3C-E, also known as 4-ethoxy-3,5-dimethoxyamphetamine or as ñ-methylescaline (3C-escaline), is a psychedelic drug of the phenethylamine, amphetamine, and 3C families related to 3,4,5-trimethoxyamphetamine (TMA). It is the amphetamine (3C) analogue of escaline.
In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 3C-E's dose as 30 to 60mg orally and its duration as 8 to 12hours. Per other sources, it has an estimated typical dose of 45mg orally. The drug has about the same potency as escaline.
The effects of 3C-E have been described as including strong visuals, closed-eye imagery like bright colors and distinct shapes, complex fantasy, strangeness, unworldliness, and unreality, an eerie state of awareness, fluctuating erotic and anti-erotic feelings, "exquisite sensitivity", heavy body discomfort, feelings of toxicity, nausea, muscle tremors, malaise, and slight teeth clenching. Shulgin concluded that it was a fascinating compound, but that it was a little too heavy on the body for most subjects.
3C-E is a potent serotonin 5-HT<sub>2A</sub> receptor agonist and also interacts with other serotonin receptors and targets. It produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.
The chemical synthesis of 3C-E has been described.
Analogues of 3C-E include TMA, MEM, 3C-FE, 3C-DFE, and 3C-TFE, among others.
3C-E was first described in the scientific literature by Benington and colleagues in 1954. Alexander Shulgin and colleagues reported an active dose of 40mg orally based on unpublished findings in a 1978 literature review. Subsequently, Shulgin further reported the properties and effects of 3C-E in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991. The drug was encountered as a novel designer drug in Europe in 2013.
It is a controlled substance in Canada under phenethylamine blanket-ban language.