2C-T-9

Last updated
2C-T-9
2C-T-9 v2.svg
Clinical data
Other names4-tert-Butylthio-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-tert-butylthiophenethylamine
Routes of
administration 		Oral [1] [2]
Drug class Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action 12–18 hours [1] [2]
Identifiers
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
Formula C14H23NO2S
Molar mass 269.40 g·mol−1
3D model (JSmol)
  • NCCc1cc(OC)c(cc1OC)SC(C)(C)C
  • InChI=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
  • Key: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]

Contents

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 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 '+++' on the Shulgin Rating Scale. [1]

Interactions

Pharmacology

2C-T-9 has been found to act as a serotonin 5-HT2A receptor agonist with modest potency (EC50 Tooltip half-maximal effective concentration = 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]

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]

See also

References

  1. 1 2 3 4 5 6 7 8 9 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628.
  2. 1 2 3 4 Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN   978-0-12-433951-4.
  3. 1 2 3 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. eISSN   2159-9777. PMID   1941371.
  4. ↑ Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.). Hallucinogens: An Update (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91. PMID   8742795.
  5. 1 2 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.


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