2C-E

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| _other_data=2-(4-ethyl-2,5-dimethoxyphenyl)ethan-1-amine

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2C-E is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin[1] 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.[2]

Use and dosage

Shulgin gives the dose range of 2C-E as 10 to 25Template:Nbspmg.[1] 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.[1]

Effects

According to Shulgin, the duration of 2C-E's effects is 8 to 12Template:Nbsphours.[1]

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 +++[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."

Side effects

Adverse effects include tachycardia, hypertension, agitation, delirium, and hallucinations.[3] At least two deaths have been attributed to a 2C-E overdose.[3][4][5]

Interactions

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2C-E is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.[6][7] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-E.[6][7][8] This may result in overdose and serious toxicity.[8][6]

Pharmacology

Pharmacodynamics

2C-E activities
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 ND
5-HT2A 4.5–43.9 (Ki)
2.5–84 (EC50)
40–87% (Emax)
5-HT2B 25.1 (Ki)
190 (EC50)
66% (Emax)
5-HT2C 5.4–104 (Ki)
0.23–18.0 (EC50)
98–106% (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A >10,000
5-HT6 2,971
5-HT7 426
α1A 7,400–>10,000
α1B >10,000
α1D ND
α2A 100–490
α2B 306
α2C 90.2
β1 >10,000
β2 ND
β3 ND
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 ND
σ2 >10,000
Template:Abbrlink 1,200 (Ki) (mouse)
66–70 (Ki) (rat)
1,100 (EC50) (mouse)
180 (EC50) (rat)
6,410–>10,000 (EC50) (human)
64% (Emax) (mouse)
72% (Emax) (rat)
Template:Abbrlink >10,000 (Ki)
62,000–72,000 (Template:Abbrlink)
>100,000 (EC50)
Template:Abbrlink >10,000 (Ki)
26,000–89,000 (IC50)
>100,000 (EC50)
Template:Abbrlink >10,000 (Ki)
275,000 (IC50)
>100,000 (EC50)
Template:Abbrlink ND (IC50)
Template:Abbrlink 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: [9][10][11][12][13][14][15][16][17]

2C-E acts as a serotonin 5-HT2 receptor agonist.[11][12] Activation of the serotonin 5-HT2A receptor is thought to be responsible for its psychedelic effects.Script error: No such module "Unsubst".

It is inactive as a monoamine releasing agent and has negligible activity as a monoamine reuptake inhibitor.[13][14][12][11]

Chemistry

Properties

File:MSpectro2C-E.gif
Mass spectrometer analysis: 2C-E.

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.[18]

Society and culture

Legal status

File:Ethylphenethylamine.jpg
20 mg capsules of 2C-E.
File:2,5-dimethoxy-4-ethyl.jpg
2C-E pile.

Australia

In Queensland, 2C-E was added to the 'Dangerous Drugs' list of the 'Drugs Misuse Act 1986'[19] by the 'Drugs Misuse Amendment Act 2008'.[20] Making it illegal to produce, supply or possess.

Canada

As of October 31, 2016, 2C-E is a controlled substance (Schedule III) in Canada.[21]

China

As of October 2015, 2C-E is a controlled substance in China.[22]

Denmark

2C-E is added to the list of Schedule B controlled substances.[23]

Finland

Scheduled in "government decree on psychoactive substances banned from the consumer market".[24]

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:CN 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.[25]

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.[26]

Notes

  1. ↑ 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."

References

Template:Reflist

External links

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  1. ↑ a b c d Template:CitePiHKAL 2C-E in PiHKAL
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  26. ↑ Script error: No such module "citation/CS1".
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