Editing 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 = 

<!-- Clinical data -->
| pronounce = 
| tradename = 
| Drugs.com = 
| MedlinePlus = 
| licence_CA = 
| licence_EU = 
| DailyMedID = 
| licence_US = 
| pregnancy_AU = 
| pregnancy_category = 
| dependency_liability = 
| addiction_liability = 
| routes_of_administration = [[Oral administration|Oral]]<ref name="CitePiHKAL" />
| class = [[Serotonin]]; [[5-HT2 receptor|5-HT<sub>2</sub> receptor]] [[agonist]]; [[Serotonergic psychedelic]]; [[Hallucinogen]]
| ATC_prefix = None
| ATC_suffix = 

<!-- Legal status -->
| legal_status = 

<!-- Pharmacokinetic data -->
| bioavailability = 
| protein_bound = 
| metabolism = 
| metabolites = 
| onset = 
| elimination_half-life = 
| duration_of_action = 12–18 hours<ref name="CitePiHKAL" />
| excretion = 

<!-- Identifiers -->
| 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

<!-- Chemical data -->
| IUPAC_name = 2-<nowiki/>{2,5-Dimethoxy-4-[(propan-2-yl)sulfanyl]phenyl}ethan-1-amine
| 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 drug|psychedelic]] [[phenethylamine]] of the [[2C (psychedelics)|2C family]].<ref name="CitePiHKAL" /><ref name="ShulginManningDaley2011">{{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}}</ref> It was first synthesized by [[Alexander Shulgin]] and is used as [[entheogen]]ic [[recreational drug]].<ref name="CitePiHKAL" />

==Effects==
2C-T-4 produces psychedelic and entheogenic effects that develop slowly and can last 12 to 18{{nbsp}}hours.<ref name="CitePiHKAL" />  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.<ref name="CitePiHKAL">{{CitePiHKAL}}</ref>  Shulgin devoted a chapter in the first part of his book ''[[PiHKAL]]'' to this compound, describing an intense [[Shulgin Rating Scale|"plus-four"]] psychedelic experience mediated by a twelve milligram dose.

==Interactions==
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

2C drugs are [[drug metabolism|metabolized]] by the [[monoamine oxidase]] (MAO) [[enzyme]]s [[MAO-A]] and [[MAO-B]].<ref name="DeanStellpflugBurnett2013">{{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 = }}</ref><ref name="TheobaldMaurer2007">{{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 = }}</ref> [[Monoamine oxidase inhibitor]]s (MAOIs) such as [[phenelzine]], [[tranylcypromine]], [[moclobemide]], and [[selegiline]] may potentiate the effects of 2C drugs.<ref name="DeanStellpflugBurnett2013" /><ref name="TheobaldMaurer2007" /><ref name="HalmanKongSarris2024">{{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}}</ref> This may result in [[overdose]] and serious [[toxicity]].<ref name="HalmanKongSarris2024" /><ref name="DeanStellpflugBurnett2013" />

==Pharmacology==
{| class="wikitable floatleft" style="font-size:small;"
|+ {{Nowrap|2C-T-4 activities}}
|-
! [[Biological target|Target]] !! [[Affinity (pharmacology)|Affinity]] (K<sub>i</sub>, nM)
|-
| [[5-HT1A receptor|5-HT<sub>1A</sub>]] || 470–916
|-
| [[5-HT1B receptor|5-HT<sub>1B</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT1D receptor|5-HT<sub>1D</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT1E receptor|5-HT<sub>1E</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT1F receptor|5-HT<sub>1F</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT2A receptor|5-HT<sub>2A</sub>]] || 27.9–54 (K<sub>i</sub>)<br />5.5–220 ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}})<br />56–87% ({{Abbrlink|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT2B receptor|5-HT<sub>2B</sub>]] || {{Abbr|ND|No data}} (K<sub>i</sub>)<br />63–160 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />68–75% ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT2C receptor|5-HT<sub>2C</sub>]] || 180–295 (K<sub>i</sub>)<br />{{Abbr|ND|No data}} ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />{{Abbr|ND|No data}} ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT3 receptor|5-HT<sub>3</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT4 receptor|5-HT<sub>4</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT5A receptor|5-HT<sub>5A</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT6 receptor|5-HT<sub>6</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT7 receptor|5-HT<sub>7</sub>]] || {{Abbr|ND|No data}}
|-
| [[Alpha-1A adrenergic receptor|α<sub>1A</sub>]] || 11,000
|-
| [[Alpha-1B adrenergic receptor|α<sub>1B</sub>]], [[Alpha-1D adrenergic receptor|α<sub>1D</sub>]] || {{Abbr|ND|No data}}
|-
| [[Alpha-2A adrenergic receptor|α<sub>2A</sub>]] || 130–217
|-
| [[Alpha-2B adrenergic receptor|α<sub>2B</sub>]], [[Alpha-2C adrenergic receptor|α<sub>2C</sub>]] || {{Abbr|ND|No data}}
|-
| [[Beta-1 adrenergic receptor|β<sub>1</sub>]]–[[Beta-3 adrenergic receptor|β<sub>3</sub>]] || {{Abbr|ND|No data}}
|-
| [[D1 receptor|D<sub>1</sub>]] || 20,000
|-
| [[D2 receptor|D<sub>2</sub>]] || 16,000
|-
| [[D3 receptor|D<sub>3</sub>]] || 19,000
|-
| [[D4 receptor|D<sub>4</sub>]], [[D5 receptor|D<sub>5</sub>]] || {{Abbr|ND|No data}}
|-
| [[H1 receptor|H<sub>1</sub>]] || >25,000
|-
| [[H2 receptor|H<sub>2</sub>]]–[[H4 receptor|H<sub>4</sub>]] || {{Abbr|ND|No data}}
|-
| [[Muscarinic acetylcholine M1 receptor|M<sub>1</sub>]]–[[Muscarinic acetylcholine M5 receptor|M<sub>5</sub>]] || {{Abbr|ND|No data}}
|-
| [[I1 receptor|I<sub>1</sub>]] || {{Abbr|ND|No data}}
|-
| [[Sigma-1 receptor|σ<sub>1</sub>]], [[Sigma-2 receptor|σ<sub>2</sub>]] || {{Abbr|ND|No data}}
|-
| {{Abbrlink|TAAR1|Trace amine-associated receptor 1}} || 2,337–4,500 (K<sub>i</sub>) (mouse)<br />19–53 (K<sub>i</sub>) (rat)<br />3,700 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (mouse)<br />83 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (rat)<br />>30,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (human)<br />51% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) (mouse)<br />67% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) (rat)
|-
| {{Abbrlink|SERT|Serotonin transporter}} || >30,000 (K<sub>i</sub>)<br />113,000 ({{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />{{Abbr|ND|No data}} ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
| {{Abbrlink|NET|Norepinephrine transporter}} || 17,000 (K<sub>i</sub>)<br />134,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />{{Abbr|ND|No data}} ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
| {{Abbrlink|DAT|Dopamine transporter}} || >30,000 (K<sub>i</sub>)<br />294,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />{{Abbr|ND|No data}} ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|- class="sortbottom"
| 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:''' <ref name="PDSPKiDatabase">{{cite web | title=Kᵢ Database | website=PDSP | date=9 May 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=12948&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=14677&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D= | access-date=9 May 2025}}</ref><ref name="RickliLuethiReinisch2015">{{cite journal | vauthors = Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME | title = Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs) | journal = Neuropharmacology | volume = 99 | issue = | pages = 546–553 | date = December 2015 | pmid = 26318099 | doi = 10.1016/j.neuropharm.2015.08.034 | url = https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf}}</ref><ref name="LuethiTrachselHoener2018">{{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}}</ref><ref name="SimmlerBuchyChaboz2016">{{cite journal | vauthors = Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME | title = In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1 | journal = J Pharmacol Exp Ther | volume = 357 | issue = 1 | pages = 134–144 | date = April 2016 | pmid = 26791601 | doi = 10.1124/jpet.115.229765 | url = https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA | archive-url = https://web.archive.org/web/20250509235235/https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA | url-status = dead | archive-date = 2025-05-09 }}</ref>
|}

2C-T-4 acts as a [[serotonin]] [[5-HT2 receptor|5-HT<sub>2</sub> receptor]] [[agonist]], including of the serotonin [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]].<ref name="LuethiTrachselHoener2018" /><ref name="RickliLuethiReinisch2015" /> 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-HT<sub>2A</sub> 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==
2C-T-4 is the [[2C (psychedelics)|2-carbon]] [[homologous series|homolog]] of [[Aleph-4]]. The full chemical name is 2-[4-([[isopropyl]][[Thio-|thio]])-2,5-di[[methoxy]][[phenyl]]]-[[ethyl group|ethan]][[amine]].  The drug has [[structure|structural]] and [[pharmacodynamic]] properties similar to [[2C-T-7]] and [[2C-T-19]].{{citation needed|date=March 2015}}

===Homologue===
[[Image:Psi-2C-T-4.png|thumb|200px|right|Ψ-2C-T-4, the homologue of 2C-T-4.]]

2C-T-4 has a [[structural homologue|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&nbsp;mg.

At this dosage its duration was very short and it produced few effects, however based on the research into the better characterized compound [[Psi-DOM|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&nbsp;mg;<ref name="CitePiHKAL"/> 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.<ref>{{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}}</ref>

====China====
As of October 2015 2C-T-4 is a controlled substance in China.<ref>{{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 }}</ref>

====Denmark====
2C-T-4 is added to the list of Schedule B controlled substances.<ref>{{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) }}</ref>

====Sweden====
[[Riksdag|''Sveriges riksdags'']] health ministry [[:sv:Statens folkhälsoinstitut|''Statens folkhälsoinstitut'']] classified 2C-T-4 as "health hazard" under the act [[:sv:Lagen om förbud mot vissa hälsofarliga varor|''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.<ref>{{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 }}</ref>

====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.<ref>{{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}}</ref>

==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}}

[[Category:5-HT2A agonists]]
[[Category:5-HT2B agonists]]
[[Category:2C (psychedelics)]]
[[Category:Designer drugs]]
[[Category:Isopropyl compounds]]
[[Category:TAAR1 agonists]]
[[Category:Thioethers]]