2C-T-x

Effects

Overview

2C-T-x is a subset of the 2C-x series. Alexander Shulgin has discovered over 25 2C-T-x compounds and more are currently being made by individual scientists such as Daniel Trachsel.[1][2] PW

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 in more potent and more metabolically stable and longer acting compounds.[3–6] WP

Most of the early 2C drugs were developed by Alexander Shulgin in the 1970s and 1980s and were reviewed in his 1991 book PiHKAL (Phenethylamines I Have Known And Loved). 2C-B is the most popular of the 2C drugs. The prefix "2C" comes from the fact that they are phenethylamines rather than amphetamines and have two carbon atoms in their side chain, whereas the suffix (e.g., the "–B" or "bromo" in the case of 2C–B) refers to the substituent at the 4-position.[3][5][7][8] WP

History

History

2,4,5-Trimethoxyphenethylamine (2,4,5-TMPEA; 2C-O), the 2C positional isomer of mescaline (3,4,5-trimethoxyphenethylamine), was first synthesized by Max Jansen and was reported to produce psychedelic effects similar to those of mescaline in 1931. However, subsequent studies in the 1960s and 1970s suggested that 2,4,5-TMPEA may actually be inactive as a psychedelic in animals and humans.[9][10] WP

2C-D was the first of the 2C drugs after 2C-O to be discovered. It was synthesized and studied in animals by Beng T. Ho and colleagues at the Texas Research Institute of Mental Sciences and they published their findings in 1970. Alexander Shulgin synthesized 2C-B and 2C-D in 1974 and discovered their psychedelic effects in self-experiments conducted in 1974 and 1975. He published his findings in the scientific literature in 1975. However, Shulgin had previously tested sub-threshold doses of 2C-D in 1964 and 1965. 2C-T was first described by Shulgin and David E. Nichols in 1976. 2C-I was first described by Shulgin and colleagues in 1977 and initial psychoactivity was reported by Shulgin in 1978. Shulgin also first synthesized 2C-E in 1977. He reviewed several of these 2C drugs in a literature review in 1979. Subsequently, numerous other 2C drugs have been synthesized and characterized. Shulgin comprehensively reviewed and described the 2C drugs in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). He coined the term "2C", this term being an acronym for the two carbon atoms between the benzene ring and the amino group of the 2C drugs and a means to distinguish them from the three-carbon DOx drugs.[3][4][5][8][9][11–23] WP

2C-D was extensively studied by Hanscarl Leuner under the names DMM-PEA and LE-25 in psychedelic-assisted psychotherapy in Germany in the 1970s and 1980s. It was also informally studied by Darrell Lemaire as a potential "smart drug" in the 1970s and 1980s. He additionally developed the TWEETIO drugs such as 2CD-5-ETO via structural modification of the 2Cs. 2C-B was legitimately marketed and sold as an over-the-counter sexual enhancer under brand names like Erox in several European countries such as Germany in the 1980s and early 1990s. It was sold in adult stores, smart shops, and some nightclubs.[7][14][23–35] WP

2C-B was first encountered as a novel designer drug in the United States in 1979. It gained popularity as a recreational drug and MDMA (ecstasy) alternative in the mid-1980s. The drug became a controlled substance in the United States in 1994 or 1995. It has been said to be the most popular of the 2C drugs in terms of recreational use. Numerous other 2C drugs besides 2C-B have also since been made controlled substances.[3][5][7][33] WP

Legal status

Canada

As of October 12, 2016, the 2C-x family of substituted phenethylamines are controlled substances (Schedule III) in Canada.[36][37] WP

Pharmacology

Actions

The 2C drugs act as agonists of the serotonin 5-HT₂ receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. They are partial agonists of the serotonin 5-HT2A receptor. Most of the 2C drugs have much lower affinity for the serotonin 5-HT1A receptor than for the serotonin 5-HT2A receptor. Most of the 2C drugs have also shown about 5- to 15-fold higher affinity for the serotonin 5-HT2A receptor over the serotonin 5-HT2C receptor and about 15- to 100-fold higher affinity for the serotonin 5-HT2A receptor over the serotonin 5-HT1A receptor. The psychedelic effects of the 2C drugs are thought to be mediated specifically by activation of the serotonin 5-HT2A receptor.[38–41][46] WP

Unlike many other phenethylamines, 2C drugs, including 2C-C, 2C-D, 2C-E, 2C-I, and 2C-T-2 among others, are inactive as monoamine releasing agents and reuptake inhibitors. Most of the 2C drugs are agonists of the rat and mouse trace amine-associated receptor 1 (TAAR1). However, most are inactive as agonists of the human TAAR1. The 2C drugs show very weak monoamine oxidase inhibition, including of monoamine oxidase A (MAO-A) and/or monoamine oxidase B (MAO-B).[38][39][41][46–49] WP⚠ A table follows this text in the source and is not copied here. Open the source to see it.

Pharmacokinetics

The 2C drugs are orally active. They are metabolized by O-demethylation and deamination. This is mediated specifically by monoamine oxidase (MAO) enzymes MAO-A and MAO-B, whereas cytochrome P450 enzymes appear to metabolize only some 2C drugs and to have only a very small role.[3][50] WP

Receptor binding · Wikipedia

2C drugs at serotonin 5-HT₁ and 5-HT₂ receptors

Every row cites [38–45]

Chemistry

Pop culture

No references added yet.

References

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