2,4,5-Trimethoxyphenethylamine

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2,4,5-Trimethoxyphenethylamine (2C-O) is a chemical in the phenethylamine family that is related to the psychedelic mescaline. It is the 2,4,5-trimethoxy isomer of phenethylamine and the α-desmethyl analogue of TMA-2, making it the parent compound of the 2C-O series.

What it is
- Also called TMPEA-2, TMPEA, and other trade names.
- A small molecule with the formula C11H17NO3 and a melting point around 187–188 °C.

How it acts (in science)
- In the lab, 2C-O can activate serotonin receptors 5-HT2A, 5-HT2B, and 5-HT2C (it is a full agonist in these tests).
- It is much less potent at 5-HT2A than some related compounds, but can reach high efficacy in vitro.
- In humans, there is little evidence that 2C-O alone produces consistent psychedelic effects. Early reports described mescaline-like effects at injections under 300 mg, but oral doses up to 300 mg were reportedly not noticeable. Adding a monoamine oxidase inhibitor (harmaline) did not reveal new psychedelic effects beyond what harmaline caused on its own.
- Some studies note that 2C-O can enhance the effects of mescaline when given before it, suggesting a potential modulatory role rather than strong effects on its own.

Metabolism and production notes
- Research suggests 2C-O may be less susceptible to MAO-based breakdown than mescaline, which could influence how it is processed in the body.
- Other 2C-O derivatives can be potent 5-HT2A agonists in the lab, and related compounds like the amphetamine analogue TMA-2 are well-known psychedelics.

History and derivatives
- First described by Max Jansen in 1931; later discussed by Alexander Shulgin in PiHKAL (1991).
- A broad family of related compounds exists (2C-O-2 through 2C-O-27, and derivatives like 2C-O-4 and 2C-O-22). The NBOMe derivative 25O-NBOMe is much more potent than 2C-O.
- TeMPEA and PeMPEA derivatives (forms with four or more methoxy groups) are also part of the family.

Legal status (varies by country)
- United States: Schedule I substance (considered an isomer of mescaline).
- United Kingdom: Class A.
- Canada: Schedule III.
(Note: laws can change; check current regulations where you are.)

Summary
2C-O is a simple, closely related cousin of mescaline. It shows activity at serotonin receptors in laboratory tests, but humans generally do not experience strong psychedelic effects from 2C-O alone at typical tested doses. It has a history in early psychedelic chemistry and has spawned a number of related compounds with varying levels of potency.