2C-T-21

2C-T-21

Names
IUPAC name 2-[2,5-Dimethoxy-4-(2-fluoroethylthio)phenyl]ethanamine
Identifiers
CAS Number	207740-33-8
3D model (JSmol)	Interactive image
ChemSpider	21106231 Y
CompTox Dashboard (EPA)	DTXSID00174851
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 InChI=1/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 Key: ZBUUUKBTOCTOPW-UHFFFAOYAH
SMILES COc1cc(SCCF)c(cc1CCN)OC
Properties
Chemical formula	C12H18FNO2S
Molar mass	259.34 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

2C-T-21 is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. It was the first psychedelic drug known to contain six different chemical elements in the structure.

Chemistry

The full name of 2C-T-21 is 4-(2-fluoroethylthio)-2,5-dimethoxyphenethylamine.

Dosage

In his book PiHKAL (Phenethylamines i Have Known And Loved), Shulgin lists the dosage range as 8–12 mg.

Effects

2C-T-21 is generally taken orally, and effects typically last 7 to 14 hours. The potential psychotherapeutic applications of this chemical were explored by Myron Stolaroff who found it a very promising substance in his experiments.

Pharmacology

The mechanism that produces 2C-T-21’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. Based on the relatively high potency of 2C-T-21, it is likely that this compound binds quite strongly to the 5HT_2A receptor target.

As the 2,5-desmethoxy derivative of 2C-T-7, a related drug, has been shown to be a moderate monoamine oxidase-A inhibitor, 2C-T-21 may likewise have MAO-A inhibitory effects. This could indicate 2C-T-21 is more likely to induce serotonin syndrome than other serotonergic hallucinogens, as at high doses it may slow the degradation of serotonin, a potentially life-threatening condition.

Fluoroacetate is produced by S-dealkylation of 2C-T-21.

Overdose with 2C-T-21 has been responsible for at least one fatality, so it is likely that this drug is a relatively strong MAO-A inhibitor in addition to its action as a 5HT_2A agonist.

Dangers

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 degrees Fahrenheit (42 degrees Celsius), 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.

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.

Legality

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 "research chemical" distributor faced charges as a consequence of the death of James Downs from 2C-T-21 overdose.

External links

• 2C-T-21 Entry in PiHKAL
• 2C-T-21 Entry in PiHKAL • info
• Erowid 2C-T-21 Vault