2C-T-2
{{Infobox drug
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| Watchedfields = verified
| verifiedrevid = 477216630
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| image = 2C-T-2 2DACS.svg
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| image2 = 2C-T-2 anim.gif
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| routes_of_administration = Oral
| class = Serotonin; 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
| ATC_prefix = None
| ATC_suffix =
| legal_AU = S9
| legal_BR = F2
| legal_CA = Schedule III
| legal_DE =
| legal_US = Schedule I
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| duration_of_action = 6–8 hours
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| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 207740-24-7
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| PubChem = 12074193
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16787961
| UNII = WPS2KSX2TJ
| KEGG = C22715
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| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 339223
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| synonyms = 4-Ethylthio-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-ethylthiophenethylamine
| IUPAC_name = 2-[4-(ethylsulfanyl)-2,5-dimethoxyphenyl]ethan-1-amine
| C=12 | H=19 | N=1 | O=2 | S=1
| SMILES = CCSc1cc(OC)c(cc1OC)CCN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H19NO2S/c1-4-16-12-8-10(14-2)9(5-6-13)7-11(12)15-3/h7-8H,4-6,13H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HCWQGDLBIKOJPM-UHFFFAOYSA-N
}}
2C-T-2, also known as 4-ethylthio-2,5-dimethoxyphenethylamine, is a psychedelic and entactogenic phenethylamine of the 2C family.{{Cite web |date=2001-02-06 |title=Stolaroff's & Well's Study |url=https://erowid.org/chemicals/2ct7/article1/stolaroff.shtml |access-date=2023-10-30 |website=erowid.org}} It was first synthesized in 1981 by Alexander Shulgin, and rated by him as one of the "magical half-dozen" most important psychedelic phenethylamine compounds.{{cite journal | vauthors = Theobald DS, Staack RF, Puetz M, Maurer HH | title = New designer drug 2,5-dimethoxy-4-ethylthio-beta-phenethylamine (2C-T-2): studies on its metabolism and toxicological detection in rat urine using gas chromatography/mass spectrometry | journal = Journal of Mass Spectrometry | volume = 40 | issue = 9 | pages = 1157–1172 | date = September 2005 | pmid = 16041763 | doi = 10.1002/jms.890 | bibcode = 2005JMSp...40.1157T }}{{cite web|url=http://www.erowid.org/library/books_online/pihkal/pihkal040.shtml|work = Erowid Online Books : "PIHKAL" | title = #40 2C-T-2 }} The drug has structural and pharmacodynamic properties similar to those of 2C-T-7 ("Blue Mystic").
Dosage
In Alexander Shulgin's book PiHKAL, the dosage range is listed as 12 to 25 mg.
Pharmacology
The mechanism of action that produces 2C-T-2’s hallucinogenic and entheogenic effects is shown to be most likely a result from action as a 5-HT2A, 5-HT2B, and 5-HT2C serotonin receptor agonist,{{cite journal | vauthors = Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME | title = Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs) | journal = Neuropharmacology | volume = 99 | pages = 546–553 | date = December 2015 | pmid = 26318099 | doi = 10.1016/j.neuropharm.2015.08.034 | s2cid = 10382311 | url = http://edoc.unibas.ch/56163/1/20170921163006_59c3cceeb8e5d.pdf }} a mechanism of action shared by the hallucinogenic tryptamines and phenethylamines to varying degrees.{{cite journal | vauthors = Eshleman AJ, Forster MJ, Wolfrum KM, Johnson RA, Janowsky A, Gatch MB | title = Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function | journal = Psychopharmacology | volume = 231 | issue = 5 | pages = 875–888 | date = March 2014 | pmid = 24142203 | pmc = 3945162 | doi = 10.1007/s00213-013-3303-6 }}{{cite journal | vauthors = Rickli A, Moning OD, Hoener MC, Liechti ME | title = Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens | journal = European Neuropsychopharmacology | volume = 26 | issue = 8 | pages = 1327–1337 | date = August 2016 | pmid = 27216487 | doi = 10.1016/j.euroneuro.2016.05.001 | s2cid = 6685927 | url = http://edoc.unibas.ch/53326/1/20170117174852_587e4af45b658.pdf }} 2C-T-2 has also shown to be a partial agonist of adrenergic receptors.{{cite journal | vauthors = Luethi D, Trachsel D, Hoener MC, Liechti ME | title = Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs) | journal = Neuropharmacology | volume = 134 | issue = Pt A | pages = 141–148 | date = May 2018 | pmid = 28720478 | doi = 10.1016/j.neuropharm.2017.07.012 | series = Designer Drugs and Legal Highs | s2cid = 7135811 | url = https://edoc.unibas.ch/57358/1/20170920150712_59c2680084ec5.pdf }}
Dangers
A potential risk of neurotoxicity from 2C-T-2 use (and 2C chemical series in general) has been shown in serotonergic and dopaminergic containing neurons. This has also been shown to be magnified in serotonergic-containing cells with combined use of 2C series drugs with alcohol, MDMA, and methamphetamine.{{Cite journal | vauthors = Asanuma M, Miyazaki I, Funada M |date= July 2020 |title=The neurotoxicity of psychoactive phenethylamines "2C series" in cultured monoaminergic neuronal cell lines |url=https://doi.org/10.1007/s11419-020-00527-w |journal=Forensic Toxicology |language=en |volume=38 |issue=2 |pages=394–408 |doi=10.1007/s11419-020-00527-w |s2cid= 211218167 |issn=1860-8973|url-access=subscription }}
Severe 'intoxication' on 2C series drugs has been observed as behavior that includes: intense hallucinations, agitation, aggression, violence, dysphoria, hypertension, tachycardia, seizures, and hyperthermia.{{cite journal | vauthors = Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM | title = 2C or not 2C: phenethylamine designer drug review | journal = Journal of Medical Toxicology | volume = 9 | issue = 2 | pages = 172–178 | date = June 2013 | pmid = 23494844 | pmc = 3657019 | doi = 10.1007/s13181-013-0295-x }}
Interactions
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
2C-T-2 is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.{{cite journal | vauthors = Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM | title = 2C or not 2C: phenethylamine designer drug review | journal = J Med Toxicol | volume = 9 | issue = 2 | pages = 172–178 | date = June 2013 | pmid = 23494844 | pmc = 3657019 | doi = 10.1007/s13181-013-0295-x | url = }}{{cite journal | vauthors = Theobald DS, Maurer HH | title = Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series) | journal = Biochem Pharmacol | volume = 73 | issue = 2 | pages = 287–297 | date = January 2007 | pmid = 17067556 | doi = 10.1016/j.bcp.2006.09.022 | url = }} Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-T-2.{{Cite journal |vauthors=Halman A, Kong G, Sarris J, Perkins D |date=January 2024 |title=Drug-drug interactions involving classic psychedelics: A systematic review |journal=J Psychopharmacol |volume=38 |issue=1 |pages=3–18 |doi=10.1177/02698811231211219 |pmc=10851641 |pmid=37982394}} This may result in overdose and serious toxicity.
Legal status
=Argentina=
2C-T-2 is also a controlled substance in Argentina as well as 2C-B and 2C-I.{{cite web | url = http://www.mpf.gov.ar/biblioteca/newsletter/n197/DECRETO_299_2010.pdf | archive-url = https://web.archive.org/web/20110706084437/http://www.mpf.gov.ar/biblioteca/newsletter/n197/DECRETO_299_2010.pdf | archive-date = 6 July 2011 | title = DECRETO 299/2010 - PODER EJECUTIVO NACIONAL (P.E.N.) Estupefacientes - Actualización de la lista y demás sustancias químicas que deberán ser incluidas en los alcances de la ley 23.737 - Sustitución del anexo I del dec. 722/91. Publicado en: BOLETIN OFICIAL 04/03/2010 | trans-title = DECREE 299/2010 - NATIONAL EXECUTIVE POWER (P.E.N.) Narcotics - Updating of the list and other chemical substances that must be included in the scope of Law 23,737 - Substitution of annex I of dec. 722/91 | language = Spanish | date = 3 February 2010 }}
=Canada=
As of October 31, 2016, 2C-T-2 is a controlled substance (Schedule III) in Canada.{{cite web|url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php|title=Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)| publisher = Government of Canada, Public Works and Government Services Canada, Public Services and Procurement Canada, Integrated Services Branch, Canada |date=4 May 2016}}
=China=
As of October 2015 2C-T-2 is a controlled substance in China.{{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=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}
=Netherlands=
The Netherlands became the first country in the world to ban 2C-T-2, and classify it as a hard drug, by law. In April, 1999, 2C-T-2 became a list I drug of the Opium Law.
=Sweden=
Schedule I in Sweden.
2C-T-2 was first classified as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of April 1, 1999, under SFS 1999:58{{cite web|url=http://www.notisum.se/rnp/sls/fakta/a9990058.HTM|title=Förordning (1999:58) om förbud mot vissa hälsofarliga varor|website=www.notisum.se|access-date=2013-09-15|archive-date=2013-10-04|archive-url=https://web.archive.org/web/20131004215233/http://www.notisum.se/rnp/sls/fakta/a9990058.HTM|url-status=dead}} that made it illegal to sell or possess.
The Riksdag added 2C-T-2 to Narcotic Drugs Punishments Act under Swedish schedule I ("substances, plant materials and fungi which normally do not have medical use") as of March 16, 2004, published by Medical Products Agency (MPA) in regulation LVFS 2004:3 listed as 2C-T-2, 2,5-dimetoxi-4-etyltiofenetylamin.{{cite web | url = https://lakemedelsverket.se/upload/lvfs/LVFS_2004-3.pdf | title = Läkemedelsverkets författningssamling | publisher = lakemedelsverket.se | language = sv}}
=United Kingdom=
2C-T-2 and all other compounds featured in PiHKAL are illegal drugs in the United Kingdom.
=United States=
2C-T-2 is specifically listed as a schedule I substance under SEC. 1152 of S.3187: Food and Drug Administration Safety and Innovation Act of 2012.{{Cite web |title=21 U.S. Code § 812 - Schedules of controlled substances |url=https://www.law.cornell.edu/uscode/text/21/812|access-date=2022-12-22 |website=Cornell University |language=en}}
=Australia=
2C-T-2 is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).{{cite web | title = Poisons Standard October 2015 | url = https://www.comlaw.gov.au/Details/F2015L01534 | date = October 2015 | work = Federal Register of Legislation | publisher = Australian Government, Department of Health, Therapeutic Goods Administration }} A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.
See also
References
{{reflist}}
External links
- [https://isomerdesign.com/pihkal/explore/40 2C-T-2 - Isomer Design]
- [https://psychonautwiki.org/wiki/2C-T-2 2C-T-2 - PsychonautWiki]
- [http://www.erowid.org/chemicals/2ct2/2ct2.shtml 2C-T-2 vault - Erowid]
- [https://erowid.org/library/books_online/pihkal/pihkal040.shtml 2C-T-2 - PiHKAL - Erowid]
- [https://isomerdesign.com/pihkal/read/pk/40 2C-T-2 - PiHKAL - Isomer Design]
- [https://tripsitter.com/2ct2/ 2C-T-2: Potential Therapeutic Alternative to MDMA?]
- [http://www.erowid.org/chemicals/2ct7/article1/article1.shtml Sulfurous Samadhi: An Investigation of 2C-T-2 & 2C-T-7 - Erowid]
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{TAAR modulators}}
{{Phenethylamines}}
Category:Psychedelic phenethylamines