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2C-T-21: Difference between revisions

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'''2,5-Dimethoxy-4-ethylfluorothiophenethylamine''' (also known as '''2C-T-21''', or colloquially as '''Aurora''') is a [[psychoactive class::psychedelic]] substance of the [[chemical class::phenethylamine]] chemical class that produces [[psychedelic]] effects when [[administered]]. It is a member of the [[2C-x family]] of psychedelic phenethylamines, all of which were derived from the systematic modification of the [[mescaline]] molecule.


'''2C-T-21''' is a [[psychedelic drug|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 was first synthesized by [[Alexander Shulgin]] and documented in his book [[PiHKAL]] ("Phenethylamines I Have Known and Loved"). The dosage range is listed as 8–12 mg. It is described in various reports as being generally relaxed and clear-headed with mild visual effects.<ref name="PiHKAL">{{cite book|title=PiHKAL: A Chemical Love Story|title-link=PiHKAL|author-link1=Alexander Shulgin|author1=Alexander Shulgin|author2=Ann Shulgin|year=1991|publisher=Transform Press|location=United States|isbn=0963009605|oclc=1166889264|chapter-url=https://erowid.org/library/books_online/pihkal/pihkal049.shtml|chapter=#49. 2C-T-21}}</ref> In ''Thanatos To Eros, 35 Years of Psychedelic Exploration'', Myron Stolaroff describes it as "not psychedelic, but a wonderful energizer", along with displaying a notable lack of [[appetite suppression]] typically observed with members of its class. However he also mentions concerns regarding toxicity.<ref name=":0">{{cite web|url=http://www.maps.org/index.php?option=com_content&view=article&id=5406|title=Thanatos To Eros, 35 Years of Psychedelic Exploration|author=Myron J. Stolaroff|year=1994|publisher=Multidisciplinary Association for Psychedelic Studies (MAPS)}}</ref>
 
In March 2004, a 22-year-old American male died after ingesting an unknown amount of 2C-T-21. This death became part of a two-year DEA investigation called "Operation Web Tryp" which ended with the arrests of 10 persons involved in the online distribution of [[research chemicals]].<ref name="DEAnews">{{cite web|url=https://www.dea.gov/pubs/pressrel/pr072204.html|archive-url=https://web.archive.org/web/20171022211020/https://www.dea.gov/pubs/pressrel/pr072204.html|archive-date=October 22, 2017|title=DEA Announces Arrests Of Website: Operators Selling Illegal Designer Drugs|date=July 22, 2004|publisher=Drug Enforcement Administration (DEA)}}</ref> 2C-T-21 remains unscheduled in the United States.
 
Very little data exists about the pharmacological properties, metabolism, and toxicity of 2C-T-21, although a paper by Daniel Trachsel hypothesizes that one of its metabolites is the poison [https://en.wikipedia.org/wiki/Fluoroacetate fluoroacetate].<ref name=":1">Trachsel, Daniel. (2012) [https://pubmed.ncbi.nlm.nih.gov/22374819 Fluorine in psychedelic phenethylamines], ''Drug Testing and Analysis'', Vol. 4, Issue 7-8 (Special Issue: Psychedelic Substances), July-August 2012, pp. 577-590. [https://doi.org/10.1002/dta.413 DOI:10.1002/dta.413]</ref> It has little history of human usage. It is strongly advised to use [[harm reduction practices]] if using this substance.


==Chemistry==
==Chemistry==
2C-T-21, or 2,5-dimethoxy-4-ethylfluorothiophenethylamine, is a [[substituted phenethylamine]] featuring a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain. 2C-T-21 contain methoxy functional groups CH<sub>3</sub>O- attached to carbons R<sub>2</sub> and R<sub>5</sub> of the benzene ring as well as an ethylfluoro thioether group attached to carbon R<sub>4</sub> of the phenyl ring.
2C-T-21 belongs to the 2C family of phenethylamines, all of which contain methoxy groups on the 2 and 5 positions of the benzene ring.
==Pharmacology==
{{pharmacology}}
2C-T-21's [[psychedelic]] effects are believed to come from its efficacy at the [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] as a [[Agonist#Agonists|partial agonist]]. However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive.
This compound, being similar in structure to [[2C-T-2]] and [[2C-T-7]] is also believed to potentially have [[MAOI]] properties.
==Subjective effects==
{{effectStub}}
{{Preamble/SubjectiveEffects}}
{{effects/base
|{{effects/physical|
*'''[[Effect::Stimulation]]''' - In terms of its effects on the physical energy levels of the user, 2C-T-21 is generally considered to be energetic and stimulating in a fashion is comparable to that of other [[phenethylamines]] such as [[2C-B]], [[2C-E]] and [[2C-P]]. However, at certain doses and contexts, it may produce periods of notable [[sedation]].
*'''[[Effect::Spontaneous physical sensations]]''' - The "body high" of 2C-T-21 is intense, but in comparison to [[2C-E]] or [[2C-B]], it can be considered mild though is still capable of becoming very powerful and highly physically euphoric. The sensation itself can be described as intense and will manifest itself in the form of a continuously shifting tingling sensation that travels up and down the body in spontaneous waves. 
*'''[[Effect::Bodily control enhancement]]'''
*'''[[Effect::Changes in felt bodily form]]'''
*'''[[Effect::Tactile enhancement]]'''
*'''[[Effect::Temperature regulation suppression]]'''
**'''[[Effect::Increased bodily temperature]]'''
*'''[[Effect::Abnormal heartbeat]]'''{{citation needed}}
*'''[[Effect::Increased blood pressure]]'''{{citation needed}}
*'''[[Effect::Increased heart rate]]'''{{citation needed}}
*'''[[Effect::Dehydration]]'''
*'''[[Effect::Diarrhea]]'''
*'''[[Effect::Difficulty urinating]]''' or [[Effect::Frequent urination]]
*'''[[Effect::Dizziness]]'''
*'''[[Effect::Headaches]]'''
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Muscle contractions]]'''
*'''[[Effect::Muscle spasms]]'''
*'''[[Effect::Muscle cramps]]'''
*'''[[Effect::Nausea]]''' -  Mild to extreme nausea is commonly reported when consumed in moderate to high dosages, and either passes once the user has vomited or gradually fades by itself as the peak sets in.
*'''[[Effect::Stomach bloating]]'''
*'''[[Effect::Stomach cramps]]'''
*'''[[Effect::Teeth grinding]]'''
*'''[[Effect::Excessive yawning]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Watery eyes]]'''
}}
{{effects/visual|
====[[Visual effects - Psychedelics#Enhancements|Enhancements]]====
*'''[[Effect::Visual acuity enhancement]]'''
*'''[[Effect::Colour enhancement]]'''
*'''[[Effect::Pattern recognition enhancement]]'''
====[[Visual effects - Psychedelics#Distortions|Distortions]]====
*'''[[Effect::Visual drifting|Drifting]]''' ''([[Visual drifting#Melting|melting]], [[Visual drifting#Flowing|flowing]], [[Visual drifting#Breathing|breathing]] and [[Visual drifting# morphing|morphing]])'' - In comparison to other psychedelics, this effect can be described as highly detailed, slow and smooth in motion, static in appearance. <!-- and extremely realistic in style but with a subtle digital/cartoonish form. -->
*'''[[Effect::Tracers]]'''
*'''[[Effect::After images]]'''
*'''[[Effect::Symmetrical texture repetition]]'''
*'''[[Effect::Colour shifting]]'''
====[[Effect::Geometry]]====
The visual geometry that is present throughout this trip can be described as more similar in appearance to that of [[psilocin]] than that of [[LSD]]. <!--
They can be comprehensively described as structured in their organization, organic in geometric style, intricate in complexity, large, fast and smooth in motion, colorful in scheme, glossy in color, sharp in their edges and equally rounded and angular in their corners. It gives off a contradictory natural and synthetic feel with slightly more mystical and shamanic undertones in comparison to other [[phenethylamines]]. At higher dosages, they are equally likely to result in states of [[Effect::8A Geometry|Level 8A]] visual geometry or [[Effect::8B Geometry|Level 8B]]. -->
====Hallucinatory states====
<!-- 2C-T-7 produces a full range of high level hallucinatory states in a fashion that is more consistent and reproducible than that of many other commonly used psychedelics. This holds particularly true in comparison to other substances within the [[phenethylamines|phenethylamine]] family. These effects include: -->
*'''[[Effect::Transformations]]'''
*'''[[Effect::Internal hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'')<!-- - This effect is very consistent in dark environments at appropriately high dosages. They can be comprehensively described through their [[Visual_effects:_Internal_hallucinations#Variations|variations]] as lucid in believability, interactive in style, new experiences in content, autonomous in controllability, [[Geometry|geometry]]-based in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme. -->
}}
|{{effects/cognitive|
The head space of 2C-T-21 is described by many as one which is both insightful and relatively normal in its thought processes even at moderate to high dosages.


The full name of 2C-T-21 is '''4-(2-[[fluoro]][[ethyl group|ethyl]][[Thio-|thio]])-2,5-di[[methoxy]][[phenethylamine]]'''.
*'''[[Effect::Emotion enhancement]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Novelty enhancement]]'''
*'''[[Effect::Time distortion]]'''
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Analysis enhancement]]''' - 2C-T-21 is notable for providing an unusual sense of [[outrospection]].
*'''[[Effect::Personal bias suppression]]'''
*'''[[Effect::Conceptual thinking]]'''
*'''[[Effect::Memory suppression]]'''
**'''[[Effect::Ego death]]'''
*'''[[Effect::Immersion enhancement]]'''
*'''[[Effect::Thought loops]]'''
*'''[[Effect::Delusion]]'''
*'''[[Effect::Wakefulness]]'''


==Dosage==
}}
{{effects/auditory|
*'''[[Effect::Auditory enhancement|Enhancements]]'''
*'''[[Effect::Auditory distortion|Distortions]]'''


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/transpersonal|
*'''[[Effect::Unity and interconnectedness]]'''


==Effects==
}}
}}
===Experience reports===
There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here:


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.
*[https://www.erowid.org/experiences/subs/exp_2CT21.shtml Erowid Experience Vaults: 2C-T-21]


==Pharmacology==
==Toxicity and harm potential==
{{toxicity}}
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}}
On March 9, 2004, a 22-year-old American male 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="DEAnews" /> had a tonic-clonic seizure, and slipped into a coma before dying four days later.{{Citation needed|date=December 2007}} These symptoms are consistent with those seen in fluoroacetate poisoning, for which there is no known effective antidote.<ref>Proudfoot et al. (2006) [https://link.springer.com/article/10.2165/00139709-200625040-00002 Sodium Fluoroacetate Poisoning] . ''Toxicological Review''s, '''25''' pp. 213–219.</ref>
 
Fluoroacetate is hypothesized to be a metabolite of 2C-T-21.<ref name=":1" /> Sub-lethal doses of fluoroacetate take up to four days to clear from the body.<ref>Eason et al. (1993) [https://books.google.ie/books?id=ACI4AAAAIAAJ&pg=PA330&redir_esc=y#v=onepage&q&f=false Sodium monofluoroacetate and alternative toxins for possum control], ''New Zealand Journal of Zoology'', Vol. 20, Issue 4, pp. 329-334. [https://doi.org/10.1080/03014223.1993.10420354 DOI:10.1080/03014223.1993.10420354] </ref> As such, it is likely dangerous to take 2C-T-21 multiple days in a row as this poisonous metabolite will accumulate. Furthermore, sub-lethal doses may cause damage to tissue with high energy needs (e.g. the brain, gonads, heart, lungs, and fetus). This may account for the experience of a couple who became "convinced that it is toxic" in Stolaroff's book.<ref name=":0" />
 
There is no anecdotal evidence to suggest that a single, moderate dose of 2C-T-21 can cause negative health effects, although nothing can be guaranteed.
 
It is strongly discouraged to administer 2C-T-21 non-orally because this may cause vomiting, numerous negative side effects, or death at high doses.


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.
It is strongly recommended that one use [[responsible drug use|harm reduction practices]], such as [[volumetric dosing]], when using this substance to ensure the accurate administration of the intended dose.


Fluoroacetate is produced by S-dealkylation of 2C-T-21.
===Tolerance and addiction potential===
2C-T-21 is [[Addiction potential::not habit-forming]] and the desire to use it can actually decrease with use. It is most often self-regulating.  


==Dangers==
Tolerance to the effects of 2C-T-21 is built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7 days]] to be back at baseline (in the absence of further consumption). 2C-T-21 presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of 2C-T-21 all psychedelics will have a reduced effect.


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}}
===Dangerous interactions===
{{DangerousInteractions/Intro}}


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.
If 2C-T-21 does have [[MAOI]] effects as commonly speculated, this could indicate that 2C-T-21 is more likely to induce [[serotonin syndrome]] or general [[neurotransmitter]] overload (especially at high dosages) than other [[serotonergic psychedelic]]s.<ref>{{cite journal|title=Sulfur-Substituted α-Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors:  Biological Activities, CoMFA Analysis, and Active Site Modeling|doi=10.1021/jm0493109|pmid=15801832|url=http://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.689.281&rep=rep1&type=pdf|first1=A.|last1=Gallardo-Godoy|first2=A.|last2=Fierro|first3=T. H.|last3=McLean|first4=M.|last4=Castillo|first5=B. K.|last5=Cassels|first6=M.|last6=Reyes-Parada|first7=D. E.|last7=Nichols|author-link7=David E. Nichols|year=2005|volume=48|issue=7|pages=2407–2419|journal=Journal of Medicinal Chemistry|issn=0022-2623|eissn=1520-4804|oclc=39480771}}</ref> This may make it dangerous to combine it with other [[MAOI]]s, [[stimulant]]s and certain substances which releases neurotransmitters such as [[serotonin]] or [[dopamine]]. These substances include but are not limited to:
{|
|-
|
*'''[[5-MeO-MiPT]]'''
*'''[[2C-T-2]]'''
*'''[[2C-T-7]]'''
*'''[[AMT]]'''
*'''[[Ayahuasca]]'''
*'''[[Harmala alkaloids]]'''
*'''[[2-AI]]'''
*'''[[2-FMA]]'''
*'''[[3-FPM]]'''
*'''[[4-FA]]'''
*'''[[A-PVP]]'''
*'''[[Amphetamine]]'''
*'''[[Cocaine]]'''
*'''[[Ethylphenidate]]'''
||
*'''[[N-Methylbisfluoromodafinil]]'''
*'''[[Isopropylphenidate]]'''
*'''[[MDAI]]'''
*'''[[MDMA]]'''
*'''[[Mephedrone]]'''
*'''[[Methamphetamine]]'''
*'''[[Methiopropamine]]'''
*'''[[Methylone]]'''
*'''[[Methylphenidate]]'''
*'''[[Modafinil]]'''
*'''[[Nicotine]]'''
*'''[[NM-2-AI]]'''
*'''[[Noopept]]'''
|}


==Legality==
==Legal status==
{{LegalStub}}


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.
*'''Austria''': 2C-T-21 is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).{{citation needed}}
*'''Canada''': As of October 31st, 2016; 2C-T-21 is a controlled substance (Schedule III) in Canada.<ref>{{cite journal|url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php|title=Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)|id=SOR/2016-72|issn=0045-4206|work=Canada Gazette Part II|volume=150|issue=9|publication-date=May 4, 2016|date=April 15, 2016|}}</ref>
*'''Germany''': 2C-T-21 is controlled under the NpSG<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/anlage.html|title=Anlage NpSG|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> (''New Psychoactive Substances Act'') as of November 26, 2016.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl116s2615.pdf|title=Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe|pages=2615-2622|issn=0341-1095|oclc=1004462279|publisher=Bundesanzeiger Verlag|date=November 21, 2016|publication-date=November 25, 2016|language=de|work=Bundesgesetzblatt Jahrgang 2016 Teil I Nr. 55}}</ref> Production and import with the aim to place it on the market, administration to another person, placing it on the market and trading is punishable. Possession is illegal but not punishable.<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__4.html|title=§ 4 NpSG|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref><ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__3.html|title=§ 3 NpSG|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> The legislator considers it possible that orders of 2C-T-21 are punishable as an incitement to place it on the market.<ref>{{cite web|url=http://dip21.bundestag.de/dip21/btd/18/085/1808579.pdf|title=Gesetzentwurf der Bundesregierung: Entwurf eines Gesetzes zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe|page=20|date=May 30, 2016|id=Drucksache 18/8579|publisher=Deutscher Bundestag|language=de}}</ref>
*'''Switzerland''': 2C-T-21 can be considered a controlled substance as a defined derivative of Phenethylamine under Verzeichnis E point 130. It is legal when used for scientific or industrial use.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>
*'''United Kingdom''': 2C-T-21 is a Class A drug in the United Kingdom as a result of the phenethylamine catch-all clause.<ref>{{cite web|title=Schedule 2: Part I: Class A Drugs|url=http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I|work="Misuse of Drugs Act 1971"|access-date=August 20, 2020|publisher=UK Government}}</ref>
*'''United States''': 2C-T-21 is technically not scheduled in the United States, but could be considered an analogue of 2C-T or 2C-T-7 and may therefore be considered a Schedule I drug under the Federal Analogue Act.{{citation needed}}


===Canada===
==See also==
As of October 31st, 2016; 2C-T-21 is a controlled substance (Schedule III) in Canada. http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php


==References==
*[[Responsible use]]
{{Reflist}}
**[[Volumetric dosing]]
*[[Research chemical]]
*[[MAOI]]
*[[2C-x]]
*[[2C-T-7]]
*[[2C-E]]


==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]


{{2C's}}
*[https://en.wikipedia.org/wiki/2C-T-21 2C-T-21 (Wikipedia)]
{{Hallucinogenic phenethylamines}}
*[https://erowid.org/chemicals/2ct21/ 2C-T-21 (Erowid Vault)]
{{Serotonergics}}
*[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=49 2C-T-21 (PiHKAL / Isomer Design)]
{{PiHKAL}}
 
==References==
<references />


{{DEFAULTSORT:2c-T-21}}
[[Category:Psychoactive substance]]
[[Category:2C (psychedelics)]]
[[Category:Psychedelic]]
[[Category:Thioethers]]
[[Category:2C-T-x]]
[[Category:Organofluorides]]
[[Category:Research chemical]]
[[Category:Phenol ethers]]
[[Category:Designer drugs]]
Retrieved from "http://psy.st/wiki/2C-T-21"