2C-T-2: Difference between revisions

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| {{Abbrlink|MAO-B|Monoamine oxidase B}} || {{Abbr|ND|No data}} ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})
| {{Abbrlink|MAO-B|Monoamine oxidase B}} || {{Abbr|ND|No data}} ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})
|- class="sortbottom"
|- class="sortbottom"
| colspan="2" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Notes:''' The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. '''Refs:''' <ref name="PDSPKiDatabase">{{cite web | title=Kᵢ Database | website=PDSP | date=16 March 2025 | url=https://pdsp.unc.edu/kidb2/kidb/web/kis-results/index?KisResultsSearch%5Binput_receptors%5D=&KisResultsSearch%5Binput_sources%5D=&KisResultsSearch%5Binput_species%5D=&KisResultsSearch%5Binput_hot_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=12944&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D= | access-date=16 March 2025}}</ref><ref name="Ray2010">{{cite journal | vauthors = Ray TS | title = Psychedelics and the human receptorome | journal = PLOS ONE | volume = 5 | issue = 2 | pages = e9019 | date = February 2010 | pmid = 20126400 | pmc = 2814854 | doi = 10.1371/journal.pone.0009019 | doi-access = free | bibcode = 2010PLoSO...5.9019R | url = }}</ref><ref name="RickliLuethiReinisch2015">{{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 | issue = | pages = 546–553 | date = December 2015 | pmid = 26318099 | doi = 10.1016/j.neuropharm.2015.08.034 | url = https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf}}</ref><ref name="EshlemanForsterWolfrum2014">{{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 (Berl) | volume = 231 | issue = 5 | pages = 875–888 | date = March 2014 | pmid = 24142203 | pmc = 3945162 | doi = 10.1007/s00213-013-3303-6 | url = https://www.researchgate.net/profile/Michael-Forster-2/publication/258061356_Behavioral_and_neurochemical_pharmacology_of_six_psychoactive_substituted_phenethylamines_Mouse_locomotion_rat_drug_discrimination_and_in_vitro_receptor_and_transporter_binding_and_function/links/53d119a00cf2f7e53cfbcd68/Behavioral-and-neurochemical-pharmacology-of-six-psychoactive-substituted-phenethylamines-Mouse-locomotion-rat-drug-discrimination-and-in-vitro-receptor-and-transporter-binding-and-function.pdf}}</ref><ref name="PottieCannaertStove2020">{{cite journal | vauthors = Pottie E, Cannaert A, Stove CP | title = In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor | journal = Arch Toxicol | volume = 94 | issue = 10 | pages = 3449–3460 | date = October 2020 | pmid = 32627074 | doi = 10.1007/s00204-020-02836-w | bibcode = 2020ArTox..94.3449P | url = | hdl = 1854/LU-8687071 | hdl-access = free }}</ref><ref name="WagmannBrandtStratford2019">{{cite journal | vauthors = Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR | title = Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases | journal = Drug Test Anal | volume = 11 | issue = 2 | pages = 318–324 | date = February 2019 | pmid = 30188017 | doi = 10.1002/dta.2494 | url = }}</ref><ref name="SimmlerBuchyChaboz2016">{{cite journal | vauthors = Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME | title = In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1 | journal = J Pharmacol Exp Ther | volume = 357 | issue = 1 | pages = 134–144 | date = April 2016 | pmid = 26791601 | doi = 10.1124/jpet.115.229765 | url = https://web.archive.org/web/20250509235235/https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA}}</ref>
| colspan="2" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Notes:''' The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. '''Refs:''' <ref name="PDSPKiDatabase">{{cite web | title=Kᵢ Database | website=PDSP | date=16 March 2025 | url=https://pdsp.unc.edu/kidb2/kidb/web/kis-results/index?KisResultsSearch%5Binput_receptors%5D=&KisResultsSearch%5Binput_sources%5D=&KisResultsSearch%5Binput_species%5D=&KisResultsSearch%5Binput_hot_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=12944&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D= | access-date=16 March 2025}}</ref><ref name="Ray2010">{{cite journal | vauthors = Ray TS | title = Psychedelics and the human receptorome | journal = PLOS ONE | volume = 5 | issue = 2 | pages = e9019 | date = February 2010 | pmid = 20126400 | pmc = 2814854 | doi = 10.1371/journal.pone.0009019 | doi-access = free | bibcode = 2010PLoSO...5.9019R | url = }}</ref><ref name="RickliLuethiReinisch2015">{{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 | issue = | pages = 546–553 | date = December 2015 | pmid = 26318099 | doi = 10.1016/j.neuropharm.2015.08.034 | url = https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf}}</ref><ref name="EshlemanForsterWolfrum2014">{{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 (Berl) | volume = 231 | issue = 5 | pages = 875–888 | date = March 2014 | pmid = 24142203 | pmc = 3945162 | doi = 10.1007/s00213-013-3303-6 | url = https://www.researchgate.net/publication/258061356}}</ref><ref name="PottieCannaertStove2020">{{cite journal | vauthors = Pottie E, Cannaert A, Stove CP | title = In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor | journal = Arch Toxicol | volume = 94 | issue = 10 | pages = 3449–3460 | date = October 2020 | pmid = 32627074 | doi = 10.1007/s00204-020-02836-w | bibcode = 2020ArTox..94.3449P | url = | hdl = 1854/LU-8687071 | hdl-access = free }}</ref><ref name="WagmannBrandtStratford2019">{{cite journal | vauthors = Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR | title = Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases | journal = Drug Test Anal | volume = 11 | issue = 2 | pages = 318–324 | date = February 2019 | pmid = 30188017 | doi = 10.1002/dta.2494 | url = }}</ref><ref name="SimmlerBuchyChaboz2016">{{cite journal | vauthors = Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME | title = In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1 | journal = J Pharmacol Exp Ther | volume = 357 | issue = 1 | pages = 134–144 | date = April 2016 | pmid = 26791601 | doi = 10.1124/jpet.115.229765 | url = https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA| archive-url = https://web.archive.org/web/20250509235235/https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA | archive-date = 9 May 2025 }}</ref>
|}
|}


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===China===
===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=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 }}</ref>
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=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 }}</ref>
===Finland===
2C-T-2 is classified as a narcotic drug in Finland.<ref>{{cite web | url=http://www.finlex.fi/fi/laki/ajantasa/2008/20080543 | title=Valtioneuvoston asetus huumausaineina pidettävistä aineista, valmisteista ja kasveista &#124; 543/2008 &#124; Lainsäädäntö &#124; Finlex }}</ref>


===Netherlands===
===Netherlands===

Latest revision as of 16:28, 16 June 2025

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| _other_data=2-[4-(ethylsulfanyl)-2,5-dimethoxyphenyl]ethan-1-amine

| _image_0_or_2 = 2C-T-2 2DACS.svg2C-T-2 anim.gif | _image_LR =

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2C-T-2, also known as 4-ethylthio-2,5-dimethoxyphenethylamine, is a psychedelic and entactogenic phenethylamine of the 2C family.[2] 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.[3][1] 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.[1]

Pharmacology

2C-T-2 activities
Target Affinity (Ki, nM)
5-HT1A 370–1,740 (Ki)
3,000 (Template:Abbrlink)
76% (Template:Abbrlink)
5-HT1B 858
5-HT1D 86
5-HT1E 415
5-HT1F ND
5-HT2A 9–40 (Ki)
0.354–80 (EC50)
67–107% (Emax)
5-HT2B 6–69 (Ki)
130 (EC50)
75% (Emax)
5-HT2C 14–54 (Ki)
0.0233–3.8 (EC50)
87–107% (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A >10,000
5-HT6 1,362
5-HT7 969
α1A 17,000
α1B >10,000
α1D ND
α2A 230–730
α2B 982
α2C 166
β1 9,202
β2 1,184
β3 ND
D1 15,000
D2 2,795–5,100
D3 1,835–11,000
D4 >10,000
D5 >10,000
H1–H4 >10,000
M1 >10,000
M2 >10,000
M3 692
M4 >10,000
M5 1,502
I1 2,080
σ1 3,870
σ2 >10,000
Template:Abbrlink 2,200 (Ki) (mouse)
40 (Ki) (rat)
96 (EC50) (mouse)
4,300 (EC50) (rat)
>10,000 (EC50) (human)
54% (Emax) (mouse)
86% (Emax) (rat)
Template:Abbrlink 13,000 (Ki)
62,000 (Template:Abbrlink)
IA (EC50)
Template:Abbrlink >30,000 (Ki)
153,000 (IC50)
IA (EC50)
Template:Abbrlink >30,000 (Ki)
332,000 (IC50)
IA (EC50)
Template:Abbrlink ND (IC50)
Template:Abbrlink ND (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [4][5][6][7][8][9][10]

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,[11] a mechanism of action shared by the hallucinogenic tryptamines and phenethylamines to varying degrees.[12][13] 2C-T-2 has also shown to be a partial agonist of adrenergic receptors.[14]

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.[15]

Severe 'intoxication' on 2C series drugs has been observed as behavior that includes: intense hallucinations, agitation, aggression, violence, dysphoria, hypertension, tachycardia, seizures, and hyperthermia.[16]

Interactions

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2C-T-2 is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.[17][18] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-T-2.[17][18][19] This may result in overdose and serious toxicity.[19][17]

Legal status

Argentina

2C-T-2 is also a controlled substance in Argentina as well as 2C-B and 2C-I.[20]

Canada

As of October 31, 2016, 2C-T-2 is a controlled substance (Schedule III) in Canada.[21]

China

As of October 2015 2C-T-2 is a controlled substance in China.[22]

Finland

2C-T-2 is classified as a narcotic drug in Finland.[23]

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[24] 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.[25]

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.[26]

Australia

2C-T-2 is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[27] 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.[27]

See also

References

Template:Reflist

External links

Template:Psychedelics Template:Serotonin receptor modulators Template:TAAR modulators Script error: No such module "Navbox".

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  18. ↑ a b Script error: No such module "Citation/CS1".
  19. ↑ a b Script error: No such module "Citation/CS1".
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  21. ↑ Script error: No such module "citation/CS1".
  22. ↑ Script error: No such module "citation/CS1".
  23. ↑ Script error: No such module "citation/CS1".
  24. ↑ Script error: No such module "citation/CS1".
  25. ↑ Script error: No such module "citation/CS1".
  26. ↑ Script error: No such module "citation/CS1".
  27. ↑ a b Script error: No such module "citation/CS1".
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