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2C-T-4
| Field | Value | ||||
|---|---|---|---|---|---|
| Verifiedfields | changed | ||||
| Watchedfields | changed | ||||
| verifiedrevid | 477216693 | ||||
| image | 2C-T-4 2DACS.svg | ||||
| image_class | skin-invert-image | ||||
| width | 200px | ||||
| image2 | 2C-T-4-3d-sticks.png | ||||
| image_class2 | bg-transparent | ||||
| width2 | 200px | ||||
| routes_of_administration | Oral | ||||
| class | Serotonin; [5-HT2 receptor](5-ht2-receptor) agonist; Serotonergic psychedelic; Hallucinogen | ||||
| ATC_prefix | None | ||||
| onset | 30 minutes–2 hours | ||||
| Peak: 3 hours | |||||
| duration_of_action | 12–18 hours | ||||
| CAS_number_Ref | |||||
| CAS_number | 207740-25-8 | ||||
| PubChem | 44350070 | ||||
| ChemSpiderID_Ref | |||||
| ChemSpiderID | 21106232 | ||||
| UNII_Ref | |||||
| UNII | 558WSD71D4 | ||||
| KEGG_Ref | |||||
| KEGG | C22735 | ||||
| ChEMBL_Ref | |||||
| ChEMBL | 338259 | ||||
| synonyms | 4-Isopropylthio-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-isopropylthiophenethylamine | ||||
| IUPAC_name | 2-{2,5-Dimethoxy-4-[(propan-2-yl)sulfanyl]phenyl}ethan-1-amine | ||||
| C | 13 | H=21 | N=1 | O=2 | S=1 |
| SMILES | CC(C)Sc1cc(OC)c(cc1OC)CCN | ||||
| StdInChI_Ref | |||||
| StdInChI | 1S/C13H21NO2S/c1-9(2)17-13-8-11(15-3)10(5-6-14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3 | ||||
| StdInChIKey_Ref | |||||
| StdInChIKey | HDYZSVKZKDPLDT-UHFFFAOYSA-N |
| Drugs.com =
Peak: 3 hours | elimination_half-life =
2C-T-4, also known as 4-isopropylthio-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families. It is taken orally.
2C-T-4 was first described in the scientific literature by Alexander Shulgin and colleagues in 1991. Shortly after this, Shulgin described 2C-T-17 in greater detail in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).
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 20mg orally and its duration as 12 to 18hours. Its onset is 30minutes to 2hours and peak effects occur after 3hours. The effects of 2C-T-4 have been described and include psychedelic visuals among others. 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 12mg dose.
Interactions
2C drugs are metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B. Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C drugs. This may result in overdose and serious toxicity.
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| [5-HT1A](5-ht1a-receptor) | 470–916 |
| [5-HT1B](5-ht1b-receptor) | ND |
| [5-HT1D](5-ht1d-receptor) | ND |
| [5-HT1E](5-ht1e-receptor) | ND |
| [5-HT1F](5-ht1f-receptor) | ND |
| [5-HT2A](5-ht2a-receptor) | 27.9–54 (Ki) |
| 5.5–220 () | |
| 56–87% () | |
| [5-HT2B](5-ht2b-receptor) | ND (Ki) |
| 63–160 (EC50) | |
| 68–75% (Emax) | |
| [5-HT2C](5-ht2c-receptor) | 180–295 (Ki) |
| ND (EC50) | |
| ND (Emax) | |
| [5-HT3](5-ht3-receptor) | ND |
| [5-HT4](5-ht4-receptor) | ND |
| [5-HT5A](5-ht5a-receptor) | ND |
| [5-HT6](5-ht6-receptor) | ND |
| [5-HT7](5-ht7-receptor) | 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 |
| 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) | |
| 30,000 (Ki) | |
| 113,000 () | |
| ND (EC50) | |
| 17,000 (Ki) | |
| 134,000 (IC50) | |
| ND (EC50) | |
| 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:** |
2C-T-4 acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A receptor. 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. 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. A notable analogue of 2C-T-4 is the Ψ-PEA compound Ψ-2C-T-4.
Synthesis
The chemical synthesis of 2C-T-4 has been described.
Analogues
Analogues of 2C-T-4 include 2C-T, 2C-T-2, 2C-T-7, and Aleph-4, among others.
History
2C-T-4 was first described in the scientific literature by Alexander Shulgin and colleagues in a journal article in 1991. Shortly thereafter, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).
Society and culture
Legal status
Canada
As of October 31, 2016, 2C-T-4 is a controlled substance (Schedule III) in Canada.
China
As of October 2015 2C-T-4 is a controlled substance in China.
Denmark
2C-T-4 is added to the list of Schedule B controlled substances.
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.
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.
References
References
- {{CitePiHKAL
- (2011). "The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds". Transform Press.
- (June 2013). "2C or not 2C: phenethylamine designer drug review". J Med Toxicol.
- (January 2007). "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)". Biochem Pharmacol.
- (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". J Psychopharmacol.
- (9 May 2025). "Kᵢ Database".
- (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)". Neuropharmacology.
- (May 2018). "Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs)". Neuropharmacology.
- (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". J Pharmacol Exp Ther.
- (January 1991). "Letters to the Editor [Re: Stolaroff (1990) - Central Nervous System (CNS) Activity of Two New Psychoactive Compounds]". Journal of Psychoactive Drugs.
- (4 May 2016). "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". Canada Gazette.
- (27 September 2015). "关于印发《非药用类麻醉药品和精神药品列管办法》的通知". China Food and Drug Administration.
- "Bekendtgørelse om euforiserende stoffer". Retsinformation (legal information).
- (14 June 2007). "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor". Svensk författningssamling (Swedish Constitution).
- "Synthetic Drug Abuse Prevention Act of 2012". Govtrack.
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