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2C-T-2

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

2C-T-2
Names
Preferred IUPAC name
2-[4-(Ethylsulfanyl)-2,5-dimethoxyphenyl]ethan-1-amine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.241.509 Edit this at Wikidata
KEGG
UNII
  • 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
  • InChI=1/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
    Key: HCWQGDLBIKOJPM-UHFFFAOYAX
  • CCSc1cc(OC)c(cc1OC)CCN
Properties
C12H19NO2S
Molar mass 241.35 g/mol
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302
P264, P270, P301+P312, P330, P501
Pharmacology
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Dosage

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In Alexander Shulgin's book PiHKAL, the dosage range is listed as 12 to 25 mg.[3]

Pharmacology

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The mechanism of action that produces 2C-T-2’s hallucinogenic and entheogenic effects is shown to be most likely a result from action as a 5-HT2A, 5-HT2B, and 5-HT2C serotonin receptor agonist,[4] a mechanism of action shared by the hallucinogenic tryptamines and phenethylamines to varying degrees.[5][6] 2C-T-2 has also shown to be a partial agonist of adrenergic receptors.[7]

Dangers

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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.[8] This has also been shown to be magnified in serotonergic-containing cells with combined use of 2C series drugs with alcohol, MDMA, and methamphetamine.[9]

Severe 'intoxication' on 2C series drugs has been observed as behavior that includes: intense hallucinations, agitation, aggression, violence, dysphoria, hypertension, tachycardia, seizures, and hyperthermia.[10]

Drug prohibition laws

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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.[11]

Canada

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As of October 31, 2016, 2C-T-2 is a controlled substance (Schedule III) in Canada.[12]

China

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As of October 2015 2C-T-2 is a controlled substance in China.[13]

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[14] 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.[15]

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.[16]

Australia

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2C-T-2 is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[17] 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.[17]

References

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  1. ^ "Stolaroff's & Well's Study". erowid.org. 2001-02-06. Retrieved 2023-10-30.
  2. ^ 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.
  3. ^ a b "#40 2C-T-2". Erowid Online Books : "PIHKAL".
  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)" (PDF). Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099. S2CID 10382311.
  5. ^ 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.
  6. ^ 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.2016.05.001. PMID 27216487. S2CID 6685927.
  7. ^ 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.2017.07.012. PMID 28720478. S2CID 7135811.
  8. ^ Dai, Chongshan; Xiao, Xilong; Sun, Feifei; Zhang, Yuan; Hoyer, Daniel; Shen, Jianzhong; Tang, Shusheng; Velkov, Tony (2019-11-30). "T-2 toxin neurotoxicity: role of oxidative stress and mitochondrial dysfunction". Archives of Toxicology. 93 (11): 3041–3056. doi:10.1007/s00204-019-02577-5. ISSN 1432-0738. PMID 31570981. S2CID 203592638.
  9. ^ 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.
  10. ^ 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.
  11. ^ "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.
  12. ^ "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.
  13. ^ "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.
  14. ^ "Förordning (1999:58) om förbud mot vissa hälsofarliga varor". www.notisum.se. Archived from the original on 2013-10-04. Retrieved 2013-09-15.
  15. ^ "Läkemedelsverkets författningssamling" (PDF) (in Swedish). lakemedelsverket.se.
  16. ^ "21 U.S. Code § 812 - Schedules of controlled substances". Cornell University. Retrieved 2022-12-22.
  17. ^ a b "Poisons Standard October 2015". Federal Register of Legislation. Australian Government, Department of Health, Therapeutic Goods Administration. October 2015.
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