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2C-E
Chemical compound

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

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Effects

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.3

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 +++4 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.5 At least two deaths have been attributed to a 2C-E overdose.678

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

2C-E is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.910 Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-E.111213 This may result in overdose and serious toxicity.1415

Pharmacology

Pharmacodynamics

2C-E activities
TargetAffinity (Ki, nM)
5-HT1A307–1,190 (Ki)>10,000 (EC50Tooltip half-maximal effective concentration)<20% (EmaxTooltip maximal efficacy)
5-HT1B253
5-HT1D73.2
5-HT1E626
5-HT1FND
5-HT2A4.5–43.9 (Ki)2.5–84 (EC50)40–87% (Emax)
5-HT2B25.1 (Ki)190 (EC50)66% (Emax)
5-HT2C5.4–104 (Ki)0.23–18.0 (EC50)98–106% (Emax)
5-HT3>10,000
5-HT4ND
5-HT5A>10,000
5-HT62,971
5-HT7426
α1A7,400–>10,000
α1B>10,000
α1DND
α2A100–490
α2B306
α2C90.2
β1>10,000
β2ND
β3ND
D1>10,000
D23,200–3,339
D31,345–19,000
D4>10,000
D5>10,000
H1–H4>10,000
M1>10,000
M2>10,000
M32,557
M4>10,000
M51,725
I1>10,000
σ1ND
σ2>10,000
TAAR1Tooltip Trace amine-associated receptor 11,200 (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 AND (IC50)
MAO-BTooltip Monoamine oxidase B124,000 (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: 161718192021222324

2C-E acts as a serotonin 5-HT2 receptor agonist.2526 Activation of the serotonin 5-HT2A receptor is thought to be responsible for its psychedelic effects.

It is inactive as a monoamine releasing agent and has negligible activity as a monoamine reuptake inhibitor.27282930

Chemistry

Properties

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.31

Society and culture

Legal status

Australia

In Queensland, 2C-E was added to the 'Dangerous Drugs' list of the 'Drugs Misuse Act 1986'32 by the 'Drugs Misuse Amendment Act 2008'.33 Making it illegal to produce, supply or possess.

Canada

As of October 31, 2016, 2C-E is a controlled substance (Schedule III) in Canada.34

China

As of October 2015, 2C-E is a controlled substance in China.35

Denmark

2C-E is added to the list of Schedule B controlled substances.36

Finland

Scheduled in "government decree on psychoactive substances banned from the consumer market".37

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. 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.38

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.39

Notes

References

  1. Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. 2C-E in PiHKAL 0-9630096-0-5 ↩

  2. Papaseit E, Olesti E, Pérez-Mañá C, Torrens M, Grifell M, Ventura M, et al. (2020). "Acute Effects of 2C-E in Humans: An Observational Study". Frontiers in Pharmacology. 11: 233. doi:10.3389/fphar.2020.00233. PMC 7093582. PMID 32256350. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7093582 ↩

  3. Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. 2C-E in PiHKAL 0-9630096-0-5 ↩

  4. 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." ↩

  5. Topeff JM, Ellsworth H, Willhite LA, Bangh SA, Edwards EM, Cole JB (2011). "A case series of symptomatic patients, including one fatality, following 2C-E exposure". Clin. Toxicol. 49: 526. ↩

  6. Topeff JM, Ellsworth H, Willhite LA, Bangh SA, Edwards EM, Cole JB (2011). "A case series of symptomatic patients, including one fatality, following 2C-E exposure". Clin. Toxicol. 49: 526. ↩

  7. Pham S (18 March 2011). "Man Arrested in Mass Drug Overdose That Killed 1 Teen and Left 10 People Hospitalized". ABC World News. Retrieved 29 June 2014. https://abcnews.go.com/US/man-arrested-minnesota-deadly-mass-drug-overdose/story?id=13166375 ↩

  8. Sacks J, Ray MJ, Williams S, Opatowsky MJ (2012). "Fatal toxic leukoencephalopathy secondary to overdose of a new psychoactive designer drug 2C-E ("Europa")". Baylor University Medical Center Proceedings. 25 (4): 374–376. doi:10.1080/08998280.2012.11928883. PMC 3448584. PMID 23077393. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3448584 ↩

  9. Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013). "2C or not 2C: phenethylamine designer drug review". J Med Toxicol. 9 (2): 172–178. doi:10.1007/s13181-013-0295-x. PMC 3657019. PMID 23494844. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3657019 ↩

  10. Theobald DS, Maurer HH (January 2007). "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)". Biochem Pharmacol. 73 (2): 287–297. doi:10.1016/j.bcp.2006.09.022. PMID 17067556. /wiki/Doi_(identifier) ↩

  11. Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013). "2C or not 2C: phenethylamine designer drug review". J Med Toxicol. 9 (2): 172–178. doi:10.1007/s13181-013-0295-x. PMC 3657019. PMID 23494844. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3657019 ↩

  12. Theobald DS, Maurer HH (January 2007). "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)". Biochem Pharmacol. 73 (2): 287–297. doi:10.1016/j.bcp.2006.09.022. PMID 17067556. /wiki/Doi_(identifier) ↩

  13. Halman A, Kong G, Sarris J, Perkins D (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". J Psychopharmacol. 38 (1): 3–18. doi:10.1177/02698811231211219. PMC 10851641. PMID 37982394. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10851641 ↩

  14. Halman A, Kong G, Sarris J, Perkins D (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". J Psychopharmacol. 38 (1): 3–18. doi:10.1177/02698811231211219. PMC 10851641. PMID 37982394. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10851641 ↩

  15. Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013). "2C or not 2C: phenethylamine designer drug review". J Med Toxicol. 9 (2): 172–178. doi:10.1007/s13181-013-0295-x. PMC 3657019. PMID 23494844. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3657019 ↩

  16. "Kᵢ Database". PDSP. 16 March 2025. Retrieved 16 March 2025. https://pdsp.unc.edu/kidb2/kidb/web/kis-results/index?KisResultsSearch%5Binput_receptors%5D=&KisResultsSearch%5Binput_sources%5D=&KisResultsSearch%5Binput_species%5D=&KisResultsSearch%5Binput_hot_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=14671&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=12943&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D= ↩

  17. Liu T. "BindingDB BDBM50240788 2-(2,5-dimethoxy-4-ethylphenyl)ethylamine::2-(4-Ethyl-2,5-dimethoxy-phenyl)-ethylamine::CHEMBL124063::US20240166618, Compound 2C-E". BindingDB. Retrieved 3 March 2025. https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50240788 ↩

  18. Ray TS (February 2010). "Psychedelics and the human receptorome". PLOS ONE. 5 (2): e9019. Bibcode:2010PLoSO...5.9019R. doi:10.1371/journal.pone.0009019. PMC 2814854. PMID 20126400. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2814854 ↩

  19. Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)" (PDF). Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099. https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf ↩

  20. Eshleman AJ, Forster MJ, Wolfrum KM, Johnson RA, Janowsky A, Gatch MB (March 2014). "Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function" (PDF). Psychopharmacology (Berl). 231 (5): 875–888. doi:10.1007/s00213-013-3303-6. PMC 3945162. PMID 24142203. https://www.researchgate.net/profile/Michael-Forster-2/publication/258061356_Behavioral_and_neurochemical_pharmacology_of_six_psychoactive_substituted_phenethylamines_Mouse_locomotion_rat_drug_discrimination_and_in_vitro_receptor_and_transporter_binding_and_function/links/53d119a00cf2f7e53cfbcd68/Behavioral-and-neurochemical-pharmacology-of-six-psychoactive-substituted-phenethylamines-Mouse-locomotion-rat-drug-discrimination-and-in-vitro-receptor-and-transporter-binding-and-function.pdf ↩

  21. Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur J Pharmacol. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101. /wiki/Doi_(identifier) ↩

  22. Pottie E, Cannaert A, Stove CP (October 2020). "In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor". Arch Toxicol. 94 (10): 3449–3460. Bibcode:2020ArTox..94.3449P. doi:10.1007/s00204-020-02836-w. hdl:1854/LU-8687071. PMID 32627074. /wiki/Bibcode_(identifier) ↩

  23. Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR (February 2019). "Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases" (PDF). Drug Test Anal. 11 (2): 318–324. doi:10.1002/dta.2494. PMID 30188017. https://publikationen.sulb.uni-saarland.de/bitstream/20.500.11880/29219/1/Interactions%20of%20phenethylamine-derived%20psychoactive%20substances%20of%20the%202C-series%20with%20human%20monoamine%20oxidases_mit_Vorblatt.pdf ↩

  24. Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1" (PDF). J Pharmacol Exp Ther. 357 (1): 134–144. doi:10.1124/jpet.115.229765. PMID 26791601. https://web.archive.org/web/20250509235235/https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA ↩

  25. Ray TS (February 2010). "Psychedelics and the human receptorome". PLOS ONE. 5 (2): e9019. Bibcode:2010PLoSO...5.9019R. doi:10.1371/journal.pone.0009019. PMC 2814854. PMID 20126400. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2814854 ↩

  26. Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)" (PDF). Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099. https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf ↩

  27. Eshleman AJ, Forster MJ, Wolfrum KM, Johnson RA, Janowsky A, Gatch MB (March 2014). "Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function" (PDF). Psychopharmacology (Berl). 231 (5): 875–888. doi:10.1007/s00213-013-3303-6. PMC 3945162. PMID 24142203. https://www.researchgate.net/profile/Michael-Forster-2/publication/258061356_Behavioral_and_neurochemical_pharmacology_of_six_psychoactive_substituted_phenethylamines_Mouse_locomotion_rat_drug_discrimination_and_in_vitro_receptor_and_transporter_binding_and_function/links/53d119a00cf2f7e53cfbcd68/Behavioral-and-neurochemical-pharmacology-of-six-psychoactive-substituted-phenethylamines-Mouse-locomotion-rat-drug-discrimination-and-in-vitro-receptor-and-transporter-binding-and-function.pdf ↩

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