2C-T-4

2C-T-4, also known as 4-isopropylthio-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.^[1][2] It is taken orally.^[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
Onset of action	30 minutes–2 hours[1] Peak: 3 hours[1]
Duration of action	12–18 hours[1]
Identifiers
IUPAC name 2-{{#parsoidfragment: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)

2C-T-4 was first described in the scientific literature by Alexander Shulgin and colleagues in 1991.^[3] Shortly after this, Shulgin described 2C-T-17 in greater detail in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 2C-T-4's dose range as 8 to 20 mg orally and its duration as 12 to 18 hours.^[1] Its onset is 30 minutes to 2 hours and peak effects occur after 3 hours.^[1] The effects of 2C-T-4 have been described and include psychedelic visuals among others.^[1] Shulgin devoted a chapter in the first part of PiHKAL to 2C-T-4, describing an intense "plus-four" experience on the Shulgin Rating Scale with a 12 mg dose.^[1]

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.^[4][5] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C drugs.^[4][5][6] This may result in overdose and serious toxicity.^[6][4]

Pharmacology

Pharmacodynamics

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: [7][8][9][10]

2C-T-4 acts as a serotonin 5-HT₂ receptor agonist, including of the serotonin 5-HT_2A receptor.^[9][8] The mechanism that produces 2C-T-4's hallucinogenic 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 homologue of Aleph-4.^[1] The full chemical name is 2-[4-(isopropylthio)-2,5-dimethoxyphenyl]-ethanamine.^[1] The drug has structural and pharmacodynamic properties similar to 2C-T-7 and 2C-T-19.^[1] A notable analogue of 2C-T-4 is the Ψ-PEA compound Ψ-2C-T-4.^[1]

Synthesis

The chemical synthesis of 2C-T-4 has been described.^[1]

History

2C-T-4 was first described in the scientific literature by Alexander Shulgin and colleagues in a journal article in 1991.^[3] Shortly thereafter, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1]

Society and culture

Legal status

Canada

As of October 31, 2016, 2C-T-4 is a controlled substance (Schedule III) in Canada.^[11]

China

As of October 2015 2C-T-4 is a controlled substance in China.^[12]

Denmark

2C-T-4 is added to the list of Schedule B controlled substances.^[13]

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.^[14]

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.^[15]

See also

• 2C (psychedelics)