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2C-T-2

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Pharmaceutical compound
2C-T-2
Clinical data
Other names4-Ethylthio-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-ethylthiophenethylamine
Routes of
administration
Oral [1]
Drug class Serotonin; 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Onset of action ≤1 hour[1]
Duration of action 6–8 hours[1]
Identifiers
  • 2-[4-(ethylsulfanyl)-2,5-dimethoxyphenyl]ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.241.509 Edit this at Wikidata
Chemical and physical data
Formula C12H19NO2S
Molar mass 241.35 g·mol−1
3D model (JSmol)
  • CCSc1cc(OC)c(cc1OC)CCN
  • InChI=1S/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 checkY
  • Key:HCWQGDLBIKOJPM-UHFFFAOYSA-N checkY
  (verify)

2C-T-2, also known as 4-ethylthio-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.[1] [2] [3] It was first synthesized in 1981 by Alexander Shulgin, and rated by him as one of the "magical half-dozen" most important psychedelic phenethylamines.[1] [4] [1] The drug has structural and pharmacodynamic properties similar to those of 2C-T-7 ("Blue Mystic").[1]

Use and effects

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In Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known and Loved), the dose range is listed as 12 to 25 mg orally and its duration as 6 to 8 hours.[1] Its onset is within 1 hour and peak effects occur after 1 to 2 hours.[1] The effects of 2C-T-2 have been described.[1]

Toxicity

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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, 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.[5]

Severe 'intoxication' on 2C series drugs has been observed as behavior that includes: intense hallucinations, agitation, aggression, violence, dysphoria, hypertension, tachycardia, seizures, and hyperthermia.[6]

Interactions

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2C-T-2 is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.[7] [8] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-T-2.[7] [8] [9] This may result in overdose and serious toxicity.[9] [7]

Pharmacology

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Pharmacodynamics

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2C-T-2 activities
Target Affinity (Ki, nM)
5-HT1A 370–1,740 (Ki)
3,000 (EC50 Tooltip half-maximal effective concentration)
76% (Emax Tooltip maximal efficacy)
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
H1H4 >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
TAAR1 Tooltip Trace amine-associated receptor 1 2,200 (Ki) (mouse)
40 (Ki) (rat)
96 (EC50) (mouse)
4,300 (EC50) (rat)
>10,000 (EC50) (human)
54% (Emax) (mouse)
86% (Emax) (rat)
SERT Tooltip Serotonin transporter 13,000 (Ki)
62,000 (IC50 Tooltip half-maximal inhibitory concentration)
IA (EC50)
NET Tooltip Norepinephrine transporter >30,000 (Ki)
153,000 (IC50)
IA (EC50)
DAT Tooltip Dopamine transporter >30,000 (Ki)
332,000 (IC50)
IA (EC50)
MAO-A Tooltip Monoamine oxidase A ND (IC50)
MAO-B Tooltip Monoamine oxidase B ND (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [10] [11] [12] [13] [14] [15] [16]

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,[17] a mechanism of action shared by the hallucinogenic tryptamines and phenethylamines to varying degrees.[18] [19] 2C-T-2 has also shown to be a partial agonist of adrenergic receptors.[20]

Chemistry

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Synthesis

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

Analogues

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

Society and culture

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Argentina

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2C-T-2 is also a controlled substance in Argentina as well as 2C-B and 2C-I.[21]

Australia

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2C-T-2 is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[22] 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.[22]

Canada

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As of October 31, 2016, 2C-T-2 is a controlled substance (Schedule III) in Canada.[23]

China

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As of October 2015 2C-T-2 is a controlled substance in China.[24]

Finland

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2C-T-2 is classified as a narcotic drug in Finland.[25]

Netherlands

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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

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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[26] 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.[27]

United Kingdom

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2C-T-2 and all other compounds featured in PiHKAL are illegal drugs in the United Kingdom.

United States

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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.[28]

See also

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References

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  1. ^ a b c d e f g h i j k l "#40 2C-T-2". Erowid Online Books : "PIHKAL".
  2. ^ a b c Shulgin, A.; Manning, T.; Daley, P.F. (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
  3. ^ "Stolaroff's & Well's Study". erowid.org. 2001年02月06日. Retrieved 2023年10月30日.
  4. ^ Theobald DS, Staack RF, Puetz M, Maurer HH (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. 40 (9): 1157–1172. Bibcode:2005JMSp...40.1157T. doi:10.1002/jms.890. PMID 16041763.
  5. ^ Asanuma M, Miyazaki I, Funada M (July 2020). "The neurotoxicity of psychoactive phenethylamines "2C series" in cultured monoaminergic neuronal cell lines" . Forensic Toxicology. 38 (2): 394–408. doi:10.1007/s11419-020-00527-w. ISSN 1860-8973. S2CID 211218167.
  6. ^ Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013). "2C or not 2C: phenethylamine designer drug review". Journal of Medical Toxicology. 9 (2): 172–178. doi:10.1007/s13181-013-0295-x. PMC 3657019 . PMID 23494844.
  7. ^ a b c Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013). "2C or not 2C: phenethylamine designer drug review". J Med Toxicol. 9 (2): 172–178. doi:10.1007/s13181-013-0295-x. PMC 3657019 . PMID 23494844.
  8. ^ a b Theobald DS, Maurer HH (January 2007). "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. doi:10.1016/j.bcp.2006年09月02日2. PMID 17067556.
  9. ^ a b Halman A, Kong G, Sarris J, Perkins D (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". J Psychopharmacol. 38 (1): 3–18. doi:10.1177/02698811231211219. PMC 10851641 . PMID 37982394.
  10. ^ "Ki Database". PDSP. 16 March 2025. Retrieved 16 March 2025.
  11. ^ Ray TS (February 2010). "Psychedelics and the human receptorome". PLOS ONE. 5 (2) e9019. Bibcode:2010PLoSO...5.9019R. doi:10.1371/journal.pone.0009019 . PMC 2814854 . PMID 20126400.
  12. ^ 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年08月03日4. PMID 26318099.
  13. ^ Eshleman AJ, Forster MJ, Wolfrum KM, Johnson RA, Janowsky A, Gatch MB (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 (Berl). 231 (5): 875–888. doi:10.1007/s00213-013-3303-6. PMC 3945162 . PMID 24142203.
  14. ^ Pottie E, Cannaert A, Stove CP (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". Arch Toxicol. 94 (10): 3449–3460. Bibcode:2020ArTox..94.3449P. doi:10.1007/s00204-020-02836-w. hdl:1854/LU-8687071 . PMID 32627074.
  15. ^ Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR (February 2019). "Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases". Drug Test Anal. 11 (2): 318–324. doi:10.1002/dta.2494. PMID 30188017.
  16. ^ 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. Archived from the original (PDF) on 9 May 2025.
  17. ^ 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年08月03日4. PMID 26318099. S2CID 10382311.
  18. ^ Eshleman AJ, Forster MJ, Wolfrum KM, Johnson RA, Janowsky A, Gatch MB (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. 231 (5): 875–888. doi:10.1007/s00213-013-3303-6. PMC 3945162 . PMID 24142203.
  19. ^ Rickli A, Moning OD, Hoener MC, Liechti ME (August 2016). "Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens" (PDF). European Neuropsychopharmacology. 26 (8): 1327–1337. doi:10.1016/j.euroneuro.201605001. PMID 27216487. S2CID 6685927.
  20. ^ Luethi D, Trachsel D, Hoener MC, Liechti ME (May 2018). "Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs)" (PDF). Neuropharmacology. Designer Drugs and Legal Highs. 134 (Pt A): 141–148. doi:10.1016/j.neuropharm.2017年07月01日2. PMID 28720478. S2CID 7135811.
  21. ^ "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" [DECREE 299/2010 - NATIONAL EXECUTIVE POWER (P.E.N.) Narcotics - Updating of the list and other chemical substances that must be included in the scope of Law 23,737 - Substitution of annex I of dec. 722/91] (PDF) (in Spanish). 3 February 2010. Archived from the original (PDF) on 6 July 2011.
  22. ^ a b "Poisons Standard October 2015". Federal Register of Legislation. Australian Government, Department of Health, Therapeutic Goods Administration. October 2015.
  23. ^ "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. 4 May 2016.
  24. ^ "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 Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  25. ^ "Valtioneuvoston asetus huumausaineina pidettävistä aineista, valmisteista ja kasveista | 543/2008 | Lainsäädäntö | Finlex".
  26. ^ "Förordning (1999:58) om förbud mot vissa hälsofarliga varor". www.notisum.se. Archived from the original on 2013年10月04日. Retrieved 2013年09月15日.
  27. ^ "Läkemedelsverkets författningssamling" (PDF) (in Swedish). lakemedelsverket.se.
  28. ^ "21 U.S. Code § 812 - Schedules of controlled substances". Cornell University . Retrieved 2022年12月22日.
[edit ]
Tryptamines
No ring subs.
4-Hydroxytryptamines
5-Hydroxytryptamines
5-Methoxytryptamines
Other ring subs.
α-Alkyltryptamines
Others
Cyclized
Bioisosteres
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Ψ-PEA
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  • Bioisosteres: JRT
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5-HT1
5-HT1A
  • Positive allosteric modulators: Oleamide
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3 7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
  • Negative allosteric modulators: Oleamide
TAAR1 Tooltip Trace amine-associated receptor 1
Agonists
Endogenous
Exogenous
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TAAR5 Tooltip Trace amine-associated receptor 5
Agonists
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Notes: (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as the List of trace amines, TAAR, and TAAR1 pages.
See also: Receptor/signaling modulators
Phenethylamines
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(and further-extended)
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(and close relatives)
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phenethylamines
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