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2,4,5-Trimethoxyphenethylamine
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2,4,5-Trimethoxyphenethylamine
2C-O, also known as 2,4,5-trimethoxyphenethylamine (2,4,5-TMPEA) or TMPEA-2, is a serotonin receptor modulator of the phenethylamine and 2C families. It is a positional isomer of the natural entheogen mescaline (3,4,5-trimethoxyphenethylamine) and is the α-desmethyl analogue of 2,4,5-trimethoxyamphetamine (TMA-2). The drug is the parent compound of the 2C-O series of drugs. 2C-O appears to be inactive in terms of psychoactive effects in humans, at least at doses that have been assessed. In any case, it is a low-potency full agonist of the serotonin 5-HT2 receptors in vitro, including of the serotonin 5-HT2A receptor. 2C-O was first described by Max Jansen in 1931 and was further described by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).
2C-O at a dose of under 300 mg by injection was reported to produce similar psychedelic effects as mescaline by Max Jansen in 1931, albeit with more nausea and no euphoria. Conversely, in a subsequent report described by Alexander Shulgin, it was said to be indistinguishable from placebo at a dose of up to 300 mg orally. The drug was also combined with the monoamine oxidase inhibitor (MAOI) harmaline, which acts as a reversible inhibitor of monoamine oxidase A (RIMA). Even with a dose of 150 mg harmaline and 200 mg 2C-O orally however, there were no additional hallucinogenic effects that could not be explained by harmaline alone.
According to Shulgin, the present-day consensus is that 2C-O by itself is inactive. In PiHKAL (Phenethylamines I Have Known and Loved), its dose is listed as greater than 300 mg orally and its duration as unknown. Although 2C-O does not seem to produce effects by itself, the drug at a dose of 200 mg orally was reported to strongly potentiate the action of 100 mg mescaline when employed as pretreatment 45 minutes prior to the administration of mescaline.
The apparent inactivity of 2C-O (2,4,5-trimethoxyphenethylamine) in humans has been described as enigmatic because 2C-O's amphetamine (α-methyl) counterpart 2,4,5-trimethoxyamphetamine (TMA-2) is active, and because the drug's positional isomer mescaline (3,4,5-trimethoxyphenethylamine) is also active.
2C-O has been found to act as full agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. However, it showed more than two orders of magnitude lower potency in activating the serotonin 5-HT2A receptor than 2C-B and 2C-I. On the other hand, 2C-O was similar in potency to mescaline as a serotonin 5-HT2A receptor agonist, with EC50 values of 195 nM and 646 nM in terms of Gq signaling, respectively. The drug also showed higher efficacy than mescaline as a serotonin 5-HT2A receptor agonist (Emax = 96–100% vs. 33–74%, respectively).
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. 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. These findings suggest that 2C-O may be less susceptible to metabolism by monoamine oxidase (MAO) than mescaline. Moreover, it is now known that 2C-O shows far lower potency as a serotonin 5-HT2A receptor agonist than other 2C drugs.
Although 2C-O and certain derivatives such as 2C-O-4 appear to be inactive or of 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.
2C-O, also known as 2,4,5-trimethoxyphenethylamine (2,4,5-TMPEA), is a substituted phenethylamine and 2C derivative.
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2,4,5-Trimethoxyphenethylamine
2C-O, also known as 2,4,5-trimethoxyphenethylamine (2,4,5-TMPEA) or TMPEA-2, is a serotonin receptor modulator of the phenethylamine and 2C families. It is a positional isomer of the natural entheogen mescaline (3,4,5-trimethoxyphenethylamine) and is the α-desmethyl analogue of 2,4,5-trimethoxyamphetamine (TMA-2). The drug is the parent compound of the 2C-O series of drugs. 2C-O appears to be inactive in terms of psychoactive effects in humans, at least at doses that have been assessed. In any case, it is a low-potency full agonist of the serotonin 5-HT2 receptors in vitro, including of the serotonin 5-HT2A receptor. 2C-O was first described by Max Jansen in 1931 and was further described by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).
2C-O at a dose of under 300 mg by injection was reported to produce similar psychedelic effects as mescaline by Max Jansen in 1931, albeit with more nausea and no euphoria. Conversely, in a subsequent report described by Alexander Shulgin, it was said to be indistinguishable from placebo at a dose of up to 300 mg orally. The drug was also combined with the monoamine oxidase inhibitor (MAOI) harmaline, which acts as a reversible inhibitor of monoamine oxidase A (RIMA). Even with a dose of 150 mg harmaline and 200 mg 2C-O orally however, there were no additional hallucinogenic effects that could not be explained by harmaline alone.
According to Shulgin, the present-day consensus is that 2C-O by itself is inactive. In PiHKAL (Phenethylamines I Have Known and Loved), its dose is listed as greater than 300 mg orally and its duration as unknown. Although 2C-O does not seem to produce effects by itself, the drug at a dose of 200 mg orally was reported to strongly potentiate the action of 100 mg mescaline when employed as pretreatment 45 minutes prior to the administration of mescaline.
The apparent inactivity of 2C-O (2,4,5-trimethoxyphenethylamine) in humans has been described as enigmatic because 2C-O's amphetamine (α-methyl) counterpart 2,4,5-trimethoxyamphetamine (TMA-2) is active, and because the drug's positional isomer mescaline (3,4,5-trimethoxyphenethylamine) is also active.
2C-O has been found to act as full agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. However, it showed more than two orders of magnitude lower potency in activating the serotonin 5-HT2A receptor than 2C-B and 2C-I. On the other hand, 2C-O was similar in potency to mescaline as a serotonin 5-HT2A receptor agonist, with EC50 values of 195 nM and 646 nM in terms of Gq signaling, respectively. The drug also showed higher efficacy than mescaline as a serotonin 5-HT2A receptor agonist (Emax = 96–100% vs. 33–74%, respectively).
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. 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. These findings suggest that 2C-O may be less susceptible to metabolism by monoamine oxidase (MAO) than mescaline. Moreover, it is now known that 2C-O shows far lower potency as a serotonin 5-HT2A receptor agonist than other 2C drugs.
Although 2C-O and certain derivatives such as 2C-O-4 appear to be inactive or of 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.
2C-O, also known as 2,4,5-trimethoxyphenethylamine (2,4,5-TMPEA), is a substituted phenethylamine and 2C derivative.
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