2C-T-2

Last updated

2C-T-2
2C-T-2 2DACS.svg
2C-T-2 3D.png
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 OOjs UI icon edit-ltr-progressive.svg
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 Yes check.svgY
  • Key:HCWQGDLBIKOJPM-UHFFFAOYSA-N Yes check.svgY
   (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 is taken orally. [1]

Contents

The drug acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A receptor. [4] [5] [6] [7]

2C-T-2 was discovered by Alexander Shulgin in 1981 and was first described in the scientific literature by Myron Stolaroff in 1990. [8] [9] [10] [1]

Use and effects

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] Shulgin rated it as one of the "magical half-dozen" most important psychedelic phenethylamines, along with mescaline, 2C-B, 2C-T-7, and others. [1]

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. [11]

Severe 'intoxication' on 2C series drugs has been observed as behavior that includes: intense hallucinations, agitation, aggression, violence, dysphoria, hypertension, tachycardia, seizures, and hyperthermia. [12]

Interactions

2C-T-2 is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B. [12] [13] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-T-2. [12] [13] [14] This may result in overdose and serious toxicity. [14] [12]

Pharmacology

Pharmacodynamics

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
H1–H4 >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 12,200 (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 transporter13,000 (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 AND (IC50)
MAO-B Tooltip Monoamine oxidase BND (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [15] [4] [5] [6] [7] [16] [17]

2C-T-2 acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A and 5-HT2C receptors. [4] [5] [6] [7] 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, [5] a mechanism of action shared by the psychedelic tryptamines and phenethylamines to varying degrees. [6] [18] 2C-T-2 has also shown to be a partial agonist of adrenergic receptors. [19]

Chemistry

Synthesis

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

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. [1] [2]

History

2C-T-2 was first synthesized by Alexander Shulgin in 1981. [8] He discovered its psychedelic effects that same year. [20] The drug was first described in the scientific literature by Myron Stolaroff in 1990. [9] Subsequently, it was described in greater detail in a 1991 publication by Shulgin and colleagues [10] and in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). [1] Following this, 2C-T-2 emerged as a novel designer drug in the 1990s. [8]

Society and culture

Argentina

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

Australia

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

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

China

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

Finland

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

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 [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

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. [28]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 Shulgin A, Shulgin A (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/pihkal040.shtml
  2. 1 2 3 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.
  3. ↑ Murple (6 February 2001). "Sulfurous Samadhi: Stolaroff's & Well's Study". erowid.org.
  4. 1 2 3 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.
  5. 1 2 3 4 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)". Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID   26318099.
  6. 1 2 3 4 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.
  7. 1 2 3 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". Archives of Toxicology. 94 (10): 3449–3460. Bibcode:2020ArTox..94.3449P. doi:10.1007/s00204-020-02836-w. hdl: 1854/LU-8687071 . PMID   32627074.
  8. 1 2 3 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. 2,5-Dimethoxy-4-ethylthio-β-phenethylamine (2C-T-2) was first synthesized as a new designer drug in 1981 by Alexander Shulgin. In the 1980s, 2C-T-2 was not a common drug of abuse; it started to become popular only in the 1990s after it was mentioned in Shulgin's compilation 'PIHKAL' in 1991, and especially in the late 1990s when it was sold in so-called 'Smart Shops' in the Netherlands. It has surfaced in the illicit drug market in the form of tablets containing 2C-T-2 alone or in mixtures with other designer drugs.2,3 During 2000/2001, several fatalities related to another substance of this group were reported.4,5 Because of the increasing problems with 2C-T-2, it was included in the lists of controlled substances of many countries.6
  9. 1 2 Clifford JS, Baldwin N, Brett J, Cerbo L, Demers-Gendreau C (1 July 1990). "Treatment of alcoholism". Journal of Psychoactive Drugs. 22 (3): 377. doi:10.1080/02791072.1990.10472568. PMID   2286872.
  10. 1 2 Shulgin AT, Shulgin A, Jacob P (January 1991). "Central nervous system (CNS) activity of two new psychoactive compounds". Journal of Psychoactive Drugs. 23 (1): 95–96. doi:10.1080/02791072.1991.10472583. eISSN   2159-9777. PMID   1941371. Archived from the original on 2025-07-13.
  11. ↑ 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.
  12. 1 2 3 4 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.
  13. 1 2 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)". Biochemical Pharmacology. 73 (2): 287–297. doi:10.1016/j.bcp.2006.09.022. PMID   17067556.
  14. 1 2 Halman A, Kong G, Sarris J, Perkins D (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". Journal of Psychopharmacology. 38 (1): 3–18. doi:10.1177/02698811231211219. PMC   10851641 . PMID   37982394.
  15. ↑ "Kᵢ Database". PDSP. 16 March 2025. Retrieved 16 March 2025.
  16. ↑ 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 Testing and Analysis. 11 (2): 318–324. doi:10.1002/dta.2494. PMID   30188017.
  17. ↑ 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). The Journal of Pharmacology and Experimental Therapeutics. 357 (1): 134–144. doi:10.1124/jpet.115.229765. PMID   26791601. Archived from the original (PDF) on 9 May 2025.
  18. ↑ Rickli A, Moning OD, Hoener MC, Liechti ME (August 2016). "Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens". European Neuropsychopharmacology. 26 (8): 1327–1337. doi:10.1016/j.euroneuro.2016.05.001. PMID   27216487. S2CID   6685927.
  19. ↑ Luethi D, Trachsel D, Hoener MC, Liechti ME (May 2018). "Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs)". Neuropharmacology. Designer Drugs and Legal Highs. 134 (Pt A): 141–148. doi:10.1016/j.neuropharm.2017.07.012. PMID   28720478. S2CID   7135811.
  20. ↑ "2C-T-2" (PDF). PiHKAL.
  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. 1 2 "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 2013-10-04. Retrieved 2013-09-15.
  27. ↑ "Läkemedelsverkets författningssamling" (PDF) (in Swedish). lakemedelsverket.se.
  28. ↑ "21 U.S. Code § 812 - Schedules of controlled substances". Cornell University . Retrieved 2022-12-22.
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