2C-T-27

{{Infobox drug

| drug_name =

| image = 2C-T-27.svg

| width =

| caption =

| pronounce =

| tradename =

| Drugs.com =

| MedlinePlus =

| licence_CA =

| licence_EU =

| DailyMedID =

| licence_US =

| pregnancy_AU =

| pregnancy_category =

| dependency_liability =

| addiction_liability =

| routes_of_administration =

| class = Serotonin receptor agonist; Serotonin 5-HT_2A receptor agonist; Serotonergic psychedelic; Hallucinogen

| ATC_prefix =

| ATC_suffix =

| legal_status =

| bioavailability =

| protein_bound =

| metabolism =

| metabolites =

| onset =

| elimination_half-life =

| duration_of_action =

| excretion =

| CAS_number =

| CAS_supplemental =

| PubChem = 12063261

| PubChemSubstance =

| IUPHAR_ligand =

| DrugBank =

| ChemSpiderID =

| UNII =

| KEGG =

| ChEBI =

| ChEMBL =

| NIAID_ChemDB =

| PDB_ligand =

| synonyms = 4-Benzylthio-2,5-dimethoxyphenethylamine

| IUPAC_name = 2-(4-benzylsulfanyl-2,5-dimethoxyphenyl)ethanamine

| C=17 | H=21 | N=1 | O=2 | S=1

| SMILES = COC1=CC(=C(C=C1CCN)OC)SCC2=CC=CC=C2

| StdInChI = 1S/C17H21NO2S/c1-19-15-11-17(16(20-2)10-14(15)8-9-18)21-12-13-6-4-3-5-7-13/h3-7,10-11H,8-9,12,18H2,1-2H3

| StdInChIKey = GRZVJRPTNCONNT-UHFFFAOYSA-N

}}

2C-T-27, also known as 4-benzylthio-2,5-dimethoxyphenethylamine, is a serotonin 5-HT_2A receptor agonist and serotonergic psychedelic of the phenethylamine and 2C families.{{cite book | vauthors = Trachsel D, Lehmann D, Enzensperger C | title=Phenethylamine: von der Struktur zur Funktion | trans-title = Phenethylamines: From Structure to Function | publisher=Nachtschatten-Verlag | location=Solothurn | series=Nachtschatten-Science | year=2013 | isbn=978-3-03788-700-4 | oclc=858805226 | url=https://books.google.com/books?id=-Us1kgEACAAJ | language=de | access-date=29 January 2025 | pages=789–795 }}{{cite journal | vauthors = Trachsel D | title=Synthese von neuen (Phenylalkyl)aminen zur Untersuchung von Struktur–Aktivitätsbeziehungen. Mitteilung 2: 4-Thio-substituierte [2-(2,5-Dimethoxyphenyl)ethyl]amine (=2,5-Dimethoxybenzolethanamine) | trans-title=Synthesis of Novel (Phenylalkyl)amines for the Investigation of Structure–Activity Relationships. Part 2). 4-Thio-Substituted [2-(2,5-Dimethoxyphenyl)ethyl]amines (=2,5-Dimethoxybenzeneethanamines) | journal=Helvetica Chimica Acta | volume=86 | issue=7 | date=2003 | issn=0018-019X | doi=10.1002/hlca.200390210 | pages=2610–2619}}{{cite web | vauthors = Meyers-Riggs B | title=Shulgin's Sulfur Symphony | website=countyourculture | date=3 April 2011 | url=https://isomerdesign.com/countyourculture/2011/04/03/shulgins-sulfur-symphony-part-ii/ | access-date=17 February 2025 | quote=2C-T-27 (2,5-dimethoxy-4-benzylthiophenethylamine ) Synthesized by Daniel Trachsel but has not been bioassayed to public knowledge. [...] Trachsel, D. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helv. Chim. Acta, 5 Aug 2003, 86 (7), 2610–2619.}}{{cite journal | vauthors = Luethi D, Trachsel D, Hoener MC, Liechti ME | title = Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs) | journal = Neuropharmacology | volume = 134 | issue = Pt A | pages = 141–148 | date = May 2018 | pmid = 28720478 | doi = 10.1016/j.neuropharm.2017.07.012 | url = https://bitnest.netfirms.com/external/10.1016/j.neuropharm.2017.07.012 }} It was first synthesized and described by Daniel Trachsel in 2003.

In addition to the serotonin 5-HT_2A receptor, 2C-T-27 interacts with the serotonin 5-HT_2C receptor. It showed higher affinity for the serotonin 5-HT_2A receptor than any other 2C drug (K_i = 1.6{{nbsp}}nM), but its activational potency and efficacy were among the lowest ({{Abbrlink|EC₅₀|half-maximal effective concentration}} = 26{{nbsp}}nM; {{Abbrlink|E_max|maximal efficacy}} = 27%).{{cite journal | vauthors = Halberstadt AL, Luethi D, Hoener MC, Trachsel D, Brandt SD, Liechti ME | title = Use of the head-twitch response to investigate the structure-activity relationships of 4-thio-substituted 2,5-dimethoxyphenylalkylamines | journal = Psychopharmacology (Berl) | volume = 240 | issue = 1 | pages = 115–126 | date = January 2023 | pmid = 36477925 | pmc = 9816194 | doi = 10.1007/s00213-022-06279-2 | url = https://core.ac.uk/download/pdf/543784099.pdf}}

The drug produces the head-twitch response (HTR), a behavioral proxy of psychedelic effects, in rodents. However, the HTR induced by 2C-T-27 is relatively weak.

2C-T-27 has been reported to produce hallucinogenic effects in humans. Its dosage was reported by Trachsel to be 80{{nbsp}}mg or more orally and no duration was listed.