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2,4,5-Trimethoxyphenethylamine
Pharmaceutical compound From Wikipedia, the free encyclopedia
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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.[1][2][3] It is a positional isomer of mescaline (3,4,5-trimethoxyphenethylamine)[1][2][4] and is the α-desmethyl analogue of 2,4,5-trimethoxyamphetamine (TMA-2).[1][2][4] The drug is the parent compound of the 2C-O series of drugs.[5] 2C-O appears to be inactive in terms of psychoactive effects in humans.[1][6][5][7] It was first described by Jansen in 1931.[1][3]
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Use and effects
2C-O at a dose of under 300 mg was reported to produce similar psychedelic effects as mescaline by Jansen in 1931, albeit with more nausea and no euphoria.[1][3] Conversely, in a subsequent report, it was said to be indistinguishable from placebo at a dose of up to 300 mg.[1][6][5] The present-day consensus appears to be that 2C-O is inactive.[1][6][5][7] In PiHKAL, its dosage is listed as greater than 300 mg and its duration as unknown.[1] Although 2C-O does not seem to produce effects by itself, 2C-O at a dose of 200 mg was reported to strongly potentiate the action of 100 mg mescaline when employed as pretreatment 45 minutes prior to the administration of mescaline.[1]
The apparent inactivity of 2C-O (2,4,5-trimethoxyphenethylamine) has been described as enigmatic, since other 2C drugs are active, since 2C-O's amphetamine (α-methyl) counterpart 2,4,5-trimethoxyamphetamine (TMA-2) is active, and since its positional isomer mescaline (3,4,5-trimethoxyphenethylamine) is active.[4]
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Interactions
Pharmacology
Summarize
Perspective
2C-O has been found to act as full agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[8] However, it showed more than two orders of magnitude lower potency in activating the serotonin 5-HT2A receptor than 2C-B and 2C-I.[8]
It has been said in the past that it is unclear whether the apparent inactivity of 2C-O is due to strong metabolism or low affinity and/or efficacy at the serotonin 5-HT2A receptor.[6][5] However, an in-vitro study using rabbit liver tissue found that 2C-O was deaminated 25% alone and 25% with the monoamine oxidase inhibitor (MAOI) semicarbazide after 1 hour whereas mescaline was deaminated 60% alone and 0% with semicarbazide after 1 hour.[9] These findings suggest that 2C-O may be less susceptible to metabolism by monoamine oxidase (MAO) than mescaline.[9] Moreover, it is now known that 2C-O shows far lower potency as a serotonin 5-HT2A receptor agonist than other 2C drugs.[8]
Although 2C-O and certain derivatives such as 2C-O-4 appear to be inactive or of very low potency in humans, 2C-O derivatives show potent serotonin 5-HT2A receptor agonism in vitro, and the amphetamine (α-methyl) analogue TMA-2, as well as derivatives like MEM, are potent psychedelics in humans.[5][1][7]
Chemistry
2C-O is a member of a class of chemical compounds commonly known as phenethylamines. Its full chemical name is 2-(2,4,5-trimethoxyphenyl)ethanamine; it is also known as 2,4,5-trimethoxyphenethylamine and 2,4,5-TMPEA.
Derivatives
A variety of derivatives of 2C-O, named 2C-O-2 (4-ethoxy-2,5-dimethoxyphenethylamine) through 2C-O-27, have been developed and studied.[5] One particularly notable derivative is 2C-O-4 (4-isopropoxy-2,5-dimethoxyphenethylamine).[5]
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History
2C-O was first described by Jansen in 1931 and was reported by him to produce psychedelic effects similar to those of mescaline.[10][3] However, subsequent tests in the 1960s and 1970s suggested that 2C-O is actually inactive as a psychedelic in animals and humans.[10][1]
Society and culture
Legal status
Canada
As of October 31, 2016, 2C-O is a controlled substance (Schedule III) in Canada.[11]
United States
2C-O is a Schedule I substance, as a positional isomer of mescaline.
United Kingdom
2C-O and all other compounds featured in PiHKAL are Class A drugs in the United Kingdom.
See also
References
External links
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