2C-E

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 2C-E's dose range as 10 to 25 mg orally and its duration as 8 to 12 hours.^[1][8][9][3] However, in a couple of subsequent publications, he lists its dose range as only 10 to 15 mg orally.^[8][9] Shulgin describes 2C-E as having a steep dose–response curve, such that a small increase in dose can result in an unexpectedly large increase in effects.^[1][10] While a dose of 10 mg is often experienced as rich and well-tolerated, similar in character to 2C-D and 2C-B, doses of 20 to 30 mg have been described as too much and as very frightening.^[1][10] The onset of 2C-E was not described.^[1]

The effects of 2C-E have been reported to include color enhancement, visual changes and distortions, aesthetic enhancement, fantasy, profound and immersive psychedelic experiences, introspection, insights, dramatic recall of forgotten events, and discomfort, among others.^[1][11] Several short reports of the effects of 2C-E were published in the 2C-E section in PiHKAL, but were mostly described in abstract or experiential terms.^[1] However, a couple of in-depth long-form reports were also included in the first half of the book.^[1]

According to Shulgin, 2C-E is "without any question, a complete psychedelic".^[1] He also wrote the following of the drug: "Someday, the full character of 2C-E will be understood, but for the moment, let it rest as being a difficult and worth-while material. A very much worth-while material."^[1] In other publications, Shulgin described 2C-E as an "extraordinarily powerful and effective compound" and said that it is "a most extraordinary drug, evoking for many subjects a dramatic recall of forgotten events, with a remarkable ability to interpret and analyze them. The alteration of one's state of consciousness is dramatic, often quite frightening, and yet consistently allowing a complete recall."^[8][9] Along with a few other 2Cs like 2C-B, 2C-T-2, and 2C-T-7, 2C-E is listed in PiHKAL as one of Shulgin's "magical half-dozen".^[1]

Subsequent to Shulgin's descriptions, the effects of 2C-E have been formally clinically studied.^[2] Its effects included altered perceptions, hallucinations, and euphoria, among others.^[2] The onset was within 2 hours and its duration was more than 6 hours, though these parameters were not precisely measured.^[2]

Adverse effects of 2C-E include tachycardia, hypertension, agitation, delirium, and hallucinations.^[12] At least two deaths have been attributed to a 2C-E overdose.^[12][13][14]

2C-E is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.^[3][15] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-E.^[3][15][16] This may result in overdose and serious toxicity.^[16][3]

2C-E was first synthesized by Alexander Shulgin in 1977.^[6][7] It was first briefly mentioned in the scientific literature by Shulgin and colleagues in 1978.^[26] Then, it was described in greater detail by Shulgin in 1979.^[10] Later, the drug was described in much greater detail by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.^[1]

• 2C (psychedelics)