2C-T-4
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| Clinical data | |
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| Other names | 4-Isopropylthio-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-isopropylthiophenethylamine |
| Routes of administration | Oral[1] |
| Drug class | Serotonin; 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen |
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| Pharmacokinetic data | |
| Duration of action | 12–18 hours[1] |
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| Chemical and physical data | |
| Formula | C13H21NO2S |
| Molar mass | 255.38 g·mol−1 |
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2C-T-4, also known as 4-isopropylthio-2,5-dimethoxyphenethylamine, is a psychedelic phenethylamine of the 2C family.[1][2] It was first synthesized by Alexander Shulgin and is used as entheogenic recreational drug.[1]
Effects
[edit]2C-T-4 produces psychedelic and entheogenic effects that develop slowly and can last 12 to 18 hours.[1] While users may experience virtually no effects for the first hour after ingestion, results vary drastically between individuals and range from hallucination and euphoria to intense sickness and anxiety.[1] Shulgin devoted a chapter in the first part of his book PiHKAL to this compound, describing an intense "plus-four" psychedelic experience mediated by a twelve milligram dose.
Interactions
[edit]Pharmacology
[edit]| 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: [3][4][5][6] | |
2C-T-4 acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A receptor.[5][4] The mechanism that produces 2C-T-4's hallucinogenic and entheogenic 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
[edit]2C-T-4 is the 2-carbon homolog of Aleph-4. The full chemical name is 2-[4-(isopropylthio)-2,5-dimethoxyphenyl]-ethanamine. The drug has structural and pharmacodynamic properties similar to 2C-T-7 and 2C-T-19.[citation needed]
Homologue
[edit]
2C-T-4 has a homologue, the structural isomer Ψ-2C-T-4 (2,6-dimethoxy-4-(i)-propylthiophenethylamine). This compound was tested by Alexander Shulgin at a dose of 12 mg.
At this dosage its duration was very short and it produced few effects, however based on the research into the better characterized compound Ψ-DOM, the potency of Ψ-2C-T-4 is likely to be around 1/3 that of 2C-T-4 itself, so a more effective dosage of Ψ-2C-T-4 might be in the region of 20–60 mg;[1] however high doses such as this might well be associated with toxic side effects, and so extreme caution would be advised.
Society and culture
[edit]Popularity
[edit]2C-T-4 is relatively unknown on the black market, but has been sold to a limited extent on the research chemical market.[citation needed]
Legal status
[edit]Canada
[edit]As of October 31, 2016, 2C-T-4 is a controlled substance (Schedule III) in Canada.[7]
China
[edit]As of October 2015 2C-T-4 is a controlled substance in China.[8]
Denmark
[edit]2C-T-4 is added to the list of Schedule B controlled substances.[9]
Sweden
[edit]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.[10]
United States
[edit]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.[11]
References
[edit]- ^ a b c d e f g Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
- ^ Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
- ^ "Kᵢ Database". PDSP. 9 May 2025. Retrieved 9 May 2025.
- ^ a b Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)" (PDF). Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099.
- ^ a b Luethi D, Trachsel D, Hoener MC, Liechti ME (May 2018). "Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs)". Neuropharmacology. 134 (Pt A): 141–148. doi:10.1016/j.neuropharm.2017.07.012. PMID 28720478.
- ^ Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1" (PDF). J Pharmacol Exp Ther. 357 (1): 134–144. doi:10.1124/jpet.115.229765. PMID 26791601.
- ^ "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". Canada Gazette. 4 May 2016.
- ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" [Notice on the issuance of the "Regulations on the Listing of Non-Medicinal Narcotic Drugs and Psychotropic Drugs"] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
- ^ "Bekendtgørelse om euforiserende stoffer" [Executive Order on Euphoriant Drugs]. Retsinformation (legal information) (in Danish).
- ^ Larsson M (14 June 2007). "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor" [Ordinance amending the Ordinance (1999:58) on the prohibition of certain goods hazardous to health] (PDF). Svensk författningssamling (Swedish Constitution) (in Swedish). Archived from the original (PDF) on September 29, 2013. Retrieved January 24, 2022.
- ^ Portman RJ. "Synthetic Drug Abuse Prevention Act of 2012". Govtrack. Retrieved 22 July 2012.