4C-T-2

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4C-T-2
Clinical data
Other names4-Ethylthio-2,5-dimethoxy-α-ethylphenethylamine
ATC code
  • None
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 1-[(2,5-dimethoxy-4-ethylthio)phenyl]butan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H23NO2S
Molar mass269.40 g·mol−1
3D model (JSmol)
  • COC1=C(CC(CC)N)C=C(OC)C(SCC)=C1
  • InChI=1S/C14H23NO2S/c1-5-11(15)7-10-8-13(17-4)14(18-6-2)9-12(10)16-3/h8-9,11H,5-7,15H2,1-4H3 checkY
  • Key:KLAWPCIXPDTGCZ-UHFFFAOYSA-N checkY
  (verify)

4C-T-2, also known as 2,5-dimethoxy-4-ethylthio-α-ethylphenethylamine, is a synthetic drug of the phenethylamine, phenylisobutylamine, and 4C families.[1][2][3] It is the α-ethylated analogue of 2C-T-2.[1][2][3]

Pharmacology

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4C-T-2 activities
Target Affinity (Ki, nM)
5-HT1A 5,339
5-HT1B >10,000
5-HT1D >10,000
5-HT1E 9,879
5-HT1F ND
5-HT2A 274 (Ki)
13.1–53 (EC50Tooltip half-maximal effective concentration)
78% (EmaxTooltip maximal efficacy)
5-HT2B 58.1 (Ki)
630 (EC50)
ND (Emax)
5-HT2C 469 (Ki)
7.3–13.2 (EC50)
86–121% (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A 1,587
5-HT6 >10,000
5-HT7 3,829
α1A, α1B >10,000
α1D ND
α2A–α2C >10,000
β1 >10,000
β2 124.9
β3 ND
D1, D2 >10,000
D3 1,273
D4, D5 >10,000
H1–H4 >10,000
M1–M5 >10,000
I1 946.5
σ1 514.6
σ2 >10,000
TAAR1Tooltip Trace amine-associated receptor 1 ND
SERTTooltip Serotonin transporter >10,000 (Ki)
NETTooltip Norepinephrine transporter >10,000 (Ki)
DATTooltip Dopamine transporter >10,000 (Ki)
MAO-ATooltip Monoamine oxidase A 11,800 (IC50Tooltip half-maximal inhibitory concentration)
MAO-BTooltip Monoamine oxidase B >100,000 (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [4][5][2][3][6]

4C-T-2 acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[2][3]

History

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4C-T-2 was first described in the scientific literature by at least 2005.[6] It was more fully characterized in 2010[2] and then in 2023.[3]

See also

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References

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  1. ^ a b 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. Retrieved 2 November 2024.
  2. ^ a b c d e Ray TS (February 2010). "Psychedelics and the human receptorome". Plos One. 5 (2): e9019. Bibcode:2010PLoSO...5.9019R. doi:10.1371/journal.pone.0009019. PMC 2814854. PMID 20126400.
  3. ^ a b c d e Cunningham MJ, Bock HA, Serrano IC, Bechand B, Vidyadhara DJ, Bonniwell EM, et al. (January 2023). "Pharmacological Mechanism of the Non-hallucinogenic 5-HT2A Agonist Ariadne and Analogs". ACS Chemical Neuroscience. 14 (1): 119–135. doi:10.1021/acschemneuro.2c00597. PMC 10147382. PMID 36521179. Table S2. 5-HT2A and 5-HT2B IP1 agonism assay summary (EC50 values, duplicate averages only), performed at Cerep, Eurofins France [...]
  4. ^ "Kᵢ Database". PDSP. 1 April 2025. Retrieved 1 April 2025.
  5. ^ Liu T. "BindingDB BDBM50164331 1-(4-Ethylsulfanyl-2,5-dimethoxy-benzyl)-propylamine::CHEMBL372719". BindingDB. Retrieved 1 April 2025.
  6. ^ a b Gallardo-Godoy A, Fierro A, McLean TH, Castillo M, Cassels BK, Reyes-Parada M, et al. (April 2005). "Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling". Journal of Medicinal Chemistry. 48 (7): 2407–2419. doi:10.1021/jm0493109. PMID 15801832.
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