2C-T-4

2C-T-4, also known as 4-isopropylthio-2,5-dimethoxyphenethylamine, is a psychedelic phenethylamine of the 2C family.^[1][2] It was first synthesized by Alexander Shulgin and is used as entheogenic recreational drug.^[1]

2C-T-4

Clinical data
Other names	4-Isopropylthio-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-isopropylthiophenethylamine
Routes of administration	Oral[1]
Drug class	Serotonin; 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Pharmacokinetic data
Duration of action	12–18 hours[1]
Identifiers
IUPAC name 2-{2,5-Dimethoxy-4-[(propan-2-yl)sulfanyl]phenyl}ethan-1-amine
CAS Number	207740-25-8 Y[chemspider]
PubChem CID	44350070
ChemSpider	21106232 Y
UNII	558WSD71D4
KEGG	C22735 Y
ChEMBL	ChEMBL338259 Y
CompTox Dashboard (EPA)	DTXSID60893915
Chemical and physical data
Formula	C13H21NO2S
Molar mass	255.38 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)Sc1cc(OC)c(cc1OC)CCN
InChI InChI=1S/C13H21NO2S/c1-9(2)17-13-8-11(15-3)10(5-6-14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3 Y Key:HDYZSVKZKDPLDT-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Effects

2C-T-4 produces psychedelic and entheogenic effects that develop slowly and can last 12 to 18 hours.^[1] While users may experience virtually no effects for the first hour after ingestion, results vary drastically between individuals and range from hallucination and euphoria to intense sickness and anxiety.^[1] Shulgin devoted a chapter in the first part of his book PiHKAL to this compound, describing an intense "plus-four" psychedelic experience mediated by a twelve milligram dose.

Interactions

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

2C drugs are metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.^[3][4] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C drugs.^[3][4][5] This may result in overdose and serious toxicity.^[5][3]

Pharmacology

2C-T-4 activities

Target	Affinity (Ki, nM)
5-HT1A	470–916
5-HT1B	ND
5-HT1D	ND
5-HT1E	ND
5-HT1F	ND
5-HT2A	27.9–54 (Ki) 5.5–220 (EC50Tooltip half-maximal effective concentration) 56–87% (EmaxTooltip maximal efficacy)
5-HT2B	ND (Ki) 63–160 (EC50) 68–75% (Emax)
5-HT2C	180–295 (Ki) ND (EC50) ND (Emax)
5-HT3	ND
5-HT4	ND
5-HT5A	ND
5-HT6	ND
5-HT7	ND
α1A	11,000
α1B, α1D	ND
α2A	130–217
α2B, α2C	ND
β1–β3	ND
D1	20,000
D2	16,000
D3	19,000
D4, D5	ND
H1	>25,000
H2–H4	ND
M1–M5	ND
I1	ND
σ1, σ2	ND
TAAR1Tooltip Trace amine-associated receptor 1	2,337–4,500 (Ki) (mouse) 19–53 (Ki) (rat) 3,700 (EC50) (mouse) 83 (EC50) (rat) >30,000 (EC50) (human) 51% (Emax) (mouse) 67% (Emax) (rat)
SERTTooltip Serotonin transporter	>30,000 (Ki) 113,000 (IC50Tooltip half-maximal inhibitory concentration) ND (EC50)
NETTooltip Norepinephrine transporter	17,000 (Ki) 134,000 (IC50) ND (EC50)
DATTooltip Dopamine transporter	>30,000 (Ki) 294,000 (IC50) ND (EC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [6][7][8][9]

2C-T-4 acts as a serotonin 5-HT₂ receptor agonist, including of the serotonin 5-HT_2A receptor.^[8][7] The mechanism that produces 2C-T-4's hallucinogenic and entheogenic effects has not been specifically established, however it is most likely to result from 5-HT_2A receptor activation in the brain, a mechanism of action shared by all of the hallucinogenic tryptamines and phenethylamines for which the mechanism of action is known.

Chemistry

2C-T-4 is the 2-carbon homolog of Aleph-4. The full chemical name is 2-[4-(isopropylthio)-2,5-dimethoxyphenyl]-ethanamine. The drug has structural and pharmacodynamic properties similar to 2C-T-7 and 2C-T-19.^{[citation needed]}

Homologue

Ψ-2C-T-4, the homologue of 2C-T-4.

2C-T-4 has a homologue, the structural isomer Ψ-2C-T-4 (2,6-dimethoxy-4-(i)-propylthiophenethylamine). This compound was tested by Alexander Shulgin at a dose of 12 mg.

At this dosage its duration was very short and it produced few effects, however based on the research into the better characterized compound Ψ-DOM, the potency of Ψ-2C-T-4 is likely to be around 1/3 that of 2C-T-4 itself, so a more effective dosage of Ψ-2C-T-4 might be in the region of 20–60 mg;^[1] however high doses such as this might well be associated with toxic side effects, and so extreme caution would be advised.

Society and culture

Popularity

2C-T-4 is relatively unknown on the black market, but has been sold to a limited extent on the research chemical market.^{[citation needed]}

Legal status

Canada

As of October 31, 2016, 2C-T-4 is a controlled substance (Schedule III) in Canada.^[10]

China

As of October 2015 2C-T-4 is a controlled substance in China.^[11]

Denmark

2C-T-4 is added to the list of Schedule B controlled substances.^[12]

Sweden

Sveriges riksdags health ministry Statens folkhälsoinstitut classified 2C-T-4 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 Jul 15, 2007, in their regulation SFS 2007:600 listed as 2,5-dimetoxi-4-isopropyltiofenetylamin (2C-T-4), making it illegal to sell or possess.^[13]

United States

As of July 9, 2012, 2C-T-4 is a Schedule I substance in the United States, under the Synthetic Drug Abuse Prevention Act of 2012.^[14]