:2C-T-4
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477216693
| drug_name =
| image = 2C-T-4 2DACS.svg
| width = 200px
| caption =
| image2 = 2C-T-4-3d-sticks.png
| width2 = 200px
| caption2 =
| pronounce =
| tradename =
| Drugs.com =
| MedlinePlus =
| licence_CA =
| licence_EU =
| DailyMedID =
| licence_US =
| pregnancy_AU =
| pregnancy_category =
| dependency_liability =
| addiction_liability =
| routes_of_administration = Oral
| class = Serotonin; 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
| ATC_prefix = None
| ATC_suffix =
| legal_status =
| bioavailability =
| protein_bound =
| metabolism =
| metabolites =
| onset =
| elimination_half-life =
| duration_of_action = 12–18 hours
| excretion =
| CAS_number_Ref = {{cascite|correct|chemspider}}
| CAS_number = 207740-25-8
| CAS_supplemental =
| PubChem = 44350070
| PubChemSubstance =
| IUPHAR_ligand =
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106232
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 558WSD71D4
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C22735
| ChEBI =
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 338259
| NIAID_ChemDB =
| PDB_ligand =
| synonyms = 4-Isopropylthio-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-isopropylthiophenethylamine
| IUPAC_name = 2-
| C=13 | H=21 | N=1 | O=2 | S=1
| SMILES = CC(C)Sc1cc(OC)c(cc1OC)CCN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C13H21NO2S/c1-9(2)17-13-8-11(15-3)10(5-6-14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HDYZSVKZKDPLDT-UHFFFAOYSA-N
}}
2C-T-4, also known as 4-isopropylthio-2,5-dimethoxyphenethylamine, is a psychedelic phenethylamine of the 2C family.{{cite book | vauthors = Shulgin A, Manning T, Daley P | title=The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds | publisher=Transform Press | location=Berkeley | volume=1 | year=2011 | isbn=978-0-9630096-3-0 | url=https://books.google.com/books?id=68-huAAACAAJ}} It was first synthesized by Alexander Shulgin and is used as entheogenic recreational drug.
Effects
2C-T-4 produces psychedelic and entheogenic effects that develop slowly and can last 12 to 18{{nbsp}}hours. While users may experience virtually no effects for the first hour after ingestion, results vary drastically between individuals and range from hallucination and euphoria to intense sickness and anxiety.{{CitePiHKAL}} Shulgin devoted a chapter in the first part of his book PiHKAL to this compound, describing an intense "plus-four" psychedelic experience mediated by a twelve milligram dose.
Interactions
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
2C drugs are metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.{{cite journal | vauthors = Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM | title = 2C or not 2C: phenethylamine designer drug review | journal = J Med Toxicol | volume = 9 | issue = 2 | pages = 172–178 | date = June 2013 | pmid = 23494844 | pmc = 3657019 | doi = 10.1007/s13181-013-0295-x | url = }}{{cite journal | vauthors = Theobald DS, Maurer HH | title = Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series) | journal = Biochem Pharmacol | volume = 73 | issue = 2 | pages = 287–297 | date = January 2007 | pmid = 17067556 | doi = 10.1016/j.bcp.2006.09.022 | url = }} Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C drugs.{{Cite journal |vauthors=Halman A, Kong G, Sarris J, Perkins D |date=January 2024 |title=Drug-drug interactions involving classic psychedelics: A systematic review |journal=J Psychopharmacol |volume=38 |issue=1 |pages=3–18 |doi=10.1177/02698811231211219 |pmc=10851641 |pmid=37982394}} This may result in overdose and serious toxicity.
Pharmacology
2C-T-4 acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A receptor. The mechanism that produces 2C-T-4's hallucinogenic and entheogenic effects has not been specifically established, however it is most likely to result from 5-HT2A receptor activation in the brain, a mechanism of action shared by all of the hallucinogenic tryptamines and phenethylamines for which the mechanism of action is known.
Chemistry
=Homologue=
2C-T-4 has a homologue, the structural isomer Ψ-2C-T-4 (2,6-dimethoxy-4-(i)-propylthiophenethylamine). This compound was tested by Alexander Shulgin at a dose of 12 mg.
At this dosage its duration was very short and it produced few effects, however based on the research into the better characterized compound Ψ-DOM, the potency of Ψ-2C-T-4 is likely to be around 1/3 that of 2C-T-4 itself, so a more effective dosage of Ψ-2C-T-4 might be in the region of 20–60 mg; however high doses such as this might well be associated with toxic side effects, and so extreme caution would be advised.
Society and culture
=Popularity=
2C-T-4 is relatively unknown on the black market, but has been sold to a limited extent on the research chemical market.{{Citation needed|date=May 2025}}
=Legal status=
==Canada==
As of October 31, 2016, 2C-T-4 is a controlled substance (Schedule III) in Canada.{{Cite web|url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php| work = Canada Gazette | title = Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)|date=4 May 2016}}
==China==
As of October 2015 2C-T-4 is a controlled substance in China.{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | trans-title = Notice on the issuance of the "Regulations on the Listing of Non-Medicinal Narcotic Drugs and Psychotropic Drugs" | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}
==Denmark==
2C-T-4 is added to the list of Schedule B controlled substances.{{cite web |url=https://www.retsinformation.dk/Forms/R0710.aspx?id=137169 |title = Bekendtgørelse om euforiserende stoffer | trans-title = Executive Order on Euphoriant Drugs | language = Danish | work = Retsinformation (legal information) }}
==Sweden==
Sveriges riksdags health ministry Statens folkhälsoinstitut classified 2C-T-4 as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Jul 15, 2007, in their regulation SFS 2007:600 listed as 2,5-dimetoxi-4-isopropyltiofenetylamin (2C-T-4), making it illegal to sell or possess.{{cite web | vauthors = Larsson M | date = 14 June 2007 |url=http://www.notisum.se/rnp/sls/sfs/20070600.pdf | title = Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor | trans-title = Ordinance amending the Ordinance (1999:58) on the prohibition of certain goods hazardous to health | language = Swedish |work = Svensk författningssamling (Swedish Constitution) |access-date=January 24, 2022 |archive-date=September 29, 2013 |archive-url=https://web.archive.org/web/20130929062843/http://www.notisum.se/rnp/sls/sfs/20070600.pdf |url-status=dead }}
==United States==
As of July 9, 2012, 2C-T-4 is a Schedule I substance in the United States, under the Synthetic Drug Abuse Prevention Act of 2012.{{cite web| vauthors = Portman RJ |title=Synthetic Drug Abuse Prevention Act of 2012 |url= http://www.govtrack.us/congress/bills/112/s3190/text|publisher=Govtrack|access-date=22 July 2012}}
References
{{Reflist}}
External links
- [https://isomerdesign.com/pihkal/explore/41 2C-T-4 - Isomer Design]
- [https://www.erowid.org/chemicals/2ct4/2ct4.shtml 2C-T-4 - Erowid]
- [https://www.bluelight.org/xf/threads/288368 The Big & Dandy 2C-T-4 Thread - Bluelight]
- [http://www.erowid.org/library/books_online/pihkal/pihkal041.shtml 2C-T-4 - PiHKAL - Erowid]
- [http://pihkal.info/read.php?domain=pk&id=41 2C-T-4 - PiHKAL - Isomer Design]
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{TAAR modulators}}
{{Phenethylamines}}