Chemistry:2C-T-4

From HandWiki

2C-T-4, also known as 4-isopropylthio-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.[1][2] It is taken orally.[1]

2C-T-4 was first described in the scientific literature by Alexander Shulgin and colleagues in 1991.[3] Shortly after this, Shulgin described 2C-T-17 in greater detail in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 2C-T-4's dose range as 8 to 20 mg orally and its duration as 12 to 18 hours.[1] Its onset is 30 minutes to 2 hours and peak effects occur after 3 hours.[1] The effects of 2C-T-4 have been described and include psychedelic visuals among others.[1] Shulgin devoted a chapter in the first part of PiHKAL to 2C-T-4, describing an intense "plus-four" experience on the Shulgin Rating Scale with a 12 mg dose.[1]

Interactions

2C drugs are metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.[4][5] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C drugs.[4][5][6] This may result in overdose and serious toxicity.[6][4]

Pharmacology

Pharmacodynamics

2C-T-4 activities
Target Affinity (Ki, nM)
5-HT1A 470–916
5-HT1B ND
5-HT1D ND
5-HT1E ND
5-HT1F ND
5-HT2A 27.9–54 (Ki)
5.5–220 (EC50)
56–87% (Emax)
5-HT2B ND (Ki)
63–160 (EC50)
68–75% (Emax)
5-HT2C 180–295 (Ki)
ND (EC50)
ND (Emax)
5-HT3 ND
5-HT4 ND
5-HT5A ND
5-HT6 ND
5-HT7 ND
α1A 11,000
α1B, α1D ND
α2A 130–217
α2B, α2C ND
β1–β3 ND
D1 20,000
D2 16,000
D3 19,000
D4, D5 ND
H1 >25,000
H2–H4 ND
M1–M5 ND
I1 ND
σ1, σ2 ND
TAAR1 2,337–4,500 (Ki) (mouse)
19–53 (Ki) (rat)
3,700 (EC50) (mouse)
83 (EC50) (rat)
>30,000 (EC50) (human)
51% (Emax) (mouse)
67% (Emax) (rat)
SERT >30,000 (Ki)
113,000 (IC50)
ND (EC50)
NET 17,000 (Ki)
134,000 (IC50)
ND (EC50)
DAT >30,000 (Ki)
294,000 (IC50)
ND (EC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [7][8][9][10]

2C-T-4 acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A receptor.[9][8] The mechanism that produces 2C-T-4's hallucinogenic effects has not been specifically established, however it is most likely to result from 5-HT2A receptor activation in the brain, a mechanism of action shared by all of the hallucinogenic tryptamines and phenethylamines for which the mechanism of action is known.

Chemistry

2C-T-4 is the 2-carbon homologue of Aleph-4.[1] The full chemical name is 2-[4-(isopropylthio)-2,5-dimethoxyphenyl]-ethanamine.[1] The drug has structural and pharmacodynamic properties similar to 2C-T-7 and 2C-T-19.[1] A notable analogue of 2C-T-4 is the Ψ-PEA compound Ψ-2C-T-4.[1]

Synthesis

The chemical synthesis of 2C-T-4 has been described.[1]

Analogues

Analogues of 2C-T-4 include 2C-T, 2C-T-2, 2C-T-7, and Aleph-4, among others.[1]

History

2C-T-4 was first described in the scientific literature by Alexander Shulgin and colleagues in a journal article in 1991.[3] Shortly thereafter, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1]

Society and culture

Canada

As of October 31, 2016, 2C-T-4 is a controlled substance (Schedule III) in Canada.[11]

China

As of October 2015 2C-T-4 is a controlled substance in China.[12]

Denmark

2C-T-4 is added to the list of Schedule B controlled substances.[13]

Sweden

Sveriges riksdags health ministry Statens folkhälsoinstitut classified 2C-T-4 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 Jul 15, 2007, in their regulation SFS 2007:600 listed as 2,5-dimetoxi-4-isopropyltiofenetylamin (2C-T-4), making it illegal to sell or possess.[14]

United States

As of July 9, 2012, 2C-T-4 is a Schedule I substance in the United States, under the Synthetic Drug Abuse Prevention Act of 2012.[15]

See also

References

  1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 1.12 1.13 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml. 
  2. ↑ The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley: Transform Press. 2011. ISBN 978-0-9630096-3-0. https://books.google.com/books?id=68-huAAACAAJ. 
  3. ↑ 3.0 3.1 "Letters to the Editor [Re: Stolaroff (1990) - Central Nervous System (CNS) Activity of Two New Psychoactive Compounds"]. Journal of Psychoactive Drugs 23 (1): 95–96. January 1991. doi:10.1080/02791072.1991.10472583. ISSN 0279-1072. PMID 1941371. https://bibliography.maps.org/resources/download/11956. 
  4. ↑ 4.0 4.1 4.2 "2C or not 2C: phenethylamine designer drug review". J Med Toxicol 9 (2): 172–178. June 2013. doi:10.1007/s13181-013-0295-x. PMID 23494844. 
  5. ↑ 5.0 5.1 "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)". Biochem Pharmacol 73 (2): 287–297. January 2007. doi:10.1016/j.bcp.2006.09.022. PMID 17067556. 
  6. ↑ 6.0 6.1 "Drug-drug interactions involving classic psychedelics: A systematic review". J Psychopharmacol 38 (1): 3–18. January 2024. doi:10.1177/02698811231211219. PMID 37982394. 
  7. ↑ "Kᵢ Database". 9 May 2025. 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=12948&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D=&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=14677&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D=. 
  8. ↑ 8.0 8.1 "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)". Neuropharmacology 99: 546–553. December 2015. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099. 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. 
  9. ↑ 9.0 9.1 "Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs)". Neuropharmacology 134 (Pt A): 141–148. May 2018. doi:10.1016/j.neuropharm.2017.07.012. PMID 28720478. https://bitnest.netfirms.com/external/10.1016/j.neuropharm.2017.07.012. 
  10. ↑ "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". J Pharmacol Exp Ther 357 (1): 134–144. April 2016. doi:10.1124/jpet.115.229765. PMID 26791601. 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. 
  11. ↑ "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". Canada Gazette. 4 May 2016. http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php. 
  12. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in zh). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html. 
  13. ↑ "Bekendtgørelse om euforiserende stoffer" (in Danish). Retsinformation (legal information). https://www.retsinformation.dk/Forms/R0710.aspx?id=137169. 
  14. ↑ "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor" (in Swedish). Svensk författningssamling (Swedish Constitution). 14 June 2007. http://www.notisum.se/rnp/sls/sfs/20070600.pdf. 
  15. ↑ "Synthetic Drug Abuse Prevention Act of 2012". Govtrack. http://www.govtrack.us/congress/bills/112/s3190/text. 

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