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2C-T

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2C-T
Clinical data
Other names2C-T-1; 4-Methylthio-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-methylthiophenethylamine
Routes of
administration		Oral[1]
Drug classSerotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • In general unscheduled
Pharmacokinetic data
Onset of action15 minutes[1]
Duration of action3–5 hours[1]
Identifiers
  • 2-[2,5-dimethoxy-4-(methylsulfanyl)phenyl]ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.215.648 Edit this at Wikidata
Chemical and physical data
FormulaC11H17NO2S
Molar mass227.32 g·mol−1
3D model (JSmol)
  • CSc1cc(OC)c(cc1OC)CCN
  • InChI=1S/C11H17NO2S/c1-13-9-7-11(15-3)10(14-2)6-8(9)4-5-12/h6-7H,4-5,12H2,1-3H3 checkY
  • Key:UPZMYCMLLQTYEM-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

2C-T, or 2C-T-1, also known as 4-methylthio-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.[1][2] It is taken orally.[1] The drug has a relatively short duration and is of relatively low potency among the 2C psychedelics.[1]

The drug acts as an agonist of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A receptor.[3] It is the parent compound of the 2C-T series of psychedelic phenethylamines, with derivatives such as 2C-T-2, 2C-T-4, 2C-T-7, and 2C-T-21, among many others.[1][2]

2C-T was first described in the scientific literature by David E. Nichols and Alexander Shulgin in 1976.[4][2] It was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1][2]

Use and effects

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In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 2C-T's dose range as 60 to 100 mg orally and its duration as 3 to 5 hours.[1] Its onset is described as 15 minutes and its effects are said to develop "very quickly but very quietly".[1] It is one of the shortest-acting of the 2C psychedelics as well as among the least potent.[1]

The effects of 2C-T have been reported to include being "really psychedelic", little or nothing in the way of psychedelic visuals, some fantasy with music, increased appreciation of poetry, things feeling "opened up" like with MDMA, being a possible MDMA substitute in this regard, feeling somewhat "generic" as a psychedelic, intellectual thinking overpowering emotions, conversational facilitation, tactile enhancement, enhanced eroticism, and stomach discomfort.[1]

Interactions

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

Pharmacology

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Pharmacodynamics

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2C-T shows affinity for the serotonin 5-HT2 receptors and is known to act as an agonist of the serotonin 5-HT2A and 5-HT2B receptors.[3][5] The drug shows no affinity for the monoamine transporters.[3]

Chemistry

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2C-T is in a class of compounds commonly known as phenethylamines, and is the 4-methylthio analogue of 2C-O, a positional isomer of mescaline. It is also the 2C analog of Aleph. The systematic name of the chemical is 2-(2,5-dimethoxy-4-(methylthio)phenyl)ethanamine. The CAS number of 2C-T is 61638-09-3.

Synthesis

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

Derivatives

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A large number of derivatives of 2C-T have been developed and described.[1] These include 2C-T-2, 2C-T-3, 2C-T-4, 2C-T-7, 2C-T-21, and CYB-210010 (2C-T-TFM or 2C-T-36), among many others.[1]

History

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2C-T was first synthesized and studied through a collaboration between David E. Nichols and Alexander Shulgin.[4] It was first described in the scientific literature in 1976.[4]

Society and culture

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Canada

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As of October 31, 2016; 2C-T is a controlled substance (Schedule III) in Canada.[6]

United States

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2C-T is unscheduled and unregulated in the United States; however its close similarity in structure and effects to 2C-T-7 could potentially subject possession and sale of 2C-T to prosecution under the Federal Analog Act. This seems to be the tack the federal government is taking in the wake of the DEA's Operation Web Tryp. A series of court cases in the US involving the prosecution of several online vendors were commenced in 2004 and resulted in a number of convictions.[7]

See also

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References

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  1. ^ a b c d e f g h i j k l m n o Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. 2C-T Entry in PiHKAL
  2. ^ a b c d e Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
  3. ^ a b c Luethi D, Trachsel D, Hoener MC, Liechti ME (May 2018). "Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs)". Neuropharmacology. 134 (Pt A): 141–148. doi:10.1016/j.neuropharm.2017.07.012. PMID 28720478.
  4. ^ a b c Nichols DE, Shulgin AT (October 1976). "Sulfur analogs of psychotomimetic amines". Journal of Pharmaceutical Sciences. 65 (10): 1554–1556. Bibcode:1976JPhmS..65.1554S. doi:10.1002/jps.2600651040. PMID 978423.
  5. ^ Pottie E, Poulie CB, Simon IA, Harpsøe K, D'Andrea L, Komarov IV, et al. (August 2023). "Structure-Activity Assessment and In-Depth Analysis of Biased Agonism in a Set of Phenylalkylamine 5-HT2A Receptor Agonists". ACS Chem Neurosci. 14 (15): 2727–2742. doi:10.1021/acschemneuro.3c00267. PMID 37474114.
  6. ^ "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". Canada Gazette. 4 May 2016.
  7. ^ "DEA Announces Arrests and Investigation". Erowid Psychoactive Vaults : Research Chemicals. July 22, 2004.
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