonin 5-HT2A receptor and 7.3 nM at the serotonin 5-HT2C receptor, compared to 88 nM at the serotonin 5-HT2B receptor.[5] It is a potent, selective, long acting, and orally active agonist for the serotonin 5-HT2A and 5-HT2C receptors and produces psychedelic-like responding in several different animal species.[1][2] The interactions of 2C-T-36 with numerous other receptors and targets have also been described.[1]

Chemistry

Synthesis

The chemical synthesis of 2C-T-36 has been described.[3][1]

Analogues

Structure of CYB2108D, a deuterated analogue of 2C-T-36 (CYB2108).[6][7]

Analogues of 2C-T-36 (2C-T-TFM) include 2C-T-21 (2C-T-FE), 2C-T-21.5 (2C-T-DFE), 2C-T-22 (2C-T-TFE), 2C-T-28 (2C-T-FP), 2C-T-35 (2C-T-DFM), 2C-T, 2C-TFM, and 2C-TFE, among others.[3][4][1] Some other analogues include 2C-Se-TFM, trifluoromescaline (TFM), 3C-TFE (3C-trifluoroescaline), and tiflorex (flutiorex).[4][1] A deuterated isotopologue, CYB2108D (2C-T-36 with fully deuterated methoxy groups at 2 and 5 positions), is known.[6][7]

History

Alexander Shulgin attempted to synthesise this compound in the 1990s, and mentions it in his book PiHKAL (Phenethylamines I Have Known and Loved) under the entry for 2C-T-21, but was unsuccessful in producing a key intermediate and never assigned it a 2C-T number.[3] 2C-T-36 was ultimately first synthesised and named by Geoffrey Varty and colleagues at Irish biopharmaceutical company Helus Pharma (formerly Cybin) in 2023.[2]

Society and culture

Canada

2C-T-36 is a controlled substance in Canada under phenethylamine blanket-ban language.[8]

United States

The drug is not an explicitly controlled substance in the United States.[9]

Research

Other related drugs under development by Helus Pharma (formerly Cybin) include the deuterated phenethylamine HLP005 (CYB005) and the deuterated tryptamines HLP003 (CYB003) and HLP004 (CYB004).[10][11]

See also

References

  1. ^ a b c d e f g Varty GB, Canal CE, Mueller TA, Hartsel JA, Tyagi R, Avery K, et al. (April 2024). “Synthesis and Structure-Activity Relationships of 2,5-Dimethoxy-4-Substituted Phenethylamines and the Discovery of CYB210010: A Potent, Orally Bioavailable and Long-Acting Serotonin 5-HT2 Receptor Agonist”. Journal of Medicinal Chemistry. 67 (8): 6144–6188. doi:10.1021/acs.jmedchem.3c01961. PMID 38593423.
  2. ^ a b c d Palfreyman M, Varty G, Canal C, Hartsel J, Tyagi R, Avery K, et al. (December 2023). “ACNP 62nd Annual Meeting: Poster Abstracts P251 – P500: P405. Discovery and Preclinical Characterization of the Phenylalkylamine, CYB210010, a Potent and Long-Acting Serotonin 5-HT2A Receptor Agonist”. Neuropsychopharmacology. 48 (Suppl 1): 211–354 (299–299. doi:10.1038/s41386-023-01756-4. PMC 10729596. PMID 38040810.
  3. ^ a b c d Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. “A couple of additional efforts warrant comment. The reaction between trifluoromethyliodide and 2,5-dimethoxythiophenol should have produced 2,5-dimethoxyphenyl trifluoromethyl sulfide, but it didn’t produce anything.”
  4. ^ a b c 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 21 August 2025.
  5. ^ WO 2023156450, Nivorozhkin A, JA Hartsel, Canal CE, Salituro FG, Mueller TA, Greene BJ, Belser A, Avery KL, Reichelt AC, Varty GB, Palfreyman M, ”Therapeutic phenethylamine compositions and methods of use”, published 24 August 2023, assigned to Cybin Irl Limited 
  6. ^ a b “Therapeutic phenethylamine compositions and methods of use”. Google Patents. 18 August 2021. Retrieved 10 November 2024.
  7. ^ a b “2-[2,5-Bis(trideuteriomethoxy)-4-(trifluoromethylsulfanyl)phenyl]ethanamine”. PubChem. Retrieved 2 April 2026.
  8. ^ “Controlled Drugs and Substances Act”. Department of Justice Canada. Retrieved 19 January 2026.
  9. ^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
  10. ^ Cano GH, Dean J, Abreu SP, Rodríguez AH, Abbasi C, Hinson M, et al. (December 2022). “Key Characteristics and Development of Psychoceuticals: A Review”. International Journal of Molecular Sciences. 23 (24) 15777. doi:10.3390/ijms232415777. PMC 9779201. PMID 36555419.
  11. ^ Peplow M (June 2024). “Next-generation psychedelics: should new agents skip the trip?”. Nature Biotechnology. 42 (6): 827–830. doi:10.1038/s41587-024-02285-1. PMID 38831049.