2C-T-2
2C-T-2, also known as 4-ethylthio-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.<ref name="PiHKAL">Template:CitePiHKAL http://www.erowid.org/library/books_online/pihkal/pihkal040.shtml</ref><ref name="ShulginManningDaley2011" /><ref name="Murple2001">Template:Cite web</ref> It is taken orally.<ref name="PiHKAL" />
The drug acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A receptor.<ref name="Ray2010" /><ref name="RickliLuethiReinisch2015" /><ref name="EshlemanForsterWolfrum2014" /><ref name="PottieCannaertStove2020" />
2C-T-2 was discovered by Alexander Shulgin in 1981 and was first described in the scientific literature by Myron Stolaroff in 1990.<ref name="TheobaldStaackPuetz2005" /><ref name="Stolaroff1990" /><ref name="ShulginShulginJacob1991" /><ref name="PiHKAL" />
Use and effects
In Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known and Loved), the dose range is listed as 12 to 25Template:Nbspmg orally and its duration as 6 to 8Template:Nbsphours.<ref name="PiHKAL" /> Its onset is within 1Template:Nbsphour and peak effects occur after 1 to 2Template:Nbsphours.<ref name="PiHKAL" /> The effects of 2C-T-2 have been described.<ref name="PiHKAL" /> Shulgin rated it as one of the "magical half-dozen" most important psychedelic phenethylamines, along with mescaline, 2C-B, 2C-T-7, and others.<ref name="PiHKAL" />
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.<ref>Template:Cite journal</ref>
Severe 'intoxication' on 2C series drugs has been observed as behavior that includes: intense hallucinations, agitation, aggression, violence, dysphoria, hypertension, tachycardia, seizures, and hyperthermia.<ref>Template:Cite journal</ref>
Interactions
2C-T-2 is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.<ref name="DeanStellpflugBurnett2013">Template:Cite journal</ref><ref name="TheobaldMaurer2007">Template:Cite journal</ref> Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-T-2.<ref name="DeanStellpflugBurnett2013" /><ref name="TheobaldMaurer2007" /><ref name="HalmanKongSarris2024">Template:Cite journal</ref> This may result in overdose and serious toxicity.<ref name="HalmanKongSarris2024" /><ref name="DeanStellpflugBurnett2013" />
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 370–1,740 (Ki) 3,000 (Template:Abbrlink) 76% (Template:Abbrlink) |
| 5-HT1B | 858 |
| 5-HT1D | 86 |
| 5-HT1E | 415 |
| 5-HT1F | Template:Abbr |
| 5-HT2A | 9–40 (Ki) 0.354–80 (Template:Abbr) 67–107% (Template:Abbr) |
| 5-HT2B | 6–69 (Ki) 130 (Template:Abbr) 75% (Template:Abbr) |
| 5-HT2C | 14–54 (Ki) 0.0233–3.8 (Template:Abbr) 87–107% (Template:Abbr) |
| 5-HT3 | >10,000 |
| 5-HT4 | Template:Abbr |
| 5-HT5A | >10,000 |
| 5-HT6 | 1,362 |
| 5-HT7 | 969 |
| α1A | 17,000 |
| α1B | >10,000 |
| α1D | Template:Abbr |
| α2A | 230–730 |
| α2B | 982 |
| α2C | 166 |
| β1 | 9,202 |
| β2 | 1,184 |
| β3 | Template:Abbr |
| 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 |
| Template:Abbrlink | 2,200 (Ki) (mouse) 40 (Ki) (rat) 96 (Template:Abbr) (mouse) 4,300 (Template:Abbr) (rat) >10,000 (Template:Abbr) (human) 54% (Template:Abbr) (mouse) 86% (Template:Abbr) (rat) |
| Template:Abbrlink | 13,000 (Ki) 62,000 (Template:Abbrlink) Template:Abbr (Template:Abbr) |
| Template:Abbrlink | >30,000 (Ki) 153,000 (Template:Abbr) Template:Abbr (Template:Abbr) |
| Template:Abbrlink | >30,000 (Ki) 332,000 (Template:Abbr) Template:Abbr (Template:Abbr) |
| Template:Abbrlink | Template:Abbr (Template:Abbr) |
| Template:Abbrlink | Template:Abbr (Template:Abbr) |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: <ref name="PDSPKiDatabase">Template:Cite web</ref><ref name="Ray2010">Template:Cite journal</ref><ref name="RickliLuethiReinisch2015">Template:Cite journal</ref><ref name="EshlemanForsterWolfrum2014">Template:Cite journal</ref><ref name="PottieCannaertStove2020">Template:Cite journal</ref><ref name="WagmannBrandtStratford2019">Template:Cite journal</ref><ref name="SimmlerBuchyChaboz2016">Template:Cite journal</ref> | |
2C-T-2 acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A and 5-HT2C receptors.<ref name="Ray2010" /><ref name="RickliLuethiReinisch2015" /><ref name="EshlemanForsterWolfrum2014" /><ref name="PottieCannaertStove2020" /> 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,<ref name="RickliLuethiReinisch2015" /> a mechanism of action shared by the psychedelic tryptamines and phenethylamines to varying degrees.<ref name="EshlemanForsterWolfrum2014" /><ref name="RickliMoningHoener2016">Template:Cite journal</ref> 2C-T-2 has also shown to be a partial agonist of adrenergic receptors.<ref name="LuethiTrachselHoener2018">Template:Cite journal</ref>
Chemistry
Synthesis
The chemical synthesis of 2C-T-2 has been described.<ref name="PiHKAL" /><ref name="ShulginManningDaley2011">Template:Cite book</ref>
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.<ref name="PiHKAL" /><ref name="ShulginManningDaley2011" />
History
2C-T-2 was first synthesized by Alexander Shulgin in 1981.<ref name="TheobaldStaackPuetz2005">Template:Cite journal</ref> He discovered its psychedelic effects that same year.<ref name="Shulgin1981">https://isomerdesign.com/pihkal/notebooks/transcripts/p4/p4.474.pdf</ref> The drug was first described in the scientific literature by Myron Stolaroff in 1990.<ref name="Stolaroff1990">Template:Cite journal</ref> Subsequently, it was described in greater detail in a 1991 publication by Shulgin and colleagues<ref name="ShulginShulginJacob1991">Template:Cite journal</ref> and in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).<ref name="PiHKAL" /> Following this, 2C-T-2 emerged as a novel designer drug in the 1990s.<ref name="TheobaldStaackPuetz2005" />
Society and culture
Legal status
Argentina
2C-T-2 is also a controlled substance in Argentina as well as 2C-B and 2C-I.<ref>Template:Cite web</ref>
Australia
2C-T-2 is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).<ref name="Poisons Standard">Template:Cite web</ref> 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.<ref name="Poisons Standard" />
Canada
As of October 31, 2016, 2C-T-2 is a controlled substance (Schedule III) in Canada.<ref>Template:Cite web</ref>
China
As of October 2015 2C-T-2 is a controlled substance in China.<ref>Template:Cite web</ref>
Finland
2C-T-2 is classified as a narcotic drug in Finland.<ref>Template:Cite web</ref>
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<ref>Template:Cite web</ref> 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.<ref>Template:Cite web</ref>
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.<ref>Template:Cite web</ref>
See also
References
External links
- 2C-T-2 - Isomer Design
- 2C-T-2 - PsychonautWiki
- 2C-T-2 - Erowid
- 2C-T-2 - PiHKAL - Erowid
- 2C-T-2 - PiHKAL - Isomer Design
- 2C-T-2: Potential Therapeutic Alternative to MDMA? - Tripsitter
- Sulfurous Samadhi: An Investigation of 2C-T-2 & 2C-T-7 - Erowid
Template:Psychedelics Template:Serotonin receptor modulators Template:TAAR modulators Template:Phenethylamines