| Width | 250px |
|---|---|
| Routes of administration | Oral[1][2] |
| Class | Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen |
| Atc prefix | None |
| Duration of action | 12–18 hours[1][2] |
| Cas number | 207740-28-1 |
| Pubchem | 44349799 |
| Chemspiderid | 23206245 |
| Synonyms | 4-tert-Butylthio-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-tert-butylthiophenethylamine |
| C | 14 |
| H | 23 |
| N | 1 |
| O | 2 |
| S | 1 |
| Smiles | NCCc1cc(OC)c(cc1OC)SC(C)(C)C |
| Stdinchi | 1S/C14H23NO2S/c1-14(2,3)18-13-9-11(16-4)10(6-7-15)8-12(13)17-5/h8-9H,6-7,15H2,1-5H3 |
| Stdinchikey | PSVDMTZXLJTPNX-UHFFFAOYSA-N |
2C-T-9, also known as 4-tert-butylthio-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.[1][2][3] It is taken orally.[1][2]
Use and effects
According to Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved), the dose range of 2C-T-9 is 60 to 100 mg orally and its duration is 12 to 18 hours.[1][2][4] Its effects included impairment such that one would not feel comfortable to drive, more effects "to the body than to the head", "body energy", sleeping difficulties, and hangover.[1] The drug did not produce psychedelic visuals.[1] One of the reports of 2C-T-9 was rated as a "plus-three" on the Shulgin Rating Scale.[1]
Interactions
Pharmacology
Pharmacodynamics
2C-T-9 has been found to act as a serotonin 5-HT2A receptor agonist with modest potency (EC50 = 150 nM).[5] The drug failed to produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents at the assessed dose of 3 mg/kg, which was said to parallel its known low potency in humans.[5]
Chemistry
Synthesis
The chemical synthesis of 2C-T-9 has been described.[1]
History
2C-T-9 was first described in the scientific literature by Alexander Shulgin and colleagues in 1991.[3][1] This included in a journal article[3] and in his book PiHKAL (Phenethylamines I Have Known and Loved).[1]
Society and culture
Legal status
Canada
2C-T-9 is a controlled substance in Canada under phenethylamine blanket-ban language.[6]
See also
References
- ^
- ^ Shulgin AT (2003). "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived 13 July 2025 at the Wayback Machine.
- ^ Shulgin AT, Shulgin A, Jacob P (January 1991). "Central nervous system (CNS) activity of two new psychoactive compounds". Journal of Psychoactive Drugs. 23 (1): 95–96. doi:10.1080/02791072.1991.10472583. PMID 1941371
- ^ Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". Hallucinogens: An Update. Vol. 146. National Institute on Drug Abuse Research Monograph Series. National Institute on Drug Abuse. pp. 74–91. PMID 8742795. Archived 13 July 2025 at the Wayback Machine.
- ^ Varty GB, Canal CE, Mueller TA, Hartsel JA, Tyagi R, Avery K, Morgan ME, Reichelt AC, Pathare P, Stang E, Palfreyman MG, Nivorozhkin A (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". J Med Chem. 67 (8): 6144–6188. doi:10.1021/acs.jmedchem.3c01961. PMID 38593423
The 4-tert-butyl group was considered as a spot for potential hydroxylation by cytochrome P450s to discover analogs with short-lasting effects. However, 2C-t-Bu was a potent agonist at the 5-HT2A receptor (Ki = 9.9 nM, EC50 = 4.2 nM) and elicited a robust HTR (Supporting Information, Table S1), providing in vivo evidence that the tert-butyl group is not rapidly metabolized to an inactive compound in mice, despite predictions.
- ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.