2C-T-21
Encyclopedia
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 element
s in the structure.
thio
)-2,5-dimethoxy
phenethylamine
.
, Shulgin lists the dosage range as 8–12 mg.
who found it a very promising substance in his experiments.
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 5HT2A receptor target.
Because 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 5HT2A agonist.
, 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.
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.
Psychedelic
The term psychedelic is derived from the Greek words ψυχή and δηλοῦν , translating to "soul-manifesting". A psychedelic experience is characterized by the striking perception of aspects of one's mind previously unknown, or by the creative exuberance of the mind liberated from its ostensibly...
phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
of the 2C family. It was first synthesized by Alexander Shulgin
Alexander Shulgin
Alexander "Sasha" Theodore Shulgin is an American pharmacologist, chemist, artist, and drug developer.Shulgin is credited with the popularization of MDMA, commonly known as ecstasy, in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and...
, sometimes used as an entheogen
Entheogen
An entheogen , in the strict sense, is a psychoactive substance used in a religious, shamanic, or spiritual context. Historically, entheogens were mostly derived from plant sources and have been used in a variety of traditional religious contexts...
. It was the first psychedelic drug known to contain six different chemical element
Chemical element
A chemical element is a pure chemical substance consisting of one type of atom distinguished by its atomic number, which is the number of protons in its nucleus. Familiar examples of elements include carbon, oxygen, aluminum, iron, copper, gold, mercury, and lead.As of November 2011, 118 elements...
s in the structure.
Chemistry
The full name of 2C-T-21 is 4-(2-fluoroethylEthyl group
In chemistry, an ethyl group is an alkyl substituent derived from ethane . It has the formula -C2H5 and is very often abbreviated -Et.Ethylation is the formation of a compound by introduction of the ethyl functional group, C2H5....
thio
Thio
The prefix thio-, when applied to a chemical, such as an ion, means that an oxygen atom in the compound has been replaced by a sulfur atom. This meaning is especially valid in organic chemistry. For example, the word ether refers to an oxygen-containing compound having the general chemical...
)-2,5-dimethoxy
Methoxy
In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula O–CH3.The word is used in organic nomenclature usually to describe an ether...
phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
.
Dosage
In his book PiHKAL (Phenethylamines i Have Known And Loved)PiHKAL
PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin which was published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens...
, 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 StolaroffMyron Stolaroff
Myron J. Stolaroff is an author and researcher who is best known for his studies involving psychedelic psychotherapy. He also conducted clinical studies which attempted to measure the effects of LSD on creativity....
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-HT2A5-HT2A receptor
The mammalian 5-HT2A receptor is a subtype of the 5-HT2 receptor that belongs to the serotonin receptor family and is a G protein-coupled receptor . This is the main excitatory receptor subtype among the GPCRs for serotonin , although 5-HT2A may also have an inhibitory effect on certain areas such...
serotonin receptor
5-HT receptor
The serotonin receptors, also known as 5-hydroxytryptamine receptors or 5-HT receptors, are a group of G protein-coupled receptors and ligand-gated ion channels found in the central and peripheral nervous systems. They mediate both excitatory and inhibitory neurotransmission...
agonist
Agonist
An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...
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 5HT2A receptor target.
Because 2C-T-7, a related drug, has been shown to be a moderate monoamine oxidase
Monoamine oxidase
L-Monoamine oxidases are a family of enzymes that catalyze the oxidation of monoamines. They are found bound to the outer membrane of mitochondria in most cell types in the body. The enzyme was originally discovered by Mary Bernheim in the liver and was named tyramine 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
Serotonin syndrome
Serotonin syndrome is a potentially life-threatening adverse drug reaction that may occur following therapeutic drug use, inadvertent interactions between drugs, overdose of particular drugs, or the recreational use of certain drugs...
than other serotonergic hallucinogens, as at high doses it may slow the degradation of serotonin
Serotonin
Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...
, 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 5HT2A 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 seizureTonic-clonic seizure
Tonic–clonic seizures are a type of generalized seizure that affects the entire brain...
, 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
Operation Web Tryp
Operation Web Tryp was a United States Drug Enforcement Administration operation that ended on July 21, 2004 with the arrests of 10 persons. Its purpose was to investigate web sites suspected of distribution of unscheduled, unregulated tryptamines and phenethylamines of questionable legality...
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
Federal Analog Act
The Federal Analog Act, , is a controversial section of the United States Controlled Substances Act which allowed any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were also listed in those schedules, but only if intended for human...
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 ActFederal Analog Act
The Federal Analog Act, , is a controversial section of the United States Controlled Substances Act which allowed any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were also listed in those schedules, but only if intended for human...
because of its structural similarities to 2C-T-7
2C-T-7
2C-T-7 is a psychedelic phenethylamine of the 2C family. In his book PiHKAL: A Chemical Love Story, Alexander Shulgin lists the dosage range as 10 to 30 mg. 2C-T-7 is generally taken orally, and produces psychedelic and entactogenic effects that last 8 to 15 hours...
and its known potential to cause death. In the wake of Operation Web Tryp
Operation Web Tryp
Operation Web Tryp was a United States Drug Enforcement Administration operation that ended on July 21, 2004 with the arrests of 10 persons. Its purpose was to investigate web sites suspected of distribution of unscheduled, unregulated tryptamines and phenethylamines of questionable legality...
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.