2C-E

2C-E (2,5-dimethoxy-4-ethylphenethylamine) is a psychedelic and phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin. 2C-E is commonly known as "Europa" and is typically found as a white crystalline powder.

It is commonly active in the 10–20 mg range, taken orally, and highly dose-sensitive. Insufflating (administering the chemical nasally) requires a much lower dose, typically not exceeding 5 mg, but this method of consumption elicits a noticeably painful or uncomfortable sensation in the nasal cavity for 10 minutes or so. Shulgin classified 2C-E as a member of the "magical half-dozen" in his book PiHKAL (Phenethylamines I Have Known And Loved). Many have reported that the general effects of 2C-E are similar to those of the other psychedelic phenethylamines, but far more intense. Vivid hallucinations similar to those experienced while under the influence of LSD are common, and many reports indicate that the effects of this particular chemical may be overly intense for those not well experienced with psychedelics.

Properties
2,5-Dimethoxy-4-ethylphenethylamine is a colorless oil. Crystalline forms are obtained as the amine salt by reacting the free base with a mineral acid, typically HCl.

Shulgin does not report an exact boiling point for the free base, stating only that during one synthesis the fraction boiling between 90-100 °C at 0.25 mmHg pressure was collected and converted to the hydrochloride salt. The Material Safety Data Sheet for a commercial sample of 2,5-dimethoxy-4-ethylphenethylamine hydrochloride reported the melting point as 247-249 °C.

Effects
The total duration of 2C-E's effects is generally between six and ten hours for an average dose, with the plateau lasting between three and six hours. For such a dose, the onset of effects takes approximately twenty to ninety minutes and perception may be somewhat altered for up to a day after ingestion. In extreme cases where between seventy-five and one hundred milligrams of 2C-E were ingested, the duration of effects has exceeded twenty-four hours, with plateaus exceeding ten hours in length and an onset of effects within the first five minutes after the ingestion of the drug. The concurrent use of SSRIs generally has a palliative effect upon both the intensity and duration of the effects of 2C-E during their plateau stage. 2C-E is also thought to overpower certain other drugs, though research is very minimal, mostly coming from PiHKAL (Alexander and Ann Shulgin's research), assumptions or comparison with the well researched and very closely related 2C-B, and the subjective effects that its users have experienced.

Compared to similar compounds such as 2C-I and 2C-B, 2C-E is more likely to produce strong synesthesia, sound distortion and an enhancement of the experience of music, and, most notably, visuals. While many users of lower doses of 2C-E have reported that the compound produces mainly closed-eye visuals, users of higher doses have compared its open-eye visuals with those produced by LSD; a significant proportion of these comparisons have favored the visual effects of 2C-E in terms both of their geometric complexity and in the variety of colors seen during an experience. The euphoriant effect shared by several other psychedelic phenethylamines seems only to have been reported relatively rarely by users of 2C-E; the compound has been described it as "difficult" by its users, including its inventor Shulgin:
 * "Let it (2C-E) rest as being a difficult and worthwhile material."

At doses approximating or exceeding twenty to twenty-five milligrams, 2C-E can produce intensely colorful, highly complex, moving, fractal-like patterning, Persian carpet-type visuals, three-dimensional visual effects, and, sometimes, visual patterning strongly resembling biological structures, such as vines, tentacles, and even eyeballs. The visual distortions produced by 2C-E are comparable in some respects to those produced by mescaline, and some users of both drugs have reported that the visual effects of 2C-E are more emphatic of color than are mescaline's corresponding effects, while mescaline's visuals are more emphatic of geometric structure.

2C-E also seems to make some users more likely to confront personal issues than LSD, and comparisons are often made between the two. However, 2C-E's chemical structure is fairly different from that of LSD, and while the both are serotonin agonists, 2C-E's body load is a highly unusual one. Several users have described it, roughly, as a "profound feeling of general discomfort". It is sometimes characterized by urges to shift the position of one's body, strong nausea at high doses leading often to vomiting, itching, prolonged tensing of unusual combinations of muscle groups which can occur without the user's knowledge over a long period of time, diarrhea, and an accompanying feeling of "disconnection from one's digestive tract". Other users report little or no body load on 2C-E, and experience instead a strong euphoria.

2C-E's distortion of sounds is also quite profound, and includes the flanging of sounds, echoing, pitch shifting, and the perceived synthesis of new sounds not derived from one's immediate environment, such as scraping, drilling, and popping. Again, many of the more unusual distortions of sound are only experienced after the ingestion (or, rarely, insufflation) of a higher dose. Insufflation greatly increases the potency of the drug, and should be used with even more caution ( The related compound 2-C-T-7 has caused death at 20–35 mg insufflated, a strong dose, but there are reports of 120 mg IV doses of 2C-E)

2C-E can also produce distortions in the user's perception of the passage of time leading to an illusion of moderate to extreme time dilation

2C-E's effects are often described as "neutral", in comparison with other psychedelic chemicals and even other [2C-x] related molecules. In PiHKAL, Shulgin states:
 * "Here is another of the magical half-dozen. The range is purposefully broad. At 10 milligrams there have been some pretty rich +++ experiences, and yet I have had the report from one young lady of a 30 milligram trial that was very frightening. My first experience with 2C-E was really profound, and it is the substance of a chapter within the story. Several people have said, about 2C-E, "I don't think I like it, since it isn't that much fun. But I intend to explore it again." There is something here that will reward the experimenter. 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."

Alexander Shulgin, who first synthesized the 2C-X chemicals, created a list of the "magical half dozen" of phenethylamines which felt were the most "magical" or useful. The list includes 2C-E, 2C-B, 2C-T-7, 2C-T-2, DOM, and Mescaline.

Like all psychedelics, 2C-E produces a very altered state of consciousness. One unusual side of 2C-E's effects is that some users have reported experiencing "relatively normal thought processes" even while experiencing visual and auditory distortions. These users suggest, in other words, that 2C-E doesn't impair judgment as deeply as do many other psychedelics with otherwise-similar effects; however, these claims have not been tested in any controlled study.

The wide difference between different users' accounts of the intensity, duration, and nature of the effects of 2C-E can be largely attributed to users' highly varying dosage of the drug. Resources like Erowid suggest that an average dose of 2C-E might be between ten and fifteen milligrams, and Erowid gives the highest "heavy" dose as twenty-five milligrams. Elsewhere on the Internet, and especially in various forums for users of psychedelics, users have reported taking up to between seventy-five and one hundred milligrams of 2C-E, and the ensuing experiences have invariably been extremely intense and very long (in some cases upwards of twenty-four hours in duration). However, no experienced user of 2C-E has recommended doses this large for any newcomer; an appropriate starting dose might be between seven and twenty milligrams for someone intending to consume 2C-E recreationally, depending on how experienced the new user is with similar drugs. Little is known about the long-term effects of its use. Importantly, 2C-E is an extremely uncommon substance with a very short history of human use, and it is possible that lasting negative effects could be produced by any dose.

Adverse Effects
It is thought that 2C-E binds to the 5-HT2A receptor, causing its visual, and intoxicating effects. Frequent high doses have been reported to cause HPPD. HPPD is a condition where after the ingestion of a psychedelic substance, the visual effects of the substance are still visible after the effects of the drug have worn off. Use of psychedelics is highly likely to cause long term visual aftereffects of some nature. Users of 2C-E should be warned that it has some of the dangerous effects of MAOIs and it should never be mixed with other substances.

Law
2C-E is unscheduled in the United States, but it is a potential analog of 2C-B, 2C-T-7 and mescaline (all three of which are scheduled substances), and as such sale for human consumption or possession to ingest or use for illicit non-medical or industrial intents and purposes could be prosecuted as crimes under the Federal Analog Act. Some states however are beginning to adopt state scheduling of the compound. 2C-E, in addition to a number of other psychedelic phenethylamines, is explicitly scheduled as Schedule I in Pennsylvania.

Denmark added 2C-E, 2C-P, DOC, and DOI to the list of Schedule I controlled substances as of April 8, 2007.

New Zealand has a catch-all Analogues section in Schedule 3 / Class C of their drug laws that would make 2C-I, 2C-E, DOI, ephedrine, and pseudoephedrine Schedule 3 compounds in New Zealand.

In Sweden, 2C-E has been controlled since Oct 1, 2004.

In the United Kingdom, 2C-E is a Class A controlled substance. The UK has the strictest laws in the EU on designer drugs. The Misuse Of Drugs Act was amended in 2002 to include a "catch most" clause outlawing every drug, and possible future drug, from the LSD (ergoline) and ecstasy (phenethylamine) chemical families (including 2C-E). The amendment is a near verbatim quote from the books of the American biochemist Alexander Shulgin, who obtained a PhD from the University of California, Berkeley. Dr Shulgin, a former research chemist at the Dow Chemical Company, re-discovered the synthesis for MDMA in 1976 and published the syntheses for more than 170 designer drugs of his own invention.

2C-E is illegal in Poland since 08.06.2011