2C-T-2: Difference between revisions
>David Hedlund {{DangerousInteractions/2C-T-x}} |
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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. | 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>Shulgin | 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 generally characterize 2C-T-2 as a highly dose sensitive psychedelic known for its open headspace and unpredictable [[body load]]. | 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 | 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. | ||
==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>Stolaroff | 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 (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> | 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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===Dependence and abuse potential=== | ===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. | 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 | 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: | ||
{ | {| | ||
|- | |||
| | |||
*'''[[5-MeO-MiPT]]''' | |||
*'''[[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]]''' | |||
|} | |||
==Legal status== | ==Legal status== | ||
*'''Australia | 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> | ||
*'''Austria | |||
*'''Belgium | *'''Australia''': 2C-T-2 is illegal in Australia as of 2005.{{citation needed}} | ||
*'''Brazil | *'''Austria''': 2C-T-2 is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).{{citation needed}} | ||
*'''Canada | *'''Belgium''': 2C-T-2 was added to the list of illegal psychotropic substances on Nov 8, 2004.{{citation needed}} | ||
*'''China | *'''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> | ||
*'''Denmark | *'''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> | ||
*'''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}} | |||
*'''Italy | *'''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> | ||
*'''Japan | *'''Italy''': 2C-T-2 was added to the "Tabella 1" in a Jan 11, 2005 Ministry of Health statement.{{citation needed}} | ||
*'''Latvia | *'''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}} | ||
*'''Netherlands | *'''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> | ||
*'''Switzerland | *'''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}} | ||
*'''United Kingdom | *'''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 States | *'''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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==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 |