2C-T, or 2C-T-1, also known as 4-methylthio-2,5-dimethoxyphenethylamine, is a

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...

and

hallucinogenic drug Hallucinogens, also known as psychedelics, entheogens, or historically as psychotomimetics, are a large and diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, moo ...

of the

2C family 2C (2C-''x'') is a general name for the family of psychedelic phenethylamines containing methoxy groups on the 2 and 5 positions of a benzene ring. Most of these compounds also carry lipophilic substituents at the 4 position, usually resulting ...

. It is used by some as an

entheogen Entheogens are psychoactive substances used in spiritual and religious contexts to induce altered states of consciousness. Hallucinogens such as the psilocybin found in so-called "magic" mushrooms have been used in sacred contexts since ancie ...

. It has structural and pharmacodynamic properties similar to the drugs

mescaline Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a natural product, naturally occurring psychedelic drug, psychedelic alkaloid, protoalkaloid of the substituted phenethylamine class, found ...

and

2C-T-2 2C-T-2, also known as 4-ethylthio-2,5-dimethoxyphenethylamine, is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin, and rated by him as one of the "magical half-dozen" most ...

Effects

In ''

TiHKAL ''TiHKAL: The Continuation'' is a 1997 book written by Alexander Shulgin and Ann Shulgin about a family of psychoactive drugs known as tryptamines. A sequel to '' PiHKAL: A Chemical Love Story'', ''TiHKAL'' is an acronym that stands for "Trypt ...

'',

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

lists a dose range of 60 to 100mg and a duration of 3 to 5hours for 2C-T.2C-T Entry in PiHKAL
/ref> It produces

and

MDMA 3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an empathogen–entactogenic drug with stimulant and minor Psychedelic drug, psychedelic properties. In studies, it has been used ...

-like effects.

Interactions

Pharmacology

2C-T shows

affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Pa ...

for the

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

5-HT₂ receptors and is known to act as an

agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

of the serotonin 5-HT_2A and 5-HT_2B receptors. The mechanism that produces 2C-T's hallucinogenic and entheogenic effects has not been specifically established, however it is most likely to result from serotonin 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. 2C-T shows no affinity for the

monoamine transporter Monoamine transporters (MATs) are proteins that function as integral Cell membrane, plasma-membrane Neurotransmitter transporter, transporters to regulate concentrations of extracellular monoamine neurotransmitters. The three major classes are se ...

Chemistry

2C-T is in a class of compounds commonly known as

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...

s, and is the 4-

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...

thio analogue of

2C-O 2C-O, also known as 2,4,5-trimethoxyphenethylamine (2,4,5-TMPEA) or TMPEA-2, is a chemical compound of the phenethylamine and 2C families. It is a positional isomer of mescaline (3,4,5-trimethoxyphenethylamine) and is the α-desmethyl analogue o ...

, a

positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...

of mescaline. It is also the 2C analog of

Aleph Aleph (or alef or alif, transliterated ʾ) is the first Letter (alphabet), letter of the Semitic abjads, including Phoenician alphabet, Phoenician ''ʾālep'' 𐤀, Hebrew alphabet, Hebrew ''ʾālef'' , Aramaic alphabet, Aramaic ''ʾālap'' � ...

. The systematic name of the chemical is 2-(2,5-di

methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

-4-(

thio)

phenyl In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph (archaically φ) or Ø. The phenyl group is closely related to benzene and can be viewed as a benzene ...

)ethanamine. The CAS number of 2C-T is 61638-09-3.

Derivatives

A large number of

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

s of 2C-T have been developed and described. These include

2C-T-3 2C-T-3, also initially numbered as 2C-T-20 and also known as 4-methallylthio-2,5-dimethoxyphenethylamine, is a lesser-known psychedelic drug related to compounds such as 2C-T-7 and 2C-T-16. It was named by Alexander Shulgin but was never made or t ...

2C-T-4 2C-T-4, also known as 4-isopropylthio-2,5-dimethoxyphenethylamine, is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and is used as entheogenic recreational drug. Effects 2C-T-4 produces psychedelic ...

2C-T-7 2C-T-7, also known as 4-propylthio-2,5-dimethoxyphenethylamine, is a psychedelic phenethylamine of the 2C family. In his book '' PiHKAL: A Chemical Love Story'', Alexander Shulgin lists the dosage range as 10–30 mg. 2C-T-7 is generall ...

, and

2C-T-16 2C-T-16, also known as 4-allylthio-2,5-dimethoxyphenethylamine, is a lesser-known psychedelic drug. It was originally named by Alexander Shulgin as described in his book PiHKAL (Phenethylamines i Have Known And Loved), however while Shulgin bega ...

, among others.

History

2C-T was first synthesized and studied through a collaboration between

David E. Nichols David Earl Nichols (born December 23, 1944, Covington, Kentucky) is an American pharmacologist and medicinal chemist. Previously the Robert C. and Charlotte P. Anderson Distinguished Chair in Pharmacology at Purdue University, Nichols has worke ...

and

. It was first described in the

scientific literature Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical ...

in 1976.

Society and culture

Popularity

2C-T is almost unknown on the black market although it has rarely been sold by "research chemical" companies. Limited accounts of 2C-T can be found in the book ''

PiHKAL ''PiHKAL: A Chemical Love Story'' is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is Psychoactive drug, psychoactive phenethylamine Derivative (chemistry), chemical derivatives, notably those that act ...

''.

Legal status

Canada

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

United States

2C-T is unscheduled and unregulated in the

United States The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...

; however its close similarity in structure and effects to

could potentially subject possession and sale of 2C-T to prosecution under the

Federal Analog Act The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed ...

. This seems to be the tack the federal government is taking in the wake of the DEA's

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 tryptamine ...

. A series of court cases in the US involving the prosecution of several online vendors were commenced in 2004 and resulted in a number of convictions.

References

External links

2C-T - Isomer Design

The Big & Dandy 2C-T Thread - Bluelight

2C-T - PiHKAL - Erowid

2C-T - PiHKAL - Isomer Design
{{Chemical classes of psychoactive drugs 5-HT2A agonists 5-HT2B agonists 2C (psychedelics) Psychedelic phenethylamines Serotonin receptor agonists Thioethers