2C-E
Pharmaceutical compound
From Wikipedia, the free encyclopedia
2C-E, also known as 4-ethyl-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.[1][3] It is taken orally.[1][3]
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| Other names | 4-Ethyl-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-ethylphenethylamine; 2C-DOET; 2C-DOEt; Aquarust |
| Routes of administration | Oral[1] |
| Drug class | Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen |
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| Pharmacokinetic data | |
| Onset of action | <2 hours[2] |
| Duration of action | 8â12 hours[1][3][2] |
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| ECHA InfoCard | 100.221.016 |
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| Formula | C12H19NO2 |
| Molar mass | 209.289 g·molâ1 |
| 3D model (JSmol) | |
| Solubility in water | >70 mg/mL (20 °C) |
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2C-E was first synthesized by Alexander Shulgin in 1977[4][5] and was documented in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1]
Use and effects
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][3] He describes 2C-E as having a steep doseâresponse curve, such that a small increase in dose can result in an unexpectedly large increase in effects.[1] While a dose of 10 mg is often experienced as rich and well-tolerated, doses of 25 to 30 mg have been described as too much and as very frightening.[1] The onset of 2C-E was not described.[1]
2C-E's effects are often described as "neutral", in comparison with other psychedelics and even other 2C drugs.[citation needed] In PiHKAL, Shulgin states:[1]
- "Here is another of the magical half-dozen. The range is purposefully broad. At 10 milligrams there have been some pretty rich +++[nb 1] 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."
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, although these parameters were not precisely measured.[2]
Side effects
Adverse effects of 2C-E include tachycardia, hypertension, agitation, delirium, and hallucinations.[6] At least two deaths have been attributed to a 2C-E overdose.[6][7][8]
Interactions
2C-E is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.[3][9] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-E.[3][9][10] This may result in overdose and serious toxicity.[10][3]
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 307â1,190 (Ki) >10,000 (EC50) <20% (Emax) |
| 5-HT1B | 253 |
| 5-HT1D | 73.2 |
| 5-HT1E | 626 |
| 5-HT1F | ND |
| 5-HT2A | 4.5â43.9 (Ki) 2.5â84 (EC50) 40â87% (Emax) |
| 5-HT2B | 25.1 (Ki) 190 (EC50) 66% (Emax) |
| 5-HT2C | 5.4â104 (Ki) 0.23â18.0 (EC50) 98â106% (Emax) |
| 5-HT3 | >10,000 |
| 5-HT4 | ND |
| 5-HT5A | >10,000 |
| 5-HT6 | 2,971 |
| 5-HT7 | 426 |
| α1A | 7,400â>10,000 |
| α1B | >10,000 |
| α1D | ND |
| α2A | 100â490 |
| α2B | 306 |
| α2C | 90.2 |
| β1 | >10,000 |
| β2 | ND |
| β3 | ND |
| D1 | >10,000 |
| D2 | 3,200â3,339 |
| D3 | 1,345â19,000 |
| D4 | >10,000 |
| D5 | >10,000 |
| H1âH4 | >10,000 |
| M1 | >10,000 |
| M2 | >10,000 |
| M3 | 2,557 |
| M4 | >10,000 |
| M5 | 1,725 |
| I1 | >10,000 |
| Ï1 | ND |
| Ï2 | >10,000 |
| TAAR1 | 1,200 (Ki) (mouse) 66â70 (Ki) (rat) 1,100 (EC50) (mouse) 180 (EC50) (rat) 6,410â>10,000 (EC50) (human) 64% (Emax) (mouse) 72% (Emax) (rat) |
| SERT | >10,000 (Ki) 62,000â72,000 (IC50) >100,000 (EC50) |
| NET | >10,000 (Ki) 26,000â89,000 (IC50) >100,000 (EC50) |
| DAT | >10,000 (Ki) 275,000 (IC50) >100,000 (EC50) |
| MAO-A | ND (IC50) |
| MAO-B | 124,000 (IC50) |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [11][12][13][14][15][16][17][18][19] | |
2C-E acts as a serotonin 5-HT2 receptor agonist.[13][14] Activation of the serotonin 5-HT2A receptor is thought to be responsible for its psychedelic effects.[citation needed]
It is inactive as a monoamine releasing agent and has negligible activity as a monoamine reuptake inhibitor.[15][16][14][13]
Chemistry
Properties
2C-E is a colorless oil. Crystalline forms are obtained as the amine salt by reacting the free base with a mineral acid, typically hydrochloric acid (HCl).
Shulgin does not report an exact boiling point for the free base, stating only that during one synthesis the fraction boiling between 90 and 100 °C at 0.25 mmHg pressure was collected and converted to the hydrochloride salt. Shulgin reports the melting point of the hydrochloride salt as 208.5â210.5 °C.[20]
Synthesis
The chemical synthesis of 2C-E has been described.[1][20]
Analogues
Analogues of 2C-E include 2C-H (2,5-DMPEA), 2C-D, 2C-P, DOM, DOET, 2C-E-FLY, and 25E-NBOMe, among others.[1][21]
History
2C-E was first synthesized by Alexander Shulgin in 1977.[4][5] It was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1]
Society and culture
Legal status
Australia
In Queensland, 2C-E was added to the 'Dangerous Drugs' list of the 'Drugs Misuse Act 1986'[22] by the 'Drugs Misuse Amendment Act 2008'.[23] Making it illegal to produce, supply or possess.
Canada
As of October 31, 2016, 2C-E is a controlled substance (Schedule III) in Canada.[24]
China
As of October 2015, 2C-E is a controlled substance in China.[25]
Denmark
2C-E is added to the list of Schedule B controlled substances.[26]
Finland
Scheduled in "government decree on psychoactive substances banned from the consumer market".[27]
Germany
2C-E is an Anlage I controlled drug.
New Zealand
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.
Portugal
Portugal has decriminalized possession of all recreational drugs in quantities no more than a ten-day supply of that substance.[citation needed] However production and distribution (buying/selling) are a criminal offense.
Sweden
Sveriges riksdags health ministry Statens folkhälsoinstitut classified 2C-E as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Oct 1, 2004, in their regulation SFS 2004:696 listed as 2,5-dimetoxi-4-etylfenetylamin (2C-E), making it illegal to sell or possess.[28]
United Kingdom
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 MDMA (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 200 phenethylamine compounds of his own invention, and 55 tryptamine compounds many of which were also his own invention. The Shulgins were motivated to release the synthesis information as a way to protect the public's access to information about psychedelic compounds, a goal Alexander Shulgin has noted many times.
United States
As of July 9, 2012, in the United States 2C-E is a Schedule I substance under the Food and Drug Administration Safety and Innovation Act of 2012, making possession, distribution and manufacture illegal.[29]
See also
Notes
- Shulgin's +/- rating scale, per PiHKAL. See References below. Quoting: "Plus Three (+++) = Not only are the chronology and the nature of a drug's action quite clear, but ignoring its action is no longer an option. The subject is totally engaged in the experience, for better or worse."