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| Clinical data | |
|---|---|
| Other names | 2,5-Dimethoxy-4-ethylphenethylamine; 4-Ethyl-2,5-dimethoxyphenethylamine; Aquarust |
| Routes of administration | Oral |
| Drug class | Serotonin5-HT2 receptoragonist;Serotonergic psychedelic;Hallucinogen |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.221.016 |
| Chemical and physical data | |
| Formula | C12H19NO2 |
| Molar mass | 209.289 g·mol−1 |
| 3D model (JSmol) | |
| Solubility in water | >70 mg/mL (20 °C) |
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2C-E is apsychedelicphenethylamine of the2C family. It was first synthesized byAlexander Shulgin[1] and documented in his bookPiHKAL. Like the other substances in its family, it produces sensory and cognitive effects in its physical reactions with living organisms.[2]
According to Shulgin, the duration of 2C-E's effects is generally between six and ten hours for an average dose, with the plateau lasting between three and six hours.[1]
2C-E's effects are often described as "neutral", in comparison with other psychedelic chemicals and even other2C-x related molecules. InPiHKAL, Shulgin states:
Adverse effects includetachycardia,hypertension,agitation,delirium, andhallucinations.[3] At least two deaths have been attributed to a 2C-E overdose.[3][4][5]
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 307–1,190 (Ki) >10,000 (EC50Tooltip half-maximal effective concentration) <20% (EmaxTooltip maximal efficacy) |
| 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 |
| TAAR1Tooltip Trace amine-associated receptor 1 | 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) |
| SERTTooltip Serotonin transporter | >10,000 (Ki) 62,000–72,000 (IC50Tooltip half-maximal inhibitory concentration) >100,000 (EC50) |
| NETTooltip Norepinephrine transporter | >10,000 (Ki) 26,000–89,000 (IC50) >100,000 (EC50) |
| DATTooltip Dopamine transporter | >10,000 (Ki) 275,000 (IC50) >100,000 (EC50) |
| MAO-ATooltip Monoamine oxidase A | ND (IC50) |
| MAO-BTooltip Monoamine oxidase 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:[6][7][8][9][10][11][12][13][14] | |
2C-E acts as aserotonin5-HT2 receptoragonist.[8][9] Activation of the serotonin5-HT2A receptor is thought to be responsible for itspsychedelic effects.[citation needed]
It is inactive as amonoamine releasing agent and has negligible activity as amonoamine reuptake inhibitor.[10][11][9][8]
2C-E ismetabolized by themonoamine oxidase (MAO)enzymesMAO-A andMAO-B.[15][16]Monoamine oxidase inhibitors (MAOIs) such asphenelzine,tranylcypromine,moclobemide, andselegiline may potentiate the effects of 2C-E.[15][16][17] This may result inoverdose and serioustoxicity.[17][15]
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, typicallyhydrochloric 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]
InQueensland, 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.
As of October 31, 2016, 2C-E is a controlled substance (Schedule III) in Canada.[21]
As of October 2015, 2C-E is a controlled substance in China.[22]
2C-E is added to the list of Schedule B controlled substances.[23]
Scheduled in "government decree on psychoactive substances banned from the consumer market".[24]
2C-E is anAnlage I controlled drug.
New Zealand has a catch-all Analogues section in Schedule 3 / Class C of their drug laws that would make2C-I, 2C-E, DOI,ephedrine, andpseudoephedrine Schedule 3 compounds in New Zealand.
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.
Sveriges riksdags health ministryStatens folkhälsoinstitut [sv] classified 2C-E as "health hazard" under the actLagen om förbud mot vissa hälsofarliga varor [sv] (translatedAct 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]
In the United Kingdom, 2C-E is a Class A controlled substance. The UK has the strictest laws in the EU ondesigner 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 biochemistAlexander 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.
As of July 9, 2012, in theUnited States 2C-E is aSchedule I substance under theFood and Drug Administration Safety and Innovation Act of 2012, making possession, distribution and manufacture illegal.[26]
