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4C-T-2

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 477223594

| IUPAC_name = 1-[(2,5-dimethoxy-4-ethylthio)phenyl]butan-2-amine

| image = 4C-T-2 skeletal.svg

| tradename =

| pregnancy_category =

| legal_status = Uncontrolled

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 850007-13-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = AY9HDQ4A2H

| CAS_supplemental =
849919-79-5 (hydrochloride)

| ATC_prefix = none

| ATC_suffix =

| PubChem = 11197523

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 9372592

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 372719

| C=14 | H=23 | N=1 | O=2 | S=1

| smiles = COC1=C(CC(CC)N)C=C(OC)C(SCC)=C1

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = KLAWPCIXPDTGCZ-UHFFFAOYSA-N

}}

2,5-Dimethoxy-4-ethylthio-α-ethylphenethylamine (4C-T-2) is a synthetic drug of the phenethylamine, phenylisobutylamine, and 4C families. It is the α-ethylated analogue of 2C-T-2.

Pharmacology

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|+ {{Nowrap|4C-T-2 activities}}

TargetAffinity (Ki, nM)
5-HT1A5,339
5-HT1B>10,000
5-HT1D>10,000
5-HT1E9,879
5-HT1F{{Abbr|ND|No data}}
5-HT2A274 (Ki)
13.1–53 ({{Abbrlink|EC50|half-maximal effective concentration}})
78% ({{Abbrlink|Emax|maximal efficacy}})
5-HT2B58.1 (Ki)
630 ({{Abbr|EC50|half-maximal effective concentration}})
{{Abbr|ND|No data}} ({{Abbr|Emax|maximal efficacy}})
5-HT2C469 (Ki)
7.3–13.2 ({{Abbr|EC50|half-maximal effective concentration}})
86–121% ({{Abbr|Emax|maximal efficacy}})
5-HT3>10,000
5-HT4{{Abbr|ND|No data}}
5-HT5A1,587
5-HT6>10,000
5-HT73,829
α1A, α1B>10,000
α1D{{Abbr|ND|No data}}
α2A–α2C>10,000
β1>10,000
β2124.9
β3{{Abbr|ND|No data}}
D1, D2>10,000
D31,273
D4, D5>10,000
H1–H4>10,000
M1–M5>10,000
I1946.5
σ1514.6
σ2>10,000
{{Abbrlink|TAAR1|Trace amine-associated receptor 1}}{{Abbr|ND|No data}}
{{Abbrlink|SERT|Serotonin transporter}}>10,000 (Ki)
{{Abbrlink|NET|Norepinephrine transporter}}>10,000 (Ki)
{{Abbrlink|DAT|Dopamine transporter}}>10,000 (Ki)
{{Abbrlink|MAO-A|Monoamine oxidase A}}11,800 ({{Abbrlink|IC50|half-maximal inhibitory concentration}})
{{Abbrlink|MAO-B|Monoamine oxidase B}}>100,000 ({{Abbr|IC50|half-maximal inhibitory concentration}})
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| colspan="2" style="width: 1px; background-color:#eaecf0; text-align: center;" | Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: {{cite web | title=Kᵢ Database | website=PDSP | date=1 April 2025 | url=https://pdsp.unc.edu/kidb2/kidb/web/kis-results/index?KisResultsSearch%5Binput_receptors%5D=&KisResultsSearch%5Binput_sources%5D=&KisResultsSearch%5Binput_species%5D=&KisResultsSearch%5Binput_hot_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=14687&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D=&KisResultsSearch%5Binput_receptors%5D=&KisResultsSearch%5Binput_sources%5D=&KisResultsSearch%5Binput_species%5D=&KisResultsSearch%5Binput_hot_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=12951&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D= | access-date=1 April 2025}}{{cite web | last=Liu | first=Tiqing | title=BindingDB BDBM50164331 1-(4-Ethylsulfanyl-2,5-dimethoxy-benzyl)-propylamine::CHEMBL372719 | website=BindingDB | url=https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50164331 | access-date=1 April 2025}}{{cite journal | vauthors = Ray TS | title = Psychedelics and the human receptorome | journal = PLOS ONE | volume = 5 | issue = 2 | pages = e9019 | date = February 2010 | pmid = 20126400 | pmc = 2814854 | doi = 10.1371/journal.pone.0009019 | doi-access = free | bibcode = 2010PLoSO...5.9019R | url = }}{{cite journal | vauthors = Cunningham MJ, Bock HA, Serrano IC, Bechand B, Vidyadhara DJ, Bonniwell EM, Lankri D, Duggan P, Nazarova AL, Cao AB, Calkins MM, Khirsariya P, Hwu C, Katritch V, Chandra SS, McCorvy JD, Sames D | title = Pharmacological Mechanism of the Non-hallucinogenic 5-HT2A Agonist Ariadne and Analogs | journal = ACS Chem Neurosci | volume = 14 | issue = 1 | pages = 119–135 | date = January 2023 | pmid = 36521179 | pmc = 10147382 | doi = 10.1021/acschemneuro.2c00597 | url = }}{{cite journal | vauthors = Gallardo-Godoy A, Fierro A, McLean TH, Castillo M, Cassels BK, Reyes-Parada M, Nichols DE | title = Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling | journal = J Med Chem | volume = 48 | issue = 7 | pages = 2407–2419 | date = April 2005 | pmid = 15801832 | doi = 10.1021/jm0493109 | url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=61e1af109f88d1c41da1f218f9403dff12b5d98d| url-access = subscription }}

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

See also

References

{{Reflist}}

{{Psychedelics}}

{{Adrenergic receptor modulators}}

{{Serotonin receptor modulators}}

{{Phenethylamines}}

Category:5-HT2A agonists

Category:5-HT2C agonists

Category:4C (psychedelics)

Category:Phenylisobutylamines

Category:Thioethers