2C-T-36

2C-T-36
Clinical data
Other names2C-T-TFM; CYB210010; CYB-210010; CYB-2108; CYB2108; 2,5-Dimethoxy-4-(trifluoromethyl-sulfanyl)phenethylamine[1]
Drug classSerotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
Identifiers
  • 2-[2,5-dimethoxy-4-(trifluoromethylsulfanyl)phenyl]ethanamine
CAS Number
PubChem CID
Chemical and physical data
FormulaC11H14F3NO2S
Molar mass281.29 g·mol−1
3D model (JSmol)
  • COC1=CC(=C(C=C1CCN)OC)SC(F)(F)F
  • InChI=1S/C11H14F3NO2S/c1-16-8-6-10(18-11(12,13)14)9(17-2)5-7(8)3-4-15/h5-6H,3-4,15H2,1-2H3
  • Key:VOGDBAZLGHXJBS-UHFFFAOYSA-N

2C-T-36, also known as 2C-T-TFM, 2,5-dimethoxy-4-(trifluoromethylsulfanyl)phenethylamine, or CYB210010, is a psychedelic drug of the phenethylamine and 2C families related to other psychedelics such as 2C-TFM, 2C-T, and 2C-T-21 (2C-T-FE).[2][3]

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. This compound was ultimately first synthesised by Geoffrey Varty and colleagues at Irish biopharmaceutical company Helus Pharma (formerly Cybin) in 2023.[3]

It 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.[4] 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.[2][3] The interactions of 2C-T-36 with numerous other receptors and targets have also been described.[2] It has only been studied preclinically as of 2024 and is not known to have been tested in humans.[2][3]

It is a controlled substance in Canada under phenethylamine blanket-ban language.[5] The drug is not an explicitly controlled substance in the United States.[6]

Related drugs include the deuterated phenethylamine HLP005 (CYB005) and the deuterated substituted tryptamines HLP003 (CYB003) and HLP004 (CYB004).[7][8]

See also

References

  1. ^ "2-[2,5-Dimethoxy-4-(trifluoromethylsulfanyl)phenyl]ethanamine". PubChem. Retrieved 10 November 2024.
  2. ^ a b c d 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.
  3. ^ 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.
  4. ^ 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 
  5. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  6. ^ 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
  7. ^ Cano GH, Dean J, Abreu SP, Rodríguez AH, Abbasi C, Hinson M, et al. (December 2022). "Key Characteristics and Development of Psychoceuticals: A Review". Int J Mol Sci. 23 (24) 15777. doi:10.3390/ijms232415777. PMC 9779201. PMID 36555419.
  8. ^ Peplow M (June 2024). "Next-generation psychedelics: should new agents skip the trip?". Nat Biotechnol. 42 (6): 827–830. doi:10.1038/s41587-024-02285-1. PMID 38831049.
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