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2C-T-2: Difference between revisions
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{{SubstanceBox/2C-T-2}} | {{SubstanceBox/2C-T-2}} | ||
'''2,5-Dimethoxy-4-ethylthiophenethylamine''' (also known as '''2C-T-2''', and '''Rosy''') is a [[Psychoactive class::psychedelic]] [[ | '''2,5-Dimethoxy-4-ethylthiophenethylamine''' (also known as '''2C-T-2''', and '''Rosy''') is a [[Psychoactive class::psychedelic]] substance of the [[chemical class::phenethylamine]] chemical class that produces psychedelic effects when [[Route of administration|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-2 was first synthesized and tested for activity in humans by [[Alexander Shulgin]] in 1981<ref name="Shulgin1982">{{cite book|author=Alexander Shulgin|author-link=Alexander Shulgin|title=Pharmacology Notes IV (The Shulgin Lab Books)|publisher=Erowid|url=https://erowid.org/library/books_online/shulgin_labbooks/shulgin_pharmacology_notebook4_searchable.pdf|page=474|place=Lafayette, CA, USA|year=1982}}</ref> and described in his 1991 book [[PiHKAL]] ("Phenethylamines I Have Known and Loved").<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/pihkal040.shtml|chapter=#40. 2C-T-2}}</ref> It is a member of the so-called "magical half-dozen" which refers to Shulgin's self-rated most important [[phenethylamine]]-derived compounds, all of which except [[mescaline]] he developed and synthesized himself. They are found within the first book of [[PiHKAL]], and are as follows: [[mescaline]], [[DOM]], [[2C-B]], 2C-E, [[2C-T-2]] and [[2C-T-7]].<ref>{{cite book|title=PiHKAL: A Chemical Love Story|author-link1=Alexander Shulgin|author1=Alexander Shulgin|author2=Ann Shulgin|year=1991|publisher=Transform Press|location=United States|isbn=0963009605|oclc=1166889264|url=https://erowid.org/library/books_online/pihkal/pihkal.shtml}}</ref> | |||
Anecdotal reports | Anecdotal reports generally characterize 2C-T-2 as a highly dose sensitive psychedelic known for its open headspace and unpredictable [[body load]]. | ||
Very little data exists about the pharmacological properties, metabolism, and toxicity of 2C-T-2, and it has a relatively short history of human usage. Many reports also indicate that its physical effects may be too severe for those who are not already experienced with [[psychedelics]] or suffer from pre-existing physical conditions. It is highly advised to approach this [[hallucinogenic]] substance with the proper amount of precaution and [[harm reduction practices]] if using it. | |||
Very little data exists about the pharmacological properties, metabolism, and toxicity of 2C-T-2, and it has | |||
==History and culture== | ==History and culture== | ||
{{historyStub}} | {{historyStub}} | ||
Following the initial positive results found by Shulgin's research group, a more formal study was carried out by psychedelic psychotherapy pioneer Myron J. Stolaroff who was interested in evaluating the potential use of 2C-T-2 in psychotherapy.<ref>{{cite book|last1=Stolaroff|first1=M. J.|last2=Wells|first2=C.|chapter=Preliminary results with new psychoactive agents 2C-T-2 and 2C-T-7|title=Jahrbuch für Ethnomedizin und Bewußtseinsforschung|trans-title=Yearbook of Ethnomedicine and the Study of Consciousness|editor-last1=Rätsch|editor-first1=C.|editor-last2=Baker|editor-first2=J.|year=1993|volume=2|pages=99–117|publisher=Multidisciplinary Association for Psychedelic Studies (MAPS)|chapter-url=http://www.maps.org/images/pdf/1993_stolaroff_1.pdf}}</ref> Based on the experiences of forty participants in the study who took 2C-T-2, Stolaroff compared the effects favorably to [[MDMA]], describing it as more emotionally opening and permitting a wider exploration of feelings and thoughts. | |||
==Chemistry== | ==Chemistry== | ||
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2C-T-2, or 2,5-dimethoxy-4-ethylthiophenethylamine, is a substituted [[phenethylamines|phenethylamine]] featuring a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain. 2C-T-2 belongs to the 2C family of phenethylamines which 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. 2C-T-2 is also substituted at R<sub>4</sub> with an ethyl thioether group. | 2C-T-2, or 2,5-dimethoxy-4-ethylthiophenethylamine, is a substituted [[phenethylamines|phenethylamine]] featuring a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain. 2C-T-2 belongs to the 2C family of phenethylamines which 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. 2C-T-2 is also substituted at R<sub>4</sub> with an ethyl thioether group. | ||
2C-T-2 is a close structural analogue of [[2C-T-7]]; the two differ by the length of the alkane chain in their thioether functional group.<ref | 2C-T-2 is a close structural analogue of [[2C-T-7]]; the two differ by the length of the alkane chain in their thioether functional group.<ref name ="PiHKAL"/> | ||
==Pharmacology== | ==Pharmacology== | ||
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The mechanism of action that produces 2C-T-2’s [[hallucinogenic]] and [[entheogen]]ic effects has not been established in scientific literature; however, its primary psychedelic effects are more than likely a result of its efficacy at the [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] as a [[Agonist#Agonists|partial agonist]]. This mechanism of action is shared by many other psychedelic [[phenethylamine]]s and [[tryptamine]]s. | The mechanism of action that produces 2C-T-2’s [[hallucinogenic]] and [[entheogen]]ic effects has not been established in scientific literature; however, its primary psychedelic effects are more than likely a result of its efficacy at the [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] as a [[Agonist#Agonists|partial agonist]]. This mechanism of action is shared by many other psychedelic [[phenethylamine]]s and [[tryptamine]]s. | ||
Athough no established scientific experiments have been performed to establish MAO-A inhibition of 2C-T-2, phenethylamine derivatives substituted with an alkylthio group at the 4 position ( | Athough no established scientific experiments have been performed to establish MAO-A inhibition of 2C-T-2, phenethylamine derivatives substituted with an alkylthio group at the 4 position (4-MTA, and the 2,5-desmethoxy derivative of [[2C-T-7]]) are known to act as selective [[MAOI|monoamine oxidase A inhibitors]].{{citation needed}} Furthermore, many compounds of the amphetamine-analogs of the [[2C-T-x]] have been found to have highly selective MAO-A inhibition<ref name="Gallardo-Godoy2005">{{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|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|url=http://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.689.281&rep=rep1&type=pdf}}</ref>. Therefore, this substance may likewise have [[MAOI]] effects.<ref>{{cite journal|title=Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)|first1=D. S.|last1=Theobald|first2=H. H.|last2=Maurer|pmid=17067556|doi=10.1016/j.bcp.2006.09.022|journal=Biochemical Pharmacology|volume=73|issue=2|year=2007|pages=287-297|issn=0006-2952|eissn=1873-2968|oclc=01536391}}</ref> | ||
However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive. | However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive. | ||
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{{effects/base | {{effects/base | ||
|{{effects/physical| | |{{effects/physical| | ||
*'''[[Effect::Spontaneous | *'''[[Effect::Stimulation]]''' - 2C-T-2 is usually considered to be very energetic and stimulating in a fashion that is quite comparable to that of other [[phenethylamines]] such as [[2C-B]], [[2C-E]] and [[2C-P]]. | ||
*'''[[Effect::Spontaneous physical sensations]]''' - The "body high" of 2C-T-2 can be described as very intense and uncomfortable in comparison to [[2C-E]] or [[2C-B]]. In high doses, it's capable of causing painful cramping. It is similar yet distinct from the "body high" experienced on [[2C-T-7]], but is considered much more unpleasant. The sensation itself can be described as intense and may 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]]''' - Although this component is capable of manifesting itself in a distinct and noticeable fashion for most users, it does not generally seem to be as apparent or intense as the same component found within [[LSD]] and [[2C-B]]. | *'''[[Effect::Bodily control enhancement]]''' - Although this component is capable of manifesting itself in a distinct and noticeable fashion for most users, it does not generally seem to be as apparent or intense as the same component found within [[LSD]] and [[2C-B]]. | ||
*'''[[Effect::Tactile enhancement]]''' | *'''[[Effect::Tactile enhancement]]''' | ||
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*'''[[Effect::Stomach cramps]]''' | *'''[[Effect::Stomach cramps]]''' | ||
*'''[[Effect::Vasoconstriction]]''' | *'''[[Effect::Vasoconstriction]]''' | ||
*'''[[Effect::Diarrhea]]''' | |||
*'''[[Effect::Temperature regulation suppression]]''' | *'''[[Effect::Temperature regulation suppression]]''' | ||
**'''[[Effect::Increased bodily temperature]]''' | **'''[[Effect::Increased bodily temperature]]''' | ||
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At common to high doses, 2C-T-2 is capable of producing 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]] family. These effects include: | At common to high doses, 2C-T-2 is capable of producing 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]] family. These effects include: | ||
*'''[[Effect::Transformations]]''' | *'''[[Effect::Transformations]]''' | ||
*'''[[Effect::External | *'''[[Effect::External hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'') - In comparison to other psychedelics such as [[ayahuasca]], 2C-T-2 is very high in external hallucinations. This particular effect commonly contains hallucinations with scenarios, settings, concepts and [[autonomous entity]] contact manifested as dense solidified geometric matter or physical objects of imagined concepts. They are more common within dark environments and can be described as external in their manifestation, lucid in believability, interactive in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme. | ||
*'''[[Effect::Internal | *'''[[Effect::Internal hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'') - In comparison to other psychedelics such as [[LSD]], 2C-T-2 is very high in hallucinations embedded within visual geometry. This particular effect commonly contains hallucinations with scenarios, settings, concepts and autonomous entity contact. They are more common within dark environments and can be described as internal in their manifestation, lucid in believability, interactive in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme. | ||
}} | }} | ||
|{{effects/cognitive| | |{{effects/cognitive| | ||
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*'''[[Effect::Thought acceleration]]''' | *'''[[Effect::Thought acceleration]]''' | ||
*'''[[Effect::Thought loops]]''' | *'''[[Effect::Thought loops]]''' | ||
*'''[[Effect:: | *'''[[Effect::Delusion]]''' | ||
*'''[[Effect::Wakefulness]]''' | *'''[[Effect::Wakefulness]]''' | ||
}} | }} | ||
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}} | }} | ||
}} | }} | ||
===Experience reports=== | ===Experience reports=== | ||
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==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
{{toxicity}} | |||
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}} | {{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}} | ||
The toxicity and long-term health effects of recreational 2C-T-2 use do not seem to have been studied in any scientific context and the exact toxic dosage is unknown | The toxicity and long-term health effects of recreational 2C-T-2 use do not seem to have been studied in any scientific context and the exact toxic dosage is unknown. | ||
Anecdotal reports suggest that there are [[Toxicity::no negative health effects attributed to trying this drug]], but nothing can be completely guaranteed. | |||
Tolerance to the effects of 2C-T-2 | It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance. | ||
===Dependence and abuse potential=== | |||
2C-T-2 is [[Addiction potential::not habit-forming]], and the desire to use it can actually decrease with use. It is most often self-regulating. | |||
Tolerance to the effects of 2C-T-2 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-2 presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of 2C-T-2 all psychedelics will have a reduced effect. | |||
===Dangerous interactions=== | ===Dangerous interactions=== | ||
{{DangerousInteractions/Intro}} | {{DangerousInteractions/Intro}} | ||
If 2C-T-2 does have [[MAOI]] effects as has been speculated,{{citation needed}} this could indicate that 2C-T-2 is more likely to induce [[serotonin syndrome]] or general [[neurotransmitter]] overload (especially at high dosages) than other [[serotonergic psychedelic|serotonergic psychedelics]].<ref | If 2C-T-2 does have [[MAOI]] effects as has been speculated,{{citation needed}} this could indicate that 2C-T-2 is more likely to induce [[serotonin syndrome]] or general [[neurotransmitter]] overload (especially at high dosages) than other [[serotonergic psychedelic|serotonergic psychedelics]].<ref name="Gallardo-Godoy2005"/> This may make it dangerous to combine it with other [[MAOIs]], [[stimulant]]s and certain substances which promotes the release of neurotransmitters such as [[serotonin]] or [[dopamine]]. These substances include but are not limited to: | ||
{| | {| | ||
|- | |- | ||
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|} | |} | ||
== | ==Legal status== | ||
In November 2003, the European Council decided that 2C-T-2 shall be subjected by the Member States to control measures and criminal penalties within three months.<ref>{{cite magazine|url=http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2003:321:0064:0065:EN:PDF|title=COUNCIL DECISION 2003/847/JHA|date=November 27, 2003|publication-date=December 6, 2003|work=Official Journal of the European Union|pages=64-65|id=L 321|publisher=Office for Official Publications of the European Communites|oclc=52224955}}</ref> | |||
*''' | |||
*''' | *'''Australia''': 2C-T-2 is illegal in Australia as of 2005.{{citation needed}} | ||
*'''Belgium | *'''Austria''': 2C-T-2 is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).{{citation needed}} | ||
*'''Brazil''' - | *'''Belgium''': 2C-T-2 was added to the list of illegal psychotropic substances on Nov 8, 2004.{{citation needed}} | ||
*'''Denmark | *'''Brazil''': 2C-T-2 is illegal to possess, produce and sell as it is listed on Portaria SVS/MS nº 344.<ref>{{cite web|url=http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7|title=RESOLUÇÃO DA DIRETORIA COLEGIADA - RDC N° 130, DE 2 DE DEZEMBRO DE 2016|publication-date=December 5, 2016|publisher=Agência Nacional de Vigilância Sanitária (ANVISA) [Brazilian Health Regulatory Agency (ANVISA)]|language=pt}}</ref> | ||
*''' | *'''Canada''': 2C-T-2 would be considered Schedule III as it is a derivative of 2,5-dimethoxyphenethylamine.<ref>{{cite web|url=http://isomerdesign.com/Cdsa/schedule.php?schedule=3§ion=ALL&structure=C|title=Schedule III|work=Controlled Drugs and Substances Act (CDSA)|publisher=Isomer Design|access-date=October 10, 2020}}</ref> | ||
*'''China''': As of October 2015, 2C-T-2 is a controlled substance in China.<ref>{{cite web|url=http://www.sfda.gov.cn/WS01/CL0056/130753.html|title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知|publisher=国家食品药品监督管理总局 [China Food and Drug Administration (CFDA)]|date=September 27, 2015|language=zh|archive-url=https://web.archive.org/web/20170906191704/http://www.sfda.gov.cn/WS01/CL0056/130753.html|archive-date=September 6, 2017}}</ref> | |||
*'''Italy | *'''Denmark''': 2C-T-2 was added to category B of the controlled substances list on August 23, 2003.<ref>{{cite web|url=https://www.riigiteataja.ee/aktilisa/1090/2201/1004/109022011004Lisa1.pdf|language=et|page=1|title=I Nimekiri}}</ref>{{Verify source|date=October 2020}} | ||
*'''Japan | *'''Germany''': 2C-T-2 is controlled under Anlage I BtMG (''Narcotics Act, Schedule I'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Gesetz über den Verkehr mit Betäubungsmitteln: Anlage I|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> as of October 10, 1998.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl198s3126a.pdf|title=Zwölfte Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften|publisher=Bundesanzeiger Verlag|work=Bundesgesetzblatt Jahrgang 1998 Teil I Nr. 68|page=3126|publication-date=October 9, 1998|language=de|oclc=231871244|issn=0341-1095|date=October 7, 1998}}</ref> It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/__29.html|title=Gesetz über den Verkehr mit Betäubungsmitteln: § 29|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> | ||
*'''Latvia | *'''Italy''': 2C-T-2 was added to the "Tabella 1" in a Jan 11, 2005 Ministry of Health statement.{{citation needed}} | ||
*'''Netherlands | *'''Japan''': 2C-T-2 is controlled as a "Designated Substance" (Shitei-Yakubutsu) by the Pharmaceutical Affairs Law, making it illegal to possess or sell.{{citation needed}} | ||
*'''Switzerland | *'''Latvia''': 2C-T-2 is a Schedule I controlled substance.<ref>{{cite web|url=http://likumi.lv/doc.php?id=121086|title=Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem|publisher=VSIA Latvijas Vēstnesis|access-date=January 1, 2020|publication-date=November 10, 2005|language=lv}}</ref> | ||
*''' | *'''The Netherlands''': 2C-T-2 was classified as an unregistered pharmaceutical as of April 12, 1999. Unlicensed manufacture, sale, import, trade and possession of this substance can be prosecuted.{{citation needed}} | ||
*''' | *'''Switzerland''': 2C-T-2 is a controlled substance specifically named under Verzeichnis D.<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-2 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-2 is a Schedule 1 drug in the U.S., making it illegal to possess, manufacture, or import.{{citation needed}} | |||
==See also== | ==See also== | ||
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==External links== | ==External links== | ||
*[ | *[https://en.wikipedia.org/wiki/2C-T-2 2C-T-2 (Wikipedia)] | ||
*[ | *[https://erowid.org/chemicals/2ct2/2ct2.shtml 2C-T-2 (Erowid Vault)] | ||
*[ | *[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=40 2C-T-2 (PiHKAL / Isomer Design)] | ||
===Discussion=== | |||
*[http://www.bluelight.org/vb/threads/95005-The-Big-amp-Dandy-2C-T-2-Thread 2C-T-2 (Bluelight)] | *[http://www.bluelight.org/vb/threads/95005-The-Big-amp-Dandy-2C-T-2-Thread 2C-T-2 (Bluelight)] | ||
==References== | ==References== | ||
<references/> | <references/> | ||
[[Category:Psychoactive substance]] | [[Category:Psychoactive substance]] | ||
[[Category:Psychedelic]] | |||
[[Category:2C-T-x]] | |||
[[Category:Research chemical]] | [[Category:Research chemical]] | ||
{{#set:Featured=true | {{#set:Featured=true | ||