2C-E
Template:Cs1 config Template:Infobox drug
2C-E, also known as 4-ethyl-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.<ref name="PiHKAL">Template:CitePiHKAL 2C-E in PiHKAL</ref><ref name="Dean_2013">Template:Cite journal</ref> It is taken orally.<ref name="PiHKAL" /><ref name="Dean_2013" />
2C-E was first synthesized by Alexander Shulgin in 1977<ref name="Darie_2021">Template:Cite journal</ref><ref name="Shulgin_1980">Template:Cite book</ref> and was documented in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).<ref name="PiHKAL" />
Use and effects
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 2C-E's dose range as 10 to 25Template:Nbspmg orally and its duration as 8 to 12Template:Nbsphours.<ref name="PiHKAL" /><ref name="Dean_2013" /> He 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.<ref name="PiHKAL" /> While a dose of 10Template:Nbspmg is often experienced as rich and well-tolerated, doses of 25 to 30Template:Nbspmg have been described as too much and as very frightening.<ref name="PiHKAL" /> The onset of 2C-E was not described.<ref name="PiHKAL" />
2C-E's effects are often described as "neutral", in comparison with other psychedelics and even other 2C drugs.Template:Citation needed In PiHKAL, Shulgin states:<ref name="PiHKAL" />
- "Here is another of the magical half-dozen. The range is purposefully broad. At 10 milligrams there have been some pretty rich +++<ref group="nb">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."</ref> 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.<ref name="Papaseit_2020">Template:Cite journal</ref> Its effects included altered perceptions, hallucinations, and euphoria, among others.<ref name="Papaseit_2020" /> The onset was within 2Template:Nbsphours and its duration was more than 6Template:Nbsphours, although these parameters were not precisely measured.<ref name="Papaseit_2020" />
Side effects
Adverse effects of 2C-E include tachycardia, hypertension, agitation, delirium, and hallucinations.<ref name="Topeff">Template:Cite journal</ref> At least two deaths have been attributed to a 2C-E overdose.<ref name="Topeff" /><ref>Template:Cite news</ref><ref name="Sacks">Template:Cite journal</ref>
Interactions
2C-E is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.<ref name="Dean_2013">Template:Cite journal</ref><ref name="Theobald_2007">Template:Cite journal</ref> Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-E.<ref name="Dean_2013" /><ref name="Theobald_2007" /><ref name="Halman_2024">Template:Cite journal</ref> This may result in overdose and serious toxicity.<ref name="Halman_2024" /><ref name="Dean_2013" />
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 307–1,190 (Ki) >10,000 (Template:Abbrlink) <20% (Template:Abbrlink) |
| 5-HT1B | 253 |
| 5-HT1D | 73.2 |
| 5-HT1E | 626 |
| 5-HT1F | Template:Abbr |
| 5-HT2A | 4.5–43.9 (Ki) 2.5–84 (Template:Abbr) 40–87% (Template:Abbr) |
| 5-HT2B | 25.1 (Ki) 190 (Template:Abbr) 66% (Template:Abbr) |
| 5-HT2C | 5.4–104 (Ki) 0.23–18.0 (Template:Abbr) 98–106% (Template:Abbr) |
| 5-HT3 | >10,000 |
| 5-HT4 | Template:Abbr |
| 5-HT5A | >10,000 |
| 5-HT6 | 2,971 |
| 5-HT7 | 426 |
| α1A | 7,400–>10,000 |
| α1B | >10,000 |
| α1D | Template:Abbr |
| α2A | 100–490 |
| α2B | 306 |
| α2C | 90.2 |
| β1 | >10,000 |
| β2 | Template:Abbr |
| β3 | Template:Abbr |
| D1 | >10,000 |
| D2 | 3,200–3,339 |
| D3 | 1,345–19,000 |
| D4 | >10,000 |
| D5 | >10,000 |
| H1–H4 | >10,000 |
| M1 | >10,000 |
| M2 | >10,000 |
| M3 | 2,557 |
| M4 | >10,000 |
| M5 | 1,725 |
| I1 | >10,000 |
| σ1 | Template:Abbr |
| σ2 | >10,000 |
| Template:Abbrlink | 1,200 (Ki) (mouse) 66–70 (Ki) (rat) 1,100 (Template:Abbr) (mouse) 180 (Template:Abbr) (rat) 6,410–>10,000 (Template:Abbr) (human) 64% (Template:Abbr) (mouse) 72% (Template:Abbr) (rat) |
| Template:Abbrlink | >10,000 (Ki) 62,000–72,000 (Template:Abbrlink) >100,000 (Template:Abbr) |
| Template:Abbrlink | >10,000 (Ki) 26,000–89,000 (Template:Abbr) >100,000 (Template:Abbr) |
| Template:Abbrlink | >10,000 (Ki) 275,000 (Template:Abbr) >100,000 (Template:Abbr) |
| Template:Abbrlink | Template:Abbr (Template:Abbr) |
| Template:Abbrlink | 124,000 (Template:Abbr) |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: <ref name="PDSPKiDatabase">Template:Cite web</ref><ref name="BindingDB">Template:Cite web</ref><ref name="Ray_2010">Template:Cite journal</ref><ref name="Rickli_2015">Template:Cite journal</ref><ref name="Eshleman_2014">Template:Cite journal</ref><ref name="Nagai_2007">Template:Cite journal</ref><ref name="Pottie_2020">Template:Cite journal</ref><ref name="Wagmann_2019">Template:Cite journal</ref><ref name="Simmler_2016">Template:Cite journal</ref> | |
2C-E acts as a serotonin 5-HT2 receptor agonist.<ref name="Ray_2010" /><ref name="Rickli_2015" /> Activation of the serotonin 5-HT2A receptor is thought to be responsible for its psychedelic effects.Template:Citation needed
It is inactive as a monoamine releasing agent and has negligible activity as a monoamine reuptake inhibitor.<ref name="Eshleman_2014" /><ref name="Nagai_2007" /><ref name="Rickli_2015" /><ref name="Ray_2010" />
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 208.5–210.5 °C.<ref name="Shulgin_2011" />
Synthesis
The chemical synthesis of 2C-E has been described.<ref name="PiHKAL" /><ref name="Shulgin_2011">Template:Cite book</ref>
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.<ref name="PiHKAL" /><ref name="Trachsel_2013">Template:Cite book</ref>
History
2C-E was first synthesized by Alexander Shulgin in 1977.<ref name="Darie_2021" /><ref name="Shulgin_1980" /> It was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).<ref name="PiHKAL" />
Society and culture
Legal status
Australia
In Queensland, 2C-E was added to the 'Dangerous Drugs' list of the 'Drugs Misuse Act 1986'<ref>Template:Cite web</ref> by the 'Drugs Misuse Amendment Act 2008'.<ref>Template:Cite web</ref> Making it illegal to produce, supply or possess.
Canada
As of October 31, 2016, 2C-E is a controlled substance (Schedule III) in Canada.<ref>Template:Cite periodical</ref>
China
As of October 2015, 2C-E is a controlled substance in China.<ref>Template:Cite web</ref>
Denmark
2C-E is added to the list of Schedule B controlled substances.<ref>Template:Cite web</ref>
Finland
Scheduled in "government decree on psychoactive substances banned from the consumer market".<ref>Template:Cite web</ref>
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.Template: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.<ref>Template:Cite web</ref>
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.<ref name="erowid-law">Template:Cite web</ref>
See also
Notes
<references group="nb" />
References
External links
- 2C-E - Isomer Design
- 2C-E - PsychonautWiki
- 2C–E - Erowid
- 2C-E - PiHKAL - Erowid
- 2C-E - PiHKAL - Isomer Design
- The Big & Dandy 2C-E Thread - Bluelight
- 2C-E: Psychedelic Information & Safety - Tripsitter
- A Most Remarkable Material, 2C-E - Thanatos To Eros, 35 Years of Psychedelic Exploration - Myron J. Stolaroff
Template:Psychedelics Template:Serotonin receptor modulators Template:TAAR modulators Template:Phenethylamines