2C-T-4

2C-T-4
Names
	Preferred IUPAC name 2-{2,5-Dimethoxy-4-[(propan-2-yl)sulfanyl]phenyl}ethan-1-amine
Identifiers
CAS Number	207740-25-8 [chemspider];
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL338259 ;
ChemSpider	21106232 ;
KEGG	C22735 ;
PubChem CID	44350070;
UNII	558WSD71D4 ;
CompTox Dashboard (EPA)	DTXSID60893915 ;
	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 Key: HDYZSVKZKDPLDT-UHFFFAOYSA-N ; InChI=1/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 Key: HDYZSVKZKDPLDT-UHFFFAOYAR;
	SMILES CC(C)Sc1cc(OC)c(cc1OC)CCN;
Properties
Chemical formula	C13H21NO2S
Molar mass	255.38 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

2C-T-4 (2,5-dimethoxy-4-isopropylthiophenethylamine) is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and is used as entheogenic recreational drug.

Chemistry

2C-T-4 is the 2-carbon homolog of aleph-4. The full chemical name is 2-[4-(isopropyl thio)-2,5-dimethoxy phenyl]-ethan amine. The drug has structural and pharmacodynamic properties similar to 2C-T-7 and 2C-T-19.^{[citation needed]}

Effects

2C-T-4 produces psychedelic and entheogenic effects that develop slowly and can last 8–16 hours.^{[medical citation needed]} 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.

Pharmacology

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 action as a 5-HT_2A serotonin receptor agonist in the brain, a mechanism of action shared by all of the hallucinogenic tryptamines and phenethylamines for which the mechanism of action is known.

Popularity

2C-T-4 is relatively unknown on the black market, but has been sold to a limited extent on the research chemical market.

Drug prohibition laws

Canada

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

China

As of October 2015 2C-T-4 is a controlled substance in China.^[3]

Denmark

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

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.^[5]

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.^[6]

Homologue

2C-T-4 has one 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.

References

^ ^a ^b Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
^ "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016.
^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
^ "Retsinformation".
^ Larsson, Maria. "Svensk författningssamling" (PDF). Retrieved January 24, 2022.
^ Portman. "Synthetic Drug Abuse Prevention Act of 2012". Govtrack. Retrieved 22 July 2012.

External links

[CitePiHKAL-1] Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.

[2] "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016.

[3] "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.

[4] "Retsinformation".

[5] Larsson, Maria. "Svensk författningssamling" (PDF). Retrieved January 24, 2022.

[6] Portman. "Synthetic Drug Abuse Prevention Act of 2012". Govtrack. Retrieved 22 July 2012.

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Names


Preferred IUPAC name 2-{2,5-Dimethoxy-4-[(propan-2-yl)sulfanyl]phenyl}ethan-1-amine
Identifiers
CAS Number	207740-25-8^{Y[chemspider]}
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL338259^Y
ChemSpider	21106232^Y
KEGG	C22735^Y
PubChem CID	44350070
UNII	558WSD71D4^N
CompTox Dashboard (EPA)	DTXSID60893915
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 InChI=1/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 Key: HDYZSVKZKDPLDT-UHFFFAOYAR
SMILES CC(C)Sc1cc(OC)c(cc1OC)CCN
Properties
Chemical formula	C₁₃H₂₁NO₂S
Molar mass	255.38 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references