2C-E

2C-E (4-ethyl-2,5-dimethoxyphenethylamine) is a psychedelic phenethylamine first described by chemist Alexander Shulgin in his book PiHKAL: A Chemical Love Story. 2C-E is usually taken orally or insufflated with a typical dose in the range of 5-15mg. 2C-E has both hallucinogenic and entactogenic properties, and is often described as being more intense and more visual than other phenethylamines, and lasting a much longer period of time, about 10-12 hours. In March and May of 2011, 2C-E attracted much media coverage when it was suspected to have caused the deaths of several people; since this time it was been suggested that the deaths were due to Bromo-DragonFLY and not 2C-E.

Introduction to 2C-E

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2C-E (2,5-dimethoxy-4-ethylphenethylamine), part of a series of analogues informally referred to as the '2Cs', is a methoxylated phenethylamine derivative. It is distinguishable from other members of the '2C' series due to an ethyl group para to the ethylamine chain.

Using 2C-E

2C-E Dose and Bodyload

Ways of administration

Oral, sublingual, insufflation, rectal, intravenous

Sublingual 2C-E? Alternative routes for harnessing a difficult substance
Insufflation of 2C-E
Injecting 2C-E



Effects of 2C-E

2C-E is one of the more potent and longer lasting analogs of the 2C chemical family. It is often described as being the more visual and colorful of the compounds, producing closed eye visuals and open eye visuals at lower doses than similar counterparts like 2C-I and 2C-T-2. At lower doses the closed eye visual effects can be characterized as entopic hallucinations (phosphenes); seeing repetitions of geometric patterns like honeycombs or spider webs. 2C-E is known to be produce more colorful visual effects than the other 2C's. Synesthesia can occur, where the user experiences one sensory input as intimately bound to another; ie. sounds can have a specific color. Erratic hallucinations are also common; where wiggling or waving of lines and shadows gives ordinary static objects a vibrant appearance of malleability. Patterns and textures in carpets, ceilings, window blinds, tree leaves, wood grain, and other natural or artificial objects are affected and brought to life. Flat surfaces can take on an oil, pastel or plastic saturation. Kaleidoscopic closed eye visuals are very common, along with tracers or trails behind fast moving objects.

2C-E has a very steep dose-response curve as compared to many other 2C's - a small increase in dose can evoke a significantly stronger response. Careful measurement of quantity is crucial if one is to experiment with this compound due to the fact that an additional 2mg could dramatically alter the experience. It has been described as "not that much fun", possibly because it has the capacity to bring forth emotions and thoughts that may be uncomfortable for the user to asses under a discerning eye. 2C-T-2 and 2C-T-7 are also known to alter cognitive processes in a similar way, calling forth an introspective view. These compounds are likely more appropriate in a more solitary setting, or with close friends. There can occur moments of insight and mental clarity while others can find otherwise simple tasks confusing and difficult. Emotions and feelings can be significantly modulated by sensory input (ie. music) and surroundings or activities. The length of the 2C-E trip can also make the trip exhausting, long and drawn out, potentially lasting 8-12 hours as opposed to 2C-I, which commonly lasts 6-10 hours (but usually closer to the lower end of this range). It can take 1-2 hours or longer for the 2C-E trip to reach it's peak, depending on whether or not it is consumed on a full stomach.

It can produce nausea during the onset and rising action; vomiting can occur. This can contrasts 2C-B which is described as more blissful and pleasant in physical effects, however, with increasing potency all 2C's can cause nausea or unease. Nonetheless, many users describe rushes of euphoria with many of the 2C's during the middle and latter half of the trip, and some report no nausea at all. Users have often reported chills or a feeling of cold during the first half of the trip. The 2C's have been compared to a combination of a tryptamine with MDMA due to their tendency to cause visual hallucinations in tandem with warm rushes of euphoria, but this is only a very rough comparison. They have been classified as empathogens and entactogens to some degree. The initial come up can be somewhat lucid, "loopy", with alternating feelings of chills and warmth. There can be a sense of pressure or swelling in the torso and head. The hands and body can shake or tremble, there can occur a tightness in the jaw. The body buzz tends to resolve during the latter half of the trip, and the psychological effects can be more pronounced.

Effects list

Positive effects [1]
  • sense of well-being (enhanced lucidity, sense of inner peace)
  • mental and physical stimulation
  • increase in associative and creative thinking
  • increased awareness and appreciation of music
  • increased awareness of senses
  • increased tactile sensation
  • visual patterning, closed and open eye visuals
  • insight into personal issues
  • profound life-changing spiritual experiences

Neutral effects
  • general change in consciousness (as with most psychoactives)
  • pupil dilation
  • confusion, difficulty concentrating, and/or scrambled thoughts
  • change in perception of time
  • slight increase in body temperature
  • slight increase in heart rate

Negative effects
  • muscle tension and aching
  • jaw tension
  • increased perspiration
  • gastrointestinal discomfort, nausea and vomiting
  • dizziness, confusion
  • over-awareness & over-sensitization to music and noise
  • paranoia, fear
  • unwanted life-changing spiritual experiences
  • possible difficulty integrating experiences



Combinations with 2C-E

With mescaline experience
While on Fluoxetine
With Cannabis
With MDMA
With 2C-I


Different Uses for 2C-E



Pharmacology of 2C-E

2C-E inhibits the reuptake of monoamines, which include dopamine, norepinephrine, and serotonin - but exerts its predominant activity upon serotonin and norepinephrine. In comparison to other members of the '2C' series, Nagai et. al. observed that 2C-E is a more potent inhibitor of serotonin reuptake than 2C-I, but less potent than 2C-C. It is less potent than both 2C-I and 2C-C at inhibiting the reuptake of norepinephrine, however. In comparison to other phenethylamines, 2C-E is considerably less potent at inhibiting both serotonin and norepinephrine reuptake than MDMA, Methylone, BDB, and MBDB. It appears to be more potent than both TMA, TMA-2, and TMA-6 at inhibiting reuptake of both serotonin and norepinephrine.

Additionally, 2C-E is a slightly less potent reuptake inhibitor for serotonin, and quite a bit less potent at inhibiting reuptake of norepinephrine, than BZP - as well as less potent at inhibiting the reuptake of norepinephrine and serotonin than AMT, 5-MeO-MIPT, 5-MeO-DIPT, and 5-MeO-DMT.

When evaluated for its capacity in generating monoamine release, 2C-E (as well as 2C-I and 2C-C) were characterized by relatively low levels of activity when compared to other phenethyalmines such as methylone and MBDB.[2] However, this is not to suggest that the drugs possess no monoamine releasing properties - rather, reuptake is their predominant mode of action.

Monoamine Re-uptake into rat brain synaptosome

Below is a table taken from Nagai et. al., 2006 that includes 2C-E in comparison to other phenethylamines, tryptamines, and piperazines - as well as cocaine and methamphetamine.

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Studies of Cortical G-Protein Binding

Nonaka et. al. assessed the potency of several phenethylamines, tryptamines and piperazines by assessing GTP-binding, in concentration-dependent manners, to cortical membranes. Below is a concentration curve for [35S]GTPgS cortical binding by several drugs, including 2C-E in (A).

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The curves demonstrate that, of the tested drugs considered members of the '2C' series, 2C-E least potently activated G-proteins.

In comparing 2C-C, 2C-I, and 2C-E - the only difference in structure concerns the substituent present at the 4-position of the aromatic ring (chloride, iodide, and ethyl, respectively). Nonaka et. al. propose that, from order of potency, a steric hindrance similar to that of the 5-MeO-tryptamines exists. They cite Glennon et. al. as suggesting that behavioral activity of phenethylamine drugs depend upon the size of the substituent at the 4-position of 2,5-di-methoxyamphetamine as a parent structure; the results of the above experiment suggest that steric hindrance is crucial in the binding of compounds to serotonin receptors.

In other words, potency at serotonin receptors is likely restricted by the size of the group bound at the 4-position - in this case, an ethyl group - which is sterically larger in size than both iodide and chloride substituents, thereby explaining its low potency in comparison. Accordingly, 2C-E would also be considered lower in potency than 2C-B, though the bromide analogue was not included in the above tests.


Metabolism of 2C-E


2C-E is metabolized primarily by MAO-A and MAO-B enzymes. These are the main enzymes involved in deamination. The CYP2D6 enzyme is also involved but to a lesser extent. Due to the extensive metabolism of 2C-E by MAO-B, monoamine oxidase inhibitors (MAOI's) are contraindicated with 2C-E. [4]

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2C-E has a moderate Km value for MAO-A, and a high Km value for MAO-B. It also has a very low Vmax for MAO-A as compared to other 2C-x compounds, and a moderate Vmax for MAO-B. Both of these factors contribute to the speed of metabolism of 2C-E, which generally occurs at a slower rate compared to other popular 2C-X compounds like 2C-I and 2C-D.


Chemistry of 2C-E


Column 1 Column 2
Systematic(IUPAC) name: 2-(4-ethyl-2,5-dimethoxy)benzeneethanamine
Synonyms: 4-ethyl-2,5-dimethoxyphenethylamine, 2C-E
Molecular Formula: C12H19NO2, C12H19NO2.HCl (hydrochloride)
Molar mass: 209.28 g/mol, 245.75 g/mol (hydrochloride)[1]
CAS Registry Number: 71539-34-9
Melting Point: 210.0 °C (hydrochloride)[5]
Boiling Point: no data
Flash Point: no data
Solubility: no data
Additionnal data: none
Notes: Hydrochloride aspect: white powder[5]
2C-E is soluble in alcohol, it will go into solution in water.

See: 2C-E Solubility and Solubility of 2C-E & 2c-i

Reagent test results of 2C-E


Reagent color produced picture video
Marquis No reaction link (reference); link (results) -
Mandelin Yellow/green link (reference); link (results) -
Mecke Biege link (reference); link (results) -



The dangers of 2C-E

Since Alexander Shulgin synthesized 2C-E and described it in his book PiHKLA, 2C-E has gained popularity and been used for decades by drug users around the world. Until recently there have been no reports of a fatal overdose due to 2C-E alone.

On March 17th[6], it was reported that a 19-year-old man had died from a heart attack and two others were in critical condition after having ingested 2C-E. A total of 11 people were taken to the hospital who were in severe medial distress. Media reports describe it as 'similar to Ecstasy'. About one month later on May 7th[7], it was reported that an emergency call to a Konawa residence occured. Around 8 people were suffering from "severe drug toxicity", and were taken to the hospital. One of these people died in Seminole hospital and 2 were reported in critical condition.The drug said to have been taken was 2C-E.

Since these incidences, chemical analysis have led to believe that the actual drug taken was not 2C-E, but rather Bromo-DragonFLY, a psychedelic and stimulant drug approximately 10 to 100 times more potent than 2C-E. In 2009, a similar case occurred where Bromo-DragonFLY was accidentally mislabeled and sold as 2C-B-FLY, which also resulted in the deaths of several people.

These are the dangers common to all psychedelic drugs:

Accidental injury.
When on a psychedelic drug, it is easier to accidentally injure yourself. Also because of the disorientating and potentially delusion inspiring nature of the experience, you could be lead to inflict harm on others or yourself. People have fallen off rooftops, run into traffic, attempted to throw people off rooftops as 'sacrifices', drowned, and so on. The best way of protecting against this is to have a friend with you who is sober to look after you and handle any negative situation that might arise.

Bad trips. A bad trip is a negative psychedelic experience. It can range from a mildly negative feeling of anxiety/discomfort, to full-blown psychosis. Bad trips usually ruin a psychedelic experience for the tripper and everyone else. Most bad trips are manageable, just very uncomfortable and difficult. Some are extreme and unmanageable though. It's not uncommon for a bad trip to result in lingering psychological issues. Usually just a few days of negative emotions and anxiety. Sometimes, however, a week or so of serious anxiety, destabilized mental state and impaired functioning is possible. On very rare occasions, a month or two of severely diminished functioning, traumatized mental state, depression & crippling anxiety can occur. More information on bad trips can be found here. The best way of avoiding a bad trip is having the correct set and setting.

Permanent psychosis. Psychedelics are believed by researchers not to cause permanent psychosis, however they could trigger a latent mental illness in someone who was already predisposed to it, or make existing mental illnesses worse. If there is a history of mental illness in your family, you are more likely to be predisposed. Everyone is at some risk, however.

PTSD, anxiety disorder, depression & depersonalization. There are anecdotal reports of the trauma inflicted by some bad trips leading to depression and anxiety which while usually temporary, could potentially develop into lasting disorders. While no different to the potential of any traumatic event to cause lasting disorders, nonetheless this is a danger of psychedelic drug use.

Producing 2C-E



Forms of 2C-E

Appearance

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United Nations


USA

2C-E is not explicitly controlled at Federal level, though posession or distribution under certain circumstances may contravene the Federal Analog Act due to 2C-E's structural and functional similarity to the Schedule I controlled substance 2C-B.

EU


Denmark

Illegal since 2007-04-08

United Kingdom

2C-E is a Class A controlled substance as it is covered under the phenethylamine derivatives clause of the Misuse of Drugs Act 1971.

Sweden

Illegal since 2004-10-01

Other Countries


Israel

Illegal since december 2007

Japan

Illegal to possess or sell

New Zealand

Schedule 3 substance due analogue act

History of 2C-E


More 2C-E Sections

2C-E Experience Report Thread
2C-E Information/Basics
Bad trips on 2C-E?
Persistant After Effects

The latest 2C-E threads



References

  1. ^ a bErowid 2C-E Vault: Effects, locatedL http://www.erowid.org/chemicals/2ce/2ce_effects.shtml
  2. ^ a bNagai, Fumiko, Nonaka, Ryouichi, Satoh, Kanako, Kamimura, Hisashi, The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain, European Journal of Pharmacology (2006)
  3. ^Nonaka, Ryouichi, Nagai, Fumiko, Ogata, Akio, Satoh, Kanako, In Vitro Screening of Psychoactive Drugs by [35S]GTPgS Binding in Rat Brain Membranes
  4. ^Theobald DS, Maurer HH.
    “Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)”.
    Biochem Pharmacol. 2007 Jan 12;73(2):287-97.
  5. ^ a b2C-E monograph
  6. ^Drugs Forum post; 1 dead, 2 critical in Minneapolis area 2C-E overdose, located here:https://drugs-forum.com/forum/showthread.php?t=156977
  7. ^Drugs Forum post; 2 dead, 6 hospitalized in Oklahoma area Bromo-dragonfly mislabeled as 2C-E overdose, located here:https://drugs-forum.com/forum/showthread.php?t=159845







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