View source for 2C-T-21

{{chembox
| ImageFile1 = 2CT21.svg
| ImageSize1 = 200px
| ImageFile2 = 2C-T-21-3d-sticks.png
| ImageSize2 = 200px
| IUPACName = 2-[2,5-Dimethoxy-4-(2-fluoroethylthio)phenyl]ethanamine
| OtherNames =
| Section1 = {{Chembox Identifiers
| ChemSpiderID = 21106231
| 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
| InChIKey = ZBUUUKBTOCTOPW-UHFFFAOYAH
| CASNo = 207740-33-8
| PubChem =
| SMILES = COc1cc(SCCF)c(cc1CCN)OC
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>12</sub>H<sub>18</sub>FNO<sub>2</sub>S
| MolarMass = 259.34 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility = }}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| Autoignition = }}
}}
'''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.

==Chemistry==

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

==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>

==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.

==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.

As the 2,5-desmethoxy derivative of 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>

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==

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}}

This death became part of a two year DEA investigation called [[Operation Web Tryp]] which was launched in 2002 following the death of a New York man who had taken unspecified chemicals purchased from David Linder (aka Pondman or Dr. Benway, the latter a reference to a character created by [[William S. Burroughs]]). 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==

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.

==References==
{{Reflist}}

==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]

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

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

[[pl:2C-T-21]]
[[Category:2Fix]]