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2C-T-2


FieldValue
Verifiedfieldsverified
Watchedfieldsverified
verifiedrevid477216630
image2C-T-2 2DACS.svg
image_classskin-invert-image
width225px
image22C-T-2 3D.png
image_class2bg-transparent
width2200px
routes_of_administrationOral
classSerotonin; [5-HT2 receptor](5-ht2-receptor) agonist; Serotonergic psychedelic; Hallucinogen
ATC_prefixNone
legal_AUS9
legal_BRF2
legal_CASchedule III
legal_USSchedule I
onset≤1 hour
duration_of_action6–8 hours
CAS_number_Ref
CAS_number207740-24-7
PubChem12074193
ChemSpiderID_Ref
ChemSpiderID16787961
UNIIWPS2KSX2TJ
KEGGC22715
ChEMBL_Ref
ChEMBL339223
synonyms4-Ethylthio-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-ethylthiophenethylamine
IUPAC_name2-[4-(ethylsulfanyl)-2,5-dimethoxyphenyl]ethan-1-amine
C12H=19N=1O=2S=1
SMILESCCSc1cc(OC)c(cc1OC)CCN
StdInChI_Ref
StdInChI1S/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
StdInChIKeyHCWQGDLBIKOJPM-UHFFFAOYSA-N

| Drugs.com =

| elimination_half-life =

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

The drug acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A receptor.

2C-T-2 was discovered by Alexander Shulgin in 1981 and was first described in the scientific literature by Myron Stolaroff in 1990.

Use and effects

In Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known and Loved), the dose range is listed as 12 to 25mg orally and its duration as 6 to 8hours. Its onset is within 1hour and peak effects occur after 1 to 2hours. The effects of 2C-T-2 have been described. Shulgin rated it as one of the "magical half-dozen" most important psychedelic phenethylamines, along with mescaline, 2C-B, 2C-T-7, and others.

Toxicity

A potential risk of neurotoxicity from 2C-T-2 use (and 2C chemical series in general) has been shown in serotonergic and dopaminergic neurons, however the assay used concentrations unlikely to translate to recreational use of the compound (50 μM). This has also been shown to be magnified in serotonergic-containing cells with combined use of 2C series drugs with alcohol, MDMA, and methamphetamine.

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

Interactions

2C-T-2 is 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-T-2. This may result in overdose and serious toxicity.

Pharmacology

Pharmacodynamics

TargetAffinity (Ki, nM)
[5-HT1A](5-ht1a-receptor)370–1,740 (Ki)
3,000 ()
76% ()
[5-HT1B](5-ht1b-receptor)858
[5-HT1D](5-ht1d-receptor)86
[5-HT1E](5-ht1e-receptor)415
[5-HT1F](5-ht1f-receptor)ND
[5-HT2A](5-ht2a-receptor)9–40 (Ki)
0.354–80 (EC50)
67–107% (Emax)
[5-HT2B](5-ht2b-receptor)6–69 (Ki)
130 (EC50)
75% (Emax)
[5-HT2C](5-ht2c-receptor)14–54 (Ki)
0.0233–3.8 (EC50)
87–107% (Emax)
[5-HT3](5-ht3-receptor)10,000
[5-HT4](5-ht4-receptor)ND
[5-HT5A](5-ht5a-receptor)10,000
[5-HT6](5-ht6-receptor)1,362
[5-HT7](5-ht7-receptor)969
α1A17,000
α1B10,000
α1DND
α2A230–730
α2B982
α2C166
β19,202
β21,184
β3ND
D115,000
D22,795–5,100
D31,835–11,000
D410,000
D510,000
H1–H410,000
M110,000
M210,000
M3692
M410,000
M51,502
I12,080
σ13,870
σ210,000
2,200 (Ki) (mouse)
40 (Ki) (rat)
96 (EC50) (mouse)
4,300 (EC50) (rat)
10,000 (EC50) (human)
54% (Emax) (mouse)
86% (Emax) (rat)
13,000 (Ki)
62,000 ()
IA (EC50)
30,000 (Ki)
153,000 (IC50)
IA (EC50)
30,000 (Ki)
332,000 (IC50)
IA (EC50)
ND (IC50)
ND (IC50)
**Notes:** The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. **Refs:**

2C-T-2 acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A and 5-HT2C receptors. The mechanism of action that produces 2C-T-2's hallucinogenic effects is shown to be most likely a result from action as a serotonin 5-HT2A, 5-HT2B, and 5-HT2C serotonin receptor agonist, a mechanism of action shared by the psychedelic tryptamines and phenethylamines to varying degrees. 2C-T-2 has also shown to be a partial agonist of adrenergic receptors.

Chemistry

Synthesis

The chemical synthesis of 2C-T-2 has been described.

Analogues

Analogues of 2C-T-2 include 2C-T (2C-T-1), 2C-T-4, 2C-T-7, Aleph-2, and 25T2-NBOMe, among others.

History

2C-T-2 was first synthesized by Alexander Shulgin in 1981. He discovered its psychedelic effects that same year. The drug was first described in the scientific literature by Myron Stolaroff in 1990. Subsequently, it was described in greater detail in a 1991 publication by Shulgin and colleagues and in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). Following this, 2C-T-2 emerged as a novel designer drug in the 1990s.

Society and culture

Argentina

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

Australia

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

Canada

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

China

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

Finland

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

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 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.

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.

References

References

  1. {{CitePiHKAL http://www.erowid.org/library/books_online/pihkal/pihkal040.shtml
  2. (6 February 2001). "Sulfurous Samadhi: Stolaroff's & Well's Study".
  3. (July 2020). "The neurotoxicity of psychoactive phenethylamines "2C series" in cultured monoaminergic neuronal cell lines". Forensic Toxicology.
  4. (June 2013). "2C or not 2C: phenethylamine designer drug review". Journal of Medical Toxicology.
  5. (January 2007). "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)". Biochemical Pharmacology.
  6. (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". Journal of Psychopharmacology.
  7. (16 March 2025). "Kᵢ Database".
  8. (February 2010). "Psychedelics and the human receptorome". PLOS ONE.
  9. (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)". Neuropharmacology.
  10. (March 2014). "Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function". Psychopharmacology.
  11. (October 2020). "In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor". Archives of Toxicology.
  12. (February 2019). "Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases". Drug Testing and Analysis.
  13. (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". The Journal of Pharmacology and Experimental Therapeutics.
  14. (August 2016). "Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens". European Neuropsychopharmacology.
  15. (May 2018). "Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs)". Neuropharmacology.
  16. (2011). "[[The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds]]". [[Transform Press]].
  17. (September 2005). "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 of Mass Spectrometry.
  18. "2C-T-2". PiHKAL.
  19. (1 July 1990). "Treatment of alcoholism". Journal of Psychoactive Drugs.
  20. (January 1991). "Central nervous system (CNS) activity of two new psychoactive compounds". Journal of Psychoactive Drugs.
  21. (3 February 2010). "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".
  22. (October 2015). "Poisons Standard October 2015". Australian Government, Department of Health, Therapeutic Goods Administration.
  23. (4 May 2016). "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". Government of Canada, Public Works and Government Services Canada, Public Services and Procurement Canada, Integrated Services Branch, Canada.
  24. (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.
  25. "Valtioneuvoston asetus huumausaineina pidettävistä aineista, valmisteista ja kasveista | 543/2008 | Lainsäädäntö | Finlex".
  26. "Förordning (1999:58) om förbud mot vissa hälsofarliga varor".
  27. "Läkemedelsverkets författningssamling". lakemedelsverket.se.
  28. "21 U.S. Code § 812 - Schedules of controlled substances".
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