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{{Short description|Psychedelic phenethylamine drug}}
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{{Use mdy dates|date=June 2013}}
{{chembox
{{chembox
| Verifiedfields = changed
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| verifiedrevid = 413115280
| Watchedfields = changed
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| ImageFile1 = Structure of 2C-T-21.png
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| verifiedrevid = 477216649
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| ImageFile1 = 2C-T-21 2DACS.svg
| ImageSize1 = 200px
| ImageSize1 = 200px
| ImageFile2 = 2C-T-21-3d-sticks.png
| ImageFile2 = 2C-T-21-3d-sticks.png
| ImageSize2 = 200px
| ImageSize2 = 200px
| PIN = 2-<nowiki/>{4-[(2-Fluoroethyl)sulfanyl]-2,5-dimethoxyphenyl}ethan-1-amine
| IUPACName = 2-[2,5-Dimethoxy-4-(2-fluoroethylthio)phenyl]ethanamine
| OtherNames =
| OtherNames = 4-(2-Fluoroethylthio)-2,5-dimethoxyphenethylamine
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZBUUUKBTOCTOPW-UHFFFAOYSA-N
| StdInChIKey = ZBUUUKBTOCTOPW-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|chemspider}}
| CASNo = 207740-33-8
| CASNo = 207740-33-8
| PubChem =
| PubChem = 44349972
| UNII = 720O3Q04GA
| SMILES = COc1cc(SCCF)c(cc1CCN)OC
| SMILES = COc1cc(SCCF)c(cc1CCN)OC
}}
}}
| Section2 = {{Chembox Properties
| Section2 = {{Chembox Properties
| C=12 | H=18 | F=1 | N=1 | O=2 | S=1
| Formula = C<sub>12</sub>H<sub>18</sub>FNO<sub>2</sub>S
| MolarMass = 259.34 g/mol
| Appearance =
| Appearance =
| Density =
| Density =
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| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| Autoignition = }}
| AutoignitionPt = }}
}}
}}
'''2C-T-21''' is a [[psychedelic]] [[phenethylamine]] of the [[2C's|2C family]]. It was first synthesized by [[Alexander Shulgin]], sometimes used as an [[entheogen]]. It was the first psychedelic drug known to contain six different [[chemical element]]s in the structure.


'''2C-T-21''' ('''4-(2-fluoroethylthio)-2,5-dimethoxyphenethylamine''') is a [[psychedelic drug|psychedelic]] [[phenethylamine]] of the [[2C (psychedelics)|2C family]] sometimes used as an [[entheogen]]. It was first synthesized by [[Alexander Shulgin]].
==Chemistry==

The full name of 2C-T-21 is 4-(2-[[fluoro]][[ethyl group|ethyl]][[Thio-|thio]])-2,5-di[[methoxy]][[phenethylamine]].


==Dosage==
==Dosage==


In his book ''[[PiHKAL|PiHKAL (Phenethylamines i Have Known And Loved)]]'', Shulgin lists the dosage range as 8–12&nbsp;mg.<ref>{{CitePiHKAL}}</ref>
In his book ''[[PiHKAL|PiHKAL (Phenethylamines i Have Known And Loved)]]'', Shulgin lists the dosage range as 8–12&nbsp;mg.<ref name=pihkal>{{Cite book | author = Alexander Shulgin | title = PiHKAL | url = http://www.erowid.org/library/books_online/pihkal/pihkal049.shtml | chapter = 2C-T-21 }}</ref>


==Effects==
==Effects==


2C-T-21 is generally taken orally, and effects typically last 7 to 14 hours. The potential psychotherapeutic applications of this chemical were explored by [[Myron Stolaroff]] who found it a very promising substance in his experiments.
2C-T-21 is generally taken orally and effects typically last 7 to 10 hours.<ref name=pihkal/> The potential psychotherapeutic applications of this chemical were explored by [[Myron Stolaroff]].{{citation needed|date=May 2019}}


==Pharmacology==
==Pharmacology==


The mechanism that produces 2C-T-21’s hallucinogenic and entheogenic effects has not been specifically established, however it is most likely to result from action as a [[5-HT2A receptor|5-HT<sub>2A</sub>]] [[5-HT receptor|serotonin receptor]] [[agonist]] in the brain, a mechanism of action shared by all of the hallucinogenic tryptamines and phenethylamines for which the mechanism of action is known. Based on the relatively high potency of 2C-T-21, it is likely that this compound binds quite strongly to the 5HT<sub>2A</sub> receptor target.
The mechanism that produces 2C-T-21's hallucinogenic and entheogenic effects has not been established; however, it may result from action as a [[5-HT2A receptor|5-HT<sub>2A</sub>]] [[5-HT receptor|serotonin receptor]] [[agonist]] in the brain, a mechanism of action shared by all of the hallucinogenic tryptamines and phenethylamines for which the mechanism of action is known.

Because 2C-T-7, a related drug, has been shown to be a moderate [[monoamine oxidase]]-A inhibitor, 2C-T-21&nbsp;may likewise have MAO-A inhibitory effects. This could indicate 2C-T-21 is more likely to induce [[serotonin syndrome]] than other serotonergic hallucinogens, as at high doses it may slow the degradation of [[serotonin]], a potentially life-threatening condition.<ref>{{cite journal|last=Gallardo-Godoy|first=A|coauthors=Fierro A, McLean TH, Castillo M, Cassels BK, Reyes-Parada M, Nichols DE.|title=Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling|journal=Journal of Medicinal Chemistry|date=April 7, 2005|volume=48|issue=7|pages=2407–19|doi=10.1021/jm0493109|pmid=15801832}}</ref>

Fluoroacetate is produced by S-dealkylation of 2C-T-21.

Overdose with 2C-T-21 has been responsible for at least one fatality, so it is likely that this drug is a relatively strong MAO-A inhibitor in addition to its action as a 5HT<sub>2A</sub> agonist.{{Citation needed|date=October 2009}}


==Dangers==
==Dangers==


On March 9, 2004, a 22-year-old [[quadriplegic]] man named James Edwards Downs in St. Francisville, Louisiana, consumed an unknown dose of 2C-T-21 by sticking his tongue into a vial of powder he had purchased online. He developed a temperature of 108 degrees Fahrenheit (42 degrees Celsius),<ref name="urlNews from DEA, News Releases, 07/22/04">{{cite web |url=http://www.dea.gov/pubs/pressrel/pr072204.html |title=News from DEA, News Releases, 07/22/04 |work= |accessdate=}}</ref> had a [[tonic-clonic seizure]], and slipped into a coma. Four days later, on March 13, Downs died at Lane Memorial Hospital in Zachary, LA.{{Citation needed|date=December 2007}}
On March 9, 2004, a 22-year-old [[quadriplegic]] man named James Edwards Downs in St. Francisville, Louisiana, consumed an unknown dose of 2C-T-21 by sticking his tongue into a vial of powder he had purchased online. He developed a temperature of {{convert|108|F|C}},<ref name="urlNews from DEA, News Releases, 07/22/04">{{cite web |url=http://www.dea.gov/pubs/pressrel/pr072204.html |title=News from DEA, News Releases, 07/22/04 |archive-url=https://web.archive.org/web/20080208165133/http://www.dea.gov/pubs/pressrel/pr072204.html |archive-date=February 8, 2008 |url-status=dead }}</ref> had a [[tonic-clonic seizure]], and slipped into a coma. Four days later, on March 13, Downs died at Lane Memorial Hospital in Zachary, LA.{{Citation needed|date=December 2007}}


This death became part of a two year DEA investigation called [[Operation Web Tryp]] which was launched in 2002. On July 22, 2004, the owners of American Chemical Supply were arrested on federal charges relating to distribution of [[Federal Analog Act|controlled substance analogues]] and the death of James Edwards Downs. Little is known about the toxicity of 2C-T-21 beyond this incident.
This death became part of a two-year DEA investigation called [[Operation Web Tryp]] which was launched in 2002. On July 22, 2004, the owners of American Chemical Supply were arrested on federal charges relating to distribution of [[Federal Analog Act|controlled substance analogues]] and the death of James Edwards Downs. Little is known about the toxicity of 2C-T-21 beyond this incident.


==Legality==
==Legality==


2C-T-21 is unscheduled and uncontrolled in the United States, but possession and sales of 2C-T-21 would probably be prosecuted under the [[Federal Analog Act]] because of its structural similarities to [[2C-T-7]] and its known potential to cause death. In the wake of [[Operation Web Tryp]] in July 2004, at least one "research chemical" distributor faced charges as a consequence of the death of James Downs from 2C-T-21 overdose.
2C-T-21 is unscheduled and uncontrolled in the United States, but possession and sales of 2C-T-21 would probably be prosecuted under the [[Federal Analog Act]] because of its structural similarities to [[2C-T-7]] and its known potential to cause death. In the wake of [[Operation Web Tryp]] in July 2004, at least one distributor faced charges as a consequence of the death of James Downs from 2C-T-21 overdose.

===Canada===
As of October 31, 2016, 2C-T-21 is a controlled substance (Schedule III) in Canada.<ref>[http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)]</ref>


==References==
==References==
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==External links==
==External links==
* [http://www.erowid.org/library/books_online/pihkal/pihkal049.shtml 2C-T-21 Entry in PiHKAL]
* [http://pihkal.info/read.php?domain=pk&id=49 2C-T-21 Entry in PiHKAL • info]
* [http://www.erowid.org/chemicals/2ct21/ Erowid 2C-T-21 Vault]
* [http://www.erowid.org/chemicals/2ct21/ Erowid 2C-T-21 Vault]


{{2C's}}
{{2Cs}}
{{Hallucinogenic phenethylamines}}
{{Hallucinogenic phenethylamines}}
{{Serotonergics}}
{{Serotonergics}}
{{PiHKAL}}
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{{Use mdy dates|date=August 2010}}


{{DEFAULTSORT:2c-T-21}}
{{DEFAULTSORT:2c-T-21}}
[[Category:2C (psychedelics)]]
[[Category:2C (psychedelics)]]
[[Category:Monoamine oxidase inhibitors]]
[[Category:Thioethers]]
[[Category:Thioethers]]
[[Category:Organofluorides]]
[[Category:Fluoroethyl compounds]]
[[Category:Phenol ethers]]
[[Category:Designer drugs]]

[[fa:۲سی-تی-۲۱]]
[[pl:2C-T-21]]

Latest revision as of 17:56, 29 November 2023

2C-T-21
Names
Preferred IUPAC name
2-{4-[(2-Fluoroethyl)sulfanyl]-2,5-dimethoxyphenyl}ethan-1-amine
Other names
4-(2-Fluoroethylthio)-2,5-dimethoxyphenethylamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C12H18FNO2S/c1-15-10-8-12(17-6-4-13)11(16-2)7-9(10)3-5-14/h7-8H,3-6,14H2,1-2H3 checkY
    Key: ZBUUUKBTOCTOPW-UHFFFAOYSA-N checkY
  • InChI=1/C12H18FNO2S/c1-15-10-8-12(17-6-4-13)11(16-2)7-9(10)3-5-14/h7-8H,3-6,14H2,1-2H3
    Key: ZBUUUKBTOCTOPW-UHFFFAOYAH
  • COc1cc(SCCF)c(cc1CCN)OC
Properties
C12H18FNO2S
Molar mass 259.34 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

2C-T-21 (4-(2-fluoroethylthio)-2,5-dimethoxyphenethylamine) is a psychedelic phenethylamine of the 2C family sometimes used as an entheogen. It was first synthesized by Alexander Shulgin.

Dosage

[edit]

In his book PiHKAL (Phenethylamines i Have Known And Loved), Shulgin lists the dosage range as 8–12 mg.[1]

Effects

[edit]

2C-T-21 is generally taken orally and effects typically last 7 to 10 hours.[1] The potential psychotherapeutic applications of this chemical were explored by Myron Stolaroff.[citation needed]

Pharmacology

[edit]

The mechanism that produces 2C-T-21's hallucinogenic and entheogenic effects has not been established; however, it may result from action as a 5-HT2A serotonin receptor agonist in the brain, a mechanism of action shared by all of the hallucinogenic tryptamines and phenethylamines for which the mechanism of action is known.

Dangers

[edit]

On March 9, 2004, a 22-year-old quadriplegic man named James Edwards Downs in St. Francisville, Louisiana, consumed an unknown dose of 2C-T-21 by sticking his tongue into a vial of powder he had purchased online. He developed a temperature of 108 °F (42 °C),[2] had a tonic-clonic seizure, and slipped into a coma. Four days later, on March 13, Downs died at Lane Memorial Hospital in Zachary, LA.[citation needed]

This death became part of a two-year DEA investigation called Operation Web Tryp which was launched in 2002. On July 22, 2004, the owners of American Chemical Supply were arrested on federal charges relating to distribution of controlled substance analogues and the death of James Edwards Downs. Little is known about the toxicity of 2C-T-21 beyond this incident.

Legality

[edit]

2C-T-21 is unscheduled and uncontrolled in the United States, but possession and sales of 2C-T-21 would probably be prosecuted under the Federal Analog Act because of its structural similarities to 2C-T-7 and its known potential to cause death. In the wake of Operation Web Tryp in July 2004, at least one distributor faced charges as a consequence of the death of James Downs from 2C-T-21 overdose.

Canada

[edit]

As of October 31, 2016, 2C-T-21 is a controlled substance (Schedule III) in Canada.[3]

References

[edit]
  1. ^ a b Alexander Shulgin. "2C-T-21". PiHKAL.
  2. ^ "News from DEA, News Releases, 07/22/04". Archived from the original on February 8, 2008.
  3. ^ Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)
[edit]
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