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2C-E is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin<ref name="PiHKAL">Template:CitePiHKAL 2C-E in PiHKAL</ref> and documented in his book PiHKAL. Like the other substances in its family, it produces sensory and cognitive effects in its physical reactions with living organisms.<ref>Template:Cite journal</ref>
Use and dosageEdit
Shulgin gives the dose range of 2C-E as 10 to 25Template:Nbspmg.<ref name="PiHKAL" /> 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" />
EffectsEdit
According to Shulgin, the duration of 2C-E's effects is 8 to 12Template:Nbsphours.<ref name=PiHKAL/>
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 +++<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."
Side effectsEdit
Adverse effects 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>
InteractionsEdit
2C-E is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.<ref name="DeanStellpflugBurnett2013">Template:Cite journal</ref><ref name="TheobaldMaurer2007">Template:Cite journal</ref> Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-E.<ref name="DeanStellpflugBurnett2013" /><ref name="TheobaldMaurer2007" /><ref name="HalmanKongSarris2024">Template:Cite journal</ref> This may result in overdose and serious toxicity.<ref name="HalmanKongSarris2024" /><ref name="DeanStellpflugBurnett2013" />
PharmacologyEdit
PharmacodynamicsEdit
| 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">{{#invoke:citation/CS1|citation | CitationClass=web
}}</ref><ref name="BindingDB">{{#invoke:citation/CS1|citation |
CitationClass=web
}}</ref><ref name="Ray2010">Template:Cite journal</ref><ref name="RickliLuethiReinisch2015">Template:Cite journal</ref><ref name="EshlemanForsterWolfrum2014">Template:Cite journal</ref><ref name="NagaiNonakaSatohHisashiKamimura2007">Template:Cite journal</ref><ref name="PottieCannaertStove2020">Template:Cite journal</ref><ref name="WagmannBrandtStratford2019">Template:Cite journal</ref><ref name="SimmlerBuchyChaboz2016">Template:Cite journal</ref> | |
2C-E acts as a serotonin 5-HT2 receptor agonist.<ref name="Ray2010" /><ref name="RickliLuethiReinisch2015" /> 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="EshlemanForsterWolfrum2014" /><ref name="NagaiNonakaSatohHisashiKamimura2007" /><ref name="RickliLuethiReinisch2015" /><ref name="Ray2010" />
ChemistryEdit
PropertiesEdit
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 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="shulginIndex">Template:Cite book</ref>
Society and cultureEdit
Legal statusEdit
AustraliaEdit
In Queensland, 2C-E was added to the 'Dangerous Drugs' list of the 'Drugs Misuse Act 1986'<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> by the 'Drugs Misuse Amendment Act 2008'.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Making it illegal to produce, supply or possess.
CanadaEdit
As of October 31, 2016, 2C-E is a controlled substance (Schedule III) in Canada.<ref>Template:Cite periodical</ref>
ChinaEdit
As of October 2015, 2C-E is a controlled substance in China.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
DenmarkEdit
2C-E is added to the list of Schedule B controlled substances.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
FinlandEdit
Scheduled in "government decree on psychoactive substances banned from the consumer market".<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
GermanyEdit
2C-E is an Anlage I controlled drug.
New ZealandEdit
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.
PortugalEdit
Portugal has decriminalized possession of all recreational drugs in quantities no more than a ten-day supply of that substance.Template:CN However production and distribution (buying/selling) are a criminal offense.
SwedenEdit
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>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
United KingdomEdit
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 StatesEdit
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">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
NotesEdit
<references group="nb" />
ReferencesEdit
External linksEdit
- 2C-E - Isomer Design
- 2C-E - PsychonautWiki
- Erowid 2C–E vault
- 2C-E: Psychedelic Information & Safety - Tripsitter
- Chapter in Myron J. Stolaroff's Thanatos To Eros, 35 Years of Psychedelic Exploration discussing author's experiments with 2C-E
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