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| Other names | 4-Ethylthio-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-ethylthiophenethylamine |
| Routes of administration | Oral[1] |
| Drug class | Serotonin;5-HT2 receptoragonist;Serotonergic psychedelic;Hallucinogen |
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| Pharmacokinetic data | |
| Onset of action | ≤1 hour[1] |
| Duration of action | 6–8 hours[1] |
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| ECHA InfoCard | 100.241.509 |
| Chemical and physical data | |
| Formula | C12H19NO2S |
| Molar mass | 241.35 g·mol−1 |
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2C-T-2, also known as4-ethylthio-2,5-dimethoxyphenethylamine, is apsychedelic drug of thephenethylamine and2C families.[1][2][3] It is takenorally.[1]
The drug acts as aserotonin5-HT2 receptoragonist, including of the serotonin5-HT2A receptor.[4][5][6][7]
2C-T-2 was discovered byAlexander Shulgin in 1981 and was first described in thescientific literature byMyron Stolaroff in 1990.[8][9][10][1]
InAlexander Shulgin's bookPiHKAL (Phenethylamines I Have Known and Loved), the dose range is listed as 12 to 25 mgorally and itsduration as 6 to 8 hours.[1] Itsonset 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 withmescaline,2C-B,2C-T-7, and others.[1]
A potential risk ofneurotoxicity from 2C-T-2 use (and 2C chemical series in general) has been shown in serotonergic anddopaminergic 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, andmethamphetamine.[11]
Severe 'intoxication' on 2C series drugs has been observed as behavior that includes: intensehallucinations, agitation, aggression, violence,dysphoria,hypertension,tachycardia,seizures, andhyperthermia.[12]
2C-T-2 ismetabolized by themonoamine oxidase (MAO)enzymesMAO-A andMAO-B.[12][13]Monoamine oxidase inhibitors (MAOIs) such asphenelzine,tranylcypromine,moclobemide, andselegiline may potentiate the effects of 2C-T-2.[12][13][14] This may result inoverdose and serioustoxicity.[14][12]
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 370–1,740 (Ki) 3,000 (EC50Tooltip half-maximal effective concentration) 76% (EmaxTooltip 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 |
| TAAR1Tooltip 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) |
| SERTTooltip Serotonin transporter | 13,000 (Ki) 62,000 (IC50Tooltip half-maximal inhibitory concentration) IA (EC50) |
| NETTooltip Norepinephrine transporter | >30,000 (Ki) 153,000 (IC50) IA (EC50) |
| DATTooltip Dopamine transporter | >30,000 (Ki) 332,000 (IC50) IA (EC50) |
| MAO-ATooltip Monoamine oxidase A | ND (IC50) |
| MAO-BTooltip 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:[15][4][5][6][7][16][17] | |
2C-T-2 acts as aserotonin5-HT2 receptoragonist, including of the serotonin5-HT2A and5-HT2C receptors.[4][5][6][7] Themechanism of action that produces 2C-T-2'shallucinogenic effects is shown to be most likely a result from action as aserotonin5-HT2A,5-HT2B, and5-HT2Cserotonin receptoragonist,[5] a mechanism of action shared by the psychedelictryptamines andphenethylamines to varying degrees.[6][18] 2C-T-2 has also shown to be apartial agonist ofadrenergic receptors.[19]
Thechemical synthesis of 2C-T-2 has been described.[1][2]
Analogues of 2C-T-2 include2C-T (2C-T-1),2C-T-4,2C-T-7,Aleph-2, and25T2-NBOMe, among others.[1][2]
2C-T-2 was firstsynthesized byAlexander Shulgin in 1981.[8] He discovered its psychedelic effects that same year.[20] The drug was first described in thescientific literature byMyron Stolaroff in 1990.[9] Subsequently, it was described in greater detail in a 1991 publication by Shulgin and colleagues[10] and in his 1991 bookPiHKAL (Phenethylamines I Have Known and Loved).[1] Following this, 2C-T-2 emerged as a noveldesigner drug in the 1990s.[8]
2C-T-2 is also a controlled substance in Argentina as well as2C-B and2C-I.[21]
2C-T-2 is considered a Schedule 9 prohibited substance in Australia under thePoisons 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]
As of October 31, 2016, 2C-T-2 is a controlled substance (Schedule III) in Canada.[23]
As of October 2015 2C-T-2 is a controlled substance in China.[24]
2C-T-2 is classified as a narcotic drug in Finland.[25]
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 theOpium Law.
Schedule I in Sweden. 2C-T-2 was first classified as "health hazard" under the actLagen om förbud mot vissa hälsofarliga varor (translatedAct 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 toNarcotic Drugs Punishments Act underSwedish schedule I ("substances, plant materials and fungi which normally do not have medical use") as of March 16, 2004, published byMedical Products Agency (MPA) in regulationLVFS 2004:3 listed as 2C-T-2, 2,5-dimetoxi-4-etyltiofenetylamin.[27]
2C-T-2 and all other compounds featured inPiHKAL are illegal drugs in theUnited Kingdom.
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]
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
