2C-E

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IUPACName = 1-(2,5-Dimethoxy-4-ethylphenyl)-2-aminoethane
OtherNames = 2,5-Dimethoxy-4-ethyl-phenethylamine
Section1 = Chembox Identifiers
CASNo = 71539-34-9
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ChemSpiderID = 21106222
SMILES = NCCC1=C(OC)C=C(CC)C(OC)=C1
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Formula = C₁₂H₁₉NO₂
MolarMass = 209.29 gm/mol
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2C-E (2,5-dimethoxy-4-ethylphenethylamine) is a psychedelic drug and phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. Currently it is a research chemical used in scientific testing.

It is commonly active in the 10-20 mg range, taken orally, and highly dose-sensitive. Insufflating (ie administering the chemical nasally) requires a much lower dose, typically not exceeding 5mgs. 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 would indicate that the effects of this particular chemical may be overly intense for those not well experienced with psychedelics. [CitePiHKAL]

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.

Shulgin also does not report a melting point for the hydrochloride salt. The melting point of 184-185 °C previously reported in this article is incorrect. The 184-185 °C melt point value refers to the melting point of the hydrochloride salt of 5-ethoxy-4-ethyl-2-methoxyphenethylamine (2CE-5ETO in Shulgin's nomenclature).

The Material Safety Data Sheet for a commercial sample of 2,5-dimethoxy-4-ethylphenethylamine hydrochloride reported the melting point as 247-249 °C. In the absence of a published melting point for a verified sample, the melting point is currently reported in this article as unknown.

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. A few users of very high doses have reported "never feeling the same again" after having used this 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.

As compared to similar compounds such as 2C-I and 2C-B, 2C-E is more likely to produce strong synaesthesia, sound distortion and an enhancement of the experience of music, and, most notably, visuals. Some users have also reported having mystical and ego death experiences while under the influence of 2C-E. While many users of lower doses of 2C-E have reported that it 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; it has been described it as "difficult" by people who use it, including its inventor, Shulgin::"I really don't know how to put into words, or how to describe what it did and how it acted in my mind. There were parts of it that reminded me of the other phenethylamines I've tried in one way or another, but the effects of this material are really difficult to express or generalize. I think Shulgin said it best when he commented in PiHKAL, 'Let it (2C-E) rest as being a difficult and worthwhile material.' I couldn't have said it any better myself." [http://www.erowid.org/experiences/exp.php?ID=24403]

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'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". Some users report little or no body load on 2C-E, and describe in its stead 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.

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.

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 largely be accounted for by users' highly varying dosage of the drug. Sites like [http://www.erowid.com erowid] suggest that an average dose of 2C-E might be between ten and fifteen milligrams, and 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) Fact|date=February 2007. There have been no reported deaths from 2C-E use, so even these doses can be considered relatively safe considering how little is known about the long-term effects of the use of this substance. 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. 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 (analogous to the use of alcohol). Based on the current body of evidence and a comparison with the long-term effects of its close chemical analogue, mescaline, it seems reasonable to assume that 2C-E is not likely to produce such effects.

Law

2C-E is unscheduled in the United States; however, there are currently several cases pending in U.S. federal court against online vendors for selling research chemicals. These cases may address the question of whether this chemical could be legally defined as an analog of a scheduled substance. It is possible that it could be considered an analog of 2C-B or mescaline, in which case sale for human consumption or possession with the intent to ingest could be prosecuted as crimes under the Federal Analog Act.

Denmark added 2C-E, 2C-P, DOC, and DOI to the list of Schedule I controlled substances as of April 8, 2007.Fact|date=December 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, DOB, ephedrine, and pseudoephedrine Schedule 3 compounds in New Zealand.

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

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 virtual cut-and-paste from the books of the respected 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.

References

External links

* [http://www.mdma.net/uk/2005.html Project WebTryp, includes description of UK laws regarding Phenethylamines]
* [http://www.erowid.org/chemicals/2ce/ Erowid 2C-E vault]
* [http://www.erowid.org/library/books_online/pihkal/pihkal024.shtml 2C-E Entry in PiHKAL]
* [http://www.maps.org/t2e/c6.html Chapter in Myron J. Stolaroff's "Thanatos To Eros, 35 Years of Psychedelic Exploration" discussing author's experiments with 2C-E]