View source for 2C-T

{{Infobox drug
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| verifiedrevid = 477216538
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| image = 2C-T-Chemdraw.png
| width = 180px
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| image2 = 2C-T animation.gif
| width2 = 200px
| caption2 = 

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| routes_of_administration = [[Oral administration|Oral]]
| class = [[Serotonin]] [[5-HT2 receptor|5-HT<sub>2</sub> receptor]] [[agonist]]; [[Serotonergic psychedelic]]; [[Hallucinogen]]
| ATC_prefix = None
| ATC_suffix = 

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| duration_of_action = 3–5 hours<ref name=PiHKAL/>
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<!-- Identifiers -->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 61638-09-3
| CAS_supplemental = 
| PubChem = 12315927
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10438674
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = E5X0VFF7S4
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| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 127252
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| synonyms = 2C-T-1; 2,5-Dimethoxy-4-methylthiophenethylamine; 4-Methylthio-2,5-dimethoxyphenethylamine

<!-- Chemical data -->
| IUPAC_name = 2-[2,5-dimethoxy-4-(methylsulfanyl)phenyl]ethan-1-amine
| C=11 | H=17 | N=1 | O=2 | S=1 
| SMILES = CSc1cc(OC)c(cc1OC)CCN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H17NO2S/c1-13-9-7-11(15-3)10(14-2)6-8(9)4-5-12/h6-7H,4-5,12H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UPZMYCMLLQTYEM-UHFFFAOYSA-N
}}

'''2C-T''', or '''2C-T-1''', also known as '''4-methylthio-2,5-dimethoxyphenethylamine''', is a [[psychedelic drug|psychedelic]] and [[hallucinogenic drug]] of the [[2C's|2C family]].  It is used by some as an [[entheogen]]. It has structural and pharmacodynamic properties similar to the drugs [[mescaline]] and [[2C-T-2]].

==Effects==
In ''[[TiHKAL]]'', [[Alexander Shulgin]] lists a dose range of 60 to 100{{nbsp}}mg and a [[duration of action|duration]] of 3 to 5{{nbsp}}hours for 2C-T.<ref name="PiHKAL">{{CitePiHKAL}} [http://www.erowid.org/library/books_online/pihkal/pihkal039.shtml 2C-T Entry in PiHKAL]</ref> It produces [[psychedelic drug|psychedelic]] and [[MDMA]]-like effects.<ref name="PiHKAL" />

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

==Pharmacology==
2C-T shows [[affinity (pharmacology)|affinity]] for the [[serotonin]] [[5-HT2 receptor|5-HT<sub>2</sub> receptor]]s and is known to act as an [[agonist]] of the serotonin [[5-HT2A receptor|5-HT<sub>2A</sub>]] and [[5-HT2B receptor|5-HT<sub>2B</sub> receptor]]s.<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> The mechanism that produces 2C-T's hallucinogenic and entheogenic effects has not been specifically established, however it is most likely to result from serotonin 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. 2C-T shows no affinity for the [[monoamine transporter]]s.<ref name="LuethiTrachselHoener2018" />

==Chemistry==
2C-T is in a class of compounds commonly known as [[phenethylamine]]s, and is the 4-[[methyl]][[Thio-|thio]] [[analog (chemistry)|analogue]] of [[2C-O]], a [[positional isomer]] of mescaline.  It is also the [[2C's|2C]] analog of [[Aleph (psychedelic)|Aleph]].  The systematic name of the chemical is 2-(2,5-di[[methoxy]]-4-([[methyl]][[Thio-|thio]])[[phenyl]])ethanamine. The [[CAS number]] of 2C-T is 61638-09-3.

===Derivatives===
A large number of [[chemical derivative|derivative]]s of 2C-T have been developed and described. These include [[2C-T-2]], [[2C-T-3]], [[2C-T-4]], [[2C-T-7]], and [[2C-T-16]], among others.

==History==
2C-T was first [[chemical synthesis|synthesized]] and studied through a collaboration between [[David E. Nichols]] and [[Alexander Shulgin]].<ref name="NicholsShulgin1976">{{cite journal | vauthors = Nichols DE, Shulgin AT | title = Sulfur Analogs of Psychotomimetic Amines | journal = J Pharm Sci | volume = 65 | issue = 10 | pages = 1554–1556 | date = October 1976 | pmid = 978423 | doi = 10.1002/jps.2600651040 | url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=ccfa49101fe0e3039bd68c03263d22ae033cd3a7| url-access = subscription }}</ref> It was first described in the [[scientific literature]] in 1976.<ref name="NicholsShulgin1976" />

==Society and culture==
===Popularity===
2C-T is almost unknown on the black market although it has rarely been sold by "research chemical" companies.  Limited accounts of 2C-T can be found in the book ''[[PiHKAL]]''.<ref name=PiHKAL/>

===Legal status===
====Canada====
As of October 31, 2016; 2C-T 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|title=Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)|date=4 May 2016}}</ref>

====United States====
2C-T is unscheduled and unregulated in the [[United States]]; however its close similarity in structure and effects to [[2C-T-7]] could potentially subject possession and sale of 2C-T to prosecution under the [[Federal Analog Act]]. This seems to be the tack the federal government is taking in the wake of the DEA's [[Operation Web Tryp]]. A series of court cases in the US involving the prosecution of several online vendors were commenced in 2004 and resulted in a number of convictions.<ref name="urlErowid Psychoactive Vaults : Research Chemicals : DEA Announces Arrests and Investigation, July 22, 2004">{{cite web |url=http://www.erowid.org/psychoactives/research_chems/research_chems_info1.shtml |title=Erowid Psychoactive Vaults : Research Chemicals : DEA Announces Arrests and Investigation, July 22, 2004 }}</ref>

==See also==
* [[CYB-210010]]
* [[Substituted methoxyphenethylamine]]

==References==
{{Reflist}}

==External links==
* [https://isomerdesign.com/pihkal/explore/39 2C-T - Isomer Design]
* [https://www.bluelight.org/xf/threads/302863 The Big & Dandy 2C-T Thread - Bluelight]
* [https://www.erowid.org/library/books_online/pihkal/pihkal039.shtml 2C-T - PiHKAL - Erowid]
* [https://isomerdesign.com/pihkal/read/pk/39 2C-T - PiHKAL - Isomer Design]

{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Phenethylamines}}
{{Chemical classes of psychoactive drugs}}

[[Category:5-HT2A agonists]]
[[Category:5-HT2B agonists]]
[[Category:2C (psychedelics)]]
[[Category:Psychedelic phenethylamines]]
[[Category:Serotonin receptor agonists]]
[[Category:Thioethers]]