2C-T
{{Infobox drug
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| image = 2C-T-Chemdraw.png
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| image2 = 2C-T animation.gif
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| routes_of_administration = Oral
| class = Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
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| duration_of_action = 3–5 hours
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| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 61638-09-3
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| PubChem = 12315927
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10438674
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| UNII = E5X0VFF7S4
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| ChEMBL = 127252
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| synonyms = 2C-T-1; 2,5-Dimethoxy-4-methylthiophenethylamine; 4-Methylthio-2,5-dimethoxyphenethylamine
| 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
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2C-T, or 2C-T-1, also known as 4-methylthio-2,5-dimethoxyphenethylamine, is a psychedelic and hallucinogenic drug of the 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 3 to 5{{nbsp}}hours for 2C-T.{{CitePiHKAL}} [http://www.erowid.org/library/books_online/pihkal/pihkal039.shtml 2C-T Entry in PiHKAL] It produces psychedelic and MDMA-like effects.
Interactions
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
Pharmacology
2C-T shows affinity for the serotonin 5-HT2 receptors and is known to act as an agonist of the serotonin 5-HT2A and 5-HT2B receptors.{{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}} 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-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. 2C-T shows no affinity for the monoamine transporters.
Chemistry
2C-T is in a class of compounds commonly known as phenethylamines, and is the 4-methylthio analogue of 2C-O, a positional isomer of mescaline. It is also the 2C analog of Aleph. The systematic name of the chemical is 2-(2,5-dimethoxy-4-(methylthio)phenyl)ethanamine. The CAS number of 2C-T is 61638-09-3.
=Derivatives=
History
2C-T was first synthesized and studied through a collaboration between David E. Nichols and Alexander Shulgin.{{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}} It was first described in the scientific literature in 1976.
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.
=Legal status=
==Canada==
As of October 31, 2016; 2C-T 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|title=Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)|date=4 May 2016}}
==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.{{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 }}
See also
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:Psychedelic phenethylamines