2C-T-21

2C-T-21, also known as 4-(2-fluoroethylthio)-2,5-dimethoxyphenethylamine, is a psychedelic phenethylamine of the 2C family.^[1] It is taken orally.^[1]

2C-T-21

Clinical data
Other names	4-(2-Fluoroethylthio)-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-(2-fluoroethylthio)phenethylamine; 2C-T-FE
Routes of administration	Oral[1]
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Legal status
Legal status	In general unscheduled
Pharmacokinetic data
Onset of action	15 min–1 hour[1]
Duration of action	7–10 hours[1]
Identifiers
IUPAC name 2-{{#parsoidfragment:3}}{4-[(2-fluoroethyl)sulfanyl]-2,5-dimethoxyphenyl}ethan-1-amine
CAS Number	207740-33-8 Y[chemspider]
PubChem CID	44349972
ChemSpider	21106231 Y
UNII	720O3Q04GA
ChEMBL	ChEMBL126582 Y
CompTox Dashboard (EPA)	DTXSID00174851
Chemical and physical data
Formula	C12H18FNO2S
Molar mass	259.34 g·mol−1
3D model (JSmol)	Interactive image
SMILES COc1cc(SCCF)c(cc1CCN)OC
InChI InChI=1S/C12H18FNO2S/c1-15-10-8-12(17-6-4-13)11(16-2)7-9(10)3-5-14/h7-8H,3-6,14H2,1-2H3 Y Key:ZBUUUKBTOCTOPW-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

2C-T-21 was first described in the scientific literature by Alexander Shulgin and colleagues in 1991.^[2] 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 the dose range as 8 to 12 mg orally and its duration as 7 to 10 hours.^[1] Its onset is described as 15 minutes to 1 hour and peak effects occur after 1 to 2 hours.^[1] The effects of 2C-T-21 have been described.^[1]

Toxicity

On March 9, 2004, a 22-year-old quadriplegic man named James Edwards Downs in St. Francisville, Louisiana, consumed an unknown dose of 2C-T-21 by sticking his tongue into a vial of powder he had purchased online. He developed a temperature of 108 °F (42 °C),^[3] had a tonic-clonic seizure, and slipped into a coma. Four days later, on March 13, Downs died at Lane Memorial Hospital in Zachary, LA.^{[citation needed]}

This death became part of a two-year DEA investigation called Operation Web Tryp which was launched in 2002. On July 22, 2004, the owners of American Chemical Supply were arrested on federal charges relating to distribution of controlled substance analogues and the death of James Edwards Downs. Little is known about the toxicity of 2C-T-21 beyond this incident.

Interactions

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

Pharmacology

Pharmacodynamics

2C-T-21 shows high affinity for the serotonin 5-HT_2A receptor (K_i = 27 nM).^[4] It produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.^[4]

Chemistry

Synthesis

The chemical synthesis of 2C-T-21 has been described.^[1]

Analogues

Analogues of 2C-T-21 include 2C-T-2, 2C-T-21.5, and 2C-T-22, among others.^[4][1][5]

History

2C-T-21 was first described in the scientific literature by Alexander Shulgin and colleagues in a journal article in 1991.^[2] Shortly thereafter, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1] The potential applications of 2C-T-21 in psychedelic-assisted psychotherapy were explored by Myron Stolaroff.^[6]

Society and culture

Legal status

2C-T-21 is unscheduled and uncontrolled in the United States, but possession and sales of 2C-T-21 would probably be prosecuted under the Federal Analog Act because of its structural similarities to 2C-T-7 and its known potential to cause death. In the wake of Operation Web Tryp in July 2004, at least one distributor faced charges as a consequence of the death of James Downs from 2C-T-21 overdose.

Canada

As of October 31, 2016, 2C-T-21 is a controlled substance (Schedule III) in Canada.^[7]

See also

• 2C (psychedelics)