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2C-T-9

2C-T-9
Clinical data
Other names4-tert-Butylthio-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-tert-butylthiophenethylamine
Routes of
administration		Oral[1][2]
Drug classSerotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action12–18 hours[1][2]
Identifiers
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H23NO2S
Molar mass269.40 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]

Use and effects

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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

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

Pharmacology

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2C-T-9 has been found to act as a serotonin 5-HT2A receptor agonist with modest potency (EC50Tooltip 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

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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

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References

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  1. ^ a b c d e f g h i Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  2. ^ a b c d 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. ^ a b c 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. ^ a b 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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