2C-T-2

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]

2C-T-2

Clinical data
Other names	4-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	AU: S9 (Prohibited substance) BR: Class F2 (Prohibited psychotropics) CA: Schedule III US: Schedule I
Pharmacokinetic data
Onset of action	≤1 hour[1]
Duration of action	6–8 hours[1]
Identifiers
IUPAC name 2-[4-(ethylsulfanyl)-2,5-dimethoxyphenyl]ethan-1-amine
CAS Number	207740-24-7 Y
PubChem CID	12074193
ChemSpider	16787961 Y
UNII	WPS2KSX2TJ
KEGG	C22715
ChEMBL	ChEMBL339223 Y
CompTox Dashboard (EPA)	DTXSID40174850
ECHA InfoCard	100.241.509
Chemical and physical data
Formula	C12H19NO2S
Molar mass	241.35 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCSc1cc(OC)c(cc1OC)CCN
InChI 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 Y Key:HCWQGDLBIKOJPM-UHFFFAOYSA-N Y
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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]

Toxicity

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

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

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

Pharmacodynamics

2C-T-2 activities

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: [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-HT_2A, 5-HT_2B, and 5-HT_2C 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

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]

Society and culture

Legal status

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

• 2C (psychedelics)