Editing 2C-E

{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 477216166
| drug_name = 
| image = 2C-E.svg
| width = 
| caption = 
| image2 = 2C-E-3d-sticks.png
| width2 = 
| caption2 = 

<!-- Clinical data -->
| pronounce = 
| tradename = 
| Drugs.com = 
| MedlinePlus = 
| licence_CA = 
| licence_EU = 
| DailyMedID = 
| licence_US = 
| pregnancy_AU = 
| pregnancy_category = 
| dependency_liability = 
| addiction_liability = 
| routes_of_administration = [[Oral administration|Oral]]
| class = [[Serotonin]] [[5-HT2 receptor|5-HT<sub>2</sub> receptor]] [[agonist]]; [[Serotonergic psychedelic]]; [[Hallucinogen]]
| ATC_prefix = None
| ATC_suffix = 

<!-- Legal status -->
| legal_BR = F2
| legal_CA = Schedule III
| legal_DE = Anlage I
| legal_NZ = Class C
| legal_UK = Class A
| legal_US = Schedule I
| legal_status = 

<!-- Pharmacokinetic data -->
| bioavailability = 
| protein_bound = 
| metabolism = 
| metabolites = 
| onset = 
| elimination_half-life = 
| duration_of_action = 
| excretion = 

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 71539-34-9
| CAS_supplemental = 
| PubChem = 24729233
| PubChemSubstance = 
| IUPHAR_ligand = 
| DrugBank = 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106222
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = I190284UXX
| KEGG = 
| ChEBI = 
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 124063
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = 2,5-Dimethoxy-4-ethylphenethylamine; 4-Ethyl-2,5-dimethoxyphenethylamine; Aquarust

<!-- Chemical data -->
| IUPAC_name = 2-(4-ethyl-2,5-dimethoxyphenyl)ethan-1-amine
| C=12 | H=19 | N=1 | O=2 
| SMILES = COc1cc(CC)c(cc1CCN)OC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H19NO2/c1-4-9-7-12(15-3)10(5-6-13)8-11(9)14-2/h7-8H,4-6,13H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VDRGNAMREYBIHA-UHFFFAOYSA-N

<!-- Physical data -->
| solubility = >70
}}

'''2C-E''' is a [[Psychedelic drug|psychedelic]] [[phenethylamines|phenethylamine]] of the [[2C (psychedelics)|2C family]]. It was first synthesized by [[Alexander Shulgin]]<ref name="PiHKAL">{{CitePiHKAL}} [https://www.erowid.org/library/books_online/pihkal/pihkal024.shtml 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>{{cite journal | vauthors = Papaseit E, Olesti E, Pérez-Mañá C, Torrens M, Grifell M, Ventura M, Pozo OJ, de Sousa Fernandes Perna EB, Ramaekers JG, de la Torre R, Farré M | title = Acute Effects of 2C-E in Humans: An Observational Study | journal = Frontiers in Pharmacology | volume = 11 | pages = 233 | date = 2020 | pmid = 32256350 | pmc = 7093582 | doi = 10.3389/fphar.2020.00233 | doi-access = free }}</ref>

==Use and dosage==
Shulgin gives the dose range of 2C-E as 10 to 25{{nbsp}}mg.<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" />

==Effects==
According to Shulgin, the [[duration of action|duration]] of 2C-E's effects is 8 to 12{{nbsp}}hours.<ref name=PiHKAL/>

2C-E's effects are often described as "neutral", in comparison with other psychedelic chemicals and even other [[2C (psychedelics)|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 effects==
Adverse effects include [[tachycardia]], [[hypertension]],  [[Psychomotor agitation|agitation]], [[delirium]], and [[hallucination]]s.<ref name=Topeff>{{cite journal | author1 = Topeff JM | author2 = Ellsworth H | author3 = Willhite LA | author4 = Bangh SA | author5 = Edwards EM | author6 = Cole JB | title = A case series of symptomatic patients, including one fatality, following 2C-E exposure | journal = Clin. Toxicol. | date = 2011 | volume = 49 | page = 526}}</ref>  At least two deaths have been attributed to a 2C-E overdose.<ref name=Topeff/><ref>{{cite news| vauthors = Pham S |title=Man Arrested in Mass Drug Overdose That Killed 1 Teen and Left 10 People Hospitalized|url=https://abcnews.go.com/US/man-arrested-minnesota-deadly-mass-drug-overdose/story?id=13166375|access-date=29 June 2014|work=ABC World News|date=18 March 2011}}</ref><ref name=Sacks>{{cite journal | author1 = Sacks J | author2 = Ray MJ | author3 = Williams S | author4 = Opatowsky MJ | title = Fatal toxic leukoencephalopathy secondary to overdose of a new psychoactive designer drug 2C-E ("Europa") | journal = Baylor University Medical Center Proceedings | date = 2012 | volume = 25 | issue = 4| pages = 374–376 | doi = 10.1080/08998280.2012.11928883 | pmid = 23077393 | pmc = 3448584 }}</ref>

==Interactions==
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

2C-E is [[drug metabolism|metabolized]] by the [[monoamine oxidase]] (MAO) [[enzyme]]s [[MAO-A]] and [[MAO-B]].<ref name="DeanStellpflugBurnett2013">{{cite journal | vauthors = Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM | title = 2C or not 2C: phenethylamine designer drug review | journal = J Med Toxicol | volume = 9 | issue = 2 | pages = 172–178 | date = June 2013 | pmid = 23494844 | pmc = 3657019 | doi = 10.1007/s13181-013-0295-x | url = }}</ref><ref name="TheobaldMaurer2007">{{cite journal | vauthors = Theobald DS, Maurer HH | title = Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series) | journal = Biochem Pharmacol | volume = 73 | issue = 2 | pages = 287–297 | date = January 2007 | pmid = 17067556 | doi = 10.1016/j.bcp.2006.09.022 | url = }}</ref> [[Monoamine oxidase inhibitor]]s (MAOIs) such as [[phenelzine]], [[tranylcypromine]], [[moclobemide]], and [[selegiline]] may potentiate the effects of 2C-E.<ref name="DeanStellpflugBurnett2013" /><ref name="TheobaldMaurer2007" /><ref name="HalmanKongSarris2024">{{Cite journal |vauthors=Halman A, Kong G, Sarris J, Perkins D |date=January 2024 |title=Drug-drug interactions involving classic psychedelics: A systematic review |journal=J Psychopharmacol |volume=38 |issue=1 |pages=3–18 |doi=10.1177/02698811231211219 |pmc=10851641 |pmid=37982394}}</ref> This may result in [[overdose]] and serious [[toxicity]].<ref name="HalmanKongSarris2024" /><ref name="DeanStellpflugBurnett2013" />

==Pharmacology==
===Pharmacodynamics===
{| class="wikitable floatleft" style="font-size:small;"
|+ {{Nowrap|2C-E activities}}
|-
! [[Biological target|Target]] !! [[Affinity (pharmacology)|Affinity]] (K<sub>i</sub>, nM)
|-
| [[5-HT1A receptor|5-HT<sub>1A</sub>]] || 307–1,190 (K<sub>i</sub>)<br />>10,000 ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}})<br /><20% ({{Abbrlink|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT1B receptor|5-HT<sub>1B</sub>]] || 253
|-
| [[5-HT1D receptor|5-HT<sub>1D</sub>]] || 73.2
|-
| [[5-HT1E receptor|5-HT<sub>1E</sub>]] || 626
|-
| [[5-HT1F receptor|5-HT<sub>1F</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT2A receptor|5-HT<sub>2A</sub>]] || 4.5–43.9 (K<sub>i</sub>)<br />2.5–84 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />40–87% ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT2B receptor|5-HT<sub>2B</sub>]] || 25.1 (K<sub>i</sub>)<br />190 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />66% ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT2C receptor|5-HT<sub>2C</sub>]] || 5.4–104 (K<sub>i</sub>)<br />0.23–18.0 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />98–106% ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT3 receptor|5-HT<sub>3</sub>]] || >10,000
|-
| [[5-HT4 receptor|5-HT<sub>4</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT5A receptor|5-HT<sub>5A</sub>]] || >10,000
|-
| [[5-HT6 receptor|5-HT<sub>6</sub>]] || 2,971
|-
| [[5-HT7 receptor|5-HT<sub>7</sub>]] || 426
|-
| [[Alpha-1A adrenergic receptor|α<sub>1A</sub>]] || 7,400–>10,000
|-
| [[Alpha-1B adrenergic receptor|α<sub>1B</sub>]] || >10,000
|-
| [[Alpha-1D adrenergic receptor|α<sub>1D</sub>]] || {{Abbr|ND|No data}}
|-
| [[Alpha-2A adrenergic receptor|α<sub>2A</sub>]] || 100–490
|-
| [[Alpha-2B adrenergic receptor|α<sub>2B</sub>]] || 306
|-
| [[Alpha-2C adrenergic receptor|α<sub>2C</sub>]] || 90.2
|-
| [[Beta-1 adrenergic receptor|β<sub>1</sub>]] || >10,000
|-
| [[Beta-2 adrenergic receptor|β<sub>2</sub>]] || {{Abbr|ND|No data}}
|-
| [[Beta-3 adrenergic receptor|β<sub>3</sub>]] || {{Abbr|ND|No data}}
|-
| [[D1 receptor|D<sub>1</sub>]] || >10,000
|-
| [[D2 receptor|D<sub>2</sub>]] || 3,200–3,339
|-
| [[D3 receptor|D<sub>3</sub>]] || 1,345–19,000
|-
| [[D4 receptor|D<sub>4</sub>]] || >10,000
|-
| [[D5 receptor|D<sub>5</sub>]] || >10,000
|-
| [[H1 receptor|H<sub>1</sub>]]–[[H4 receptor|H<sub>4</sub>]] || >10,000
|-
| [[Muscarinic acetylcholine M1 receptor|M<sub>1</sub>]] || >10,000
|-
| [[M2 receptor|M<sub>2</sub>]] || >10,000
|-
| [[Muscarinic acetylcholine M3 receptor|M<sub>3</sub>]] || 2,557
|-
| [[M4 receptor|M<sub>4</sub>]] || >10,000
|-
| [[M5 receptor|M<sub>5</sub>]] || 1,725
|-
| [[I1 receptor|I<sub>1</sub>]] || >10,000
|-
| [[Sigma-1 receptor|σ<sub>1</sub>]] || {{Abbr|ND|No data}}
|-
| [[Sigma-2 receptor|σ<sub>2</sub>]] || >10,000
|-
| {{Abbrlink|TAAR1|Trace amine-associated receptor 1}} || 1,200 (K<sub>i</sub>) (mouse)<br />66–70 (K<sub>i</sub>) (rat)<br />1,100 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (mouse)<br />180 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (rat)<br />6,410–>10,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (human)<br />64% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) (mouse)<br />72% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) (rat)
|-
| {{Abbrlink|SERT|Serotonin transporter}} || >10,000 (K<sub>i</sub>)<br />62,000–72,000 ({{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />>100,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
| {{Abbrlink|NET|Norepinephrine transporter}} || >10,000 (K<sub>i</sub>)<br />26,000–89,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />>100,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
| {{Abbrlink|DAT|Dopamine transporter}} || >10,000 (K<sub>i</sub>)<br />275,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />>100,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
| {{Abbrlink|MAO-A|Monoamine oxidase A}} || {{Abbr|ND|No data}} ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})
|-
| {{Abbrlink|MAO-B|Monoamine oxidase B}} || 124,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})
|- class="sortbottom"
| colspan="2" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''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">{{cite web | title=Kᵢ Database | website=PDSP | date=16 March 2025 | url=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= | access-date=16 March 2025}}</ref><ref name="BindingDB">{{cite web | vauthors = Liu T | title=BindingDB BDBM50240788 2-(2,5-dimethoxy-4-ethylphenyl)ethylamine::2-(4-Ethyl-2,5-dimethoxy-phenyl)-ethylamine::CHEMBL124063::US20240166618, Compound 2C-E | website=BindingDB | url=https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50240788 | access-date=3 March 2025}}</ref><ref name="Ray2010">{{cite journal | vauthors = Ray TS | title = Psychedelics and the human receptorome | journal = PLOS ONE | volume = 5 | issue = 2 | pages = e9019 | date = February 2010 | pmid = 20126400 | pmc = 2814854 | doi = 10.1371/journal.pone.0009019 | doi-access = free | bibcode = 2010PLoSO...5.9019R | url = }}</ref><ref name="RickliLuethiReinisch2015">{{cite journal | vauthors = Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME | title = Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs) | journal = Neuropharmacology | volume = 99 | issue = | pages = 546–553 | date = December 2015 | pmid = 26318099 | doi = 10.1016/j.neuropharm.2015.08.034 | url = 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}}</ref><ref name="EshlemanForsterWolfrum2014">{{cite journal | vauthors = Eshleman AJ, Forster MJ, Wolfrum KM, Johnson RA, Janowsky A, Gatch MB | title = Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function | journal = Psychopharmacology (Berl) | volume = 231 | issue = 5 | pages = 875–888 | date = March 2014 | pmid = 24142203 | pmc = 3945162 | doi = 10.1007/s00213-013-3303-6 | url = 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}}</ref><ref name="NagaiNonakaSatohHisashiKamimura2007">{{cite journal | vauthors = Nagai F, Nonaka R, Satoh Hisashi Kamimura K | title = The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain | journal = Eur J Pharmacol | volume = 559 | issue = 2–3 | pages = 132–137 | date = March 2007 | pmid = 17223101 | doi = 10.1016/j.ejphar.2006.11.075 | url = }}</ref><ref name="PottieCannaertStove2020">{{cite journal | vauthors = Pottie E, Cannaert A, Stove CP | title = In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor | journal = Arch Toxicol | volume = 94 | issue = 10 | pages = 3449–3460 | date = October 2020 | pmid = 32627074 | doi = 10.1007/s00204-020-02836-w | bibcode = 2020ArTox..94.3449P | url = | hdl = 1854/LU-8687071 | hdl-access = free }}</ref><ref name="WagmannBrandtStratford2019">{{cite journal | vauthors = Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR | title = Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases | journal = Drug Test Anal | volume = 11 | issue = 2 | pages = 318–324 | date = February 2019 | pmid = 30188017 | doi = 10.1002/dta.2494 | url =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 }}</ref><ref name="SimmlerBuchyChaboz2016">{{cite journal | vauthors = Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME | title = In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1 | journal = J Pharmacol Exp Ther | volume = 357 | issue = 1 | pages = 134–144 | date = April 2016 | pmid = 26791601 | doi = 10.1124/jpet.115.229765 | url = 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 | archive-url = 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 | url-status = dead | archive-date = 2025-05-09 }}</ref>
|}

2C-E acts as a [[serotonin]] [[5-HT2 receptor|5-HT<sub>2</sub> receptor]] [[agonist]].<ref name="Ray2010" /><ref name="RickliLuethiReinisch2015" /> Activation of the serotonin [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] is thought to be responsible for its [[psychedelic drug|psychedelic]] effects.{{Citation needed|date=March 2025}}

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" />

==Chemistry==
===Properties===
[[File:MSpectro2C-E.gif|thumb|right|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&nbsp;°C at 0.25&nbsp;mmHg pressure was collected and converted to the hydrochloride salt. Shulgin reports the melting point of the hydrochloride salt as 208.5–210.5&nbsp;°C.<ref name="shulginIndex">{{cite book| vauthors = Shulgin AT, Manning T, Daley PF|title=[[The Shulgin Index|The Shulgin Index: Volume 1]]|date=2011|publisher=Transform Press|location=Berkeley, CA|isbn=978-0-9630096-3-0|edition=First}}</ref>

==Society and culture==
===Legal status===
[[File:ethylphenethylamine.jpg|thumb|right|20&nbsp;mg capsules of 2C-E.]]
[[File:2,5-dimethoxy-4-ethyl.jpg|thumb|right|2C-E pile.]]

====Australia====
In [[Queensland]], 2C-E was added to the 'Dangerous Drugs' list of the 'Drugs Misuse Act 1986'<ref>{{cite web|url=https://www.legislation.qld.gov.au/LEGISLTN/CURRENT/D/DrugsMisuseA86.pdf|title=In force legislation - Queensland Legislation - Queensland Government|website=legislation.qld.gov.au|url-status=live|archive-url=https://web.archive.org/web/20140911060554/https://www.legislation.qld.gov.au/LEGISLTN/CURRENT/D/DrugsMisuseA86.pdf|archive-date=2014-09-11}}</ref> by the 'Drugs Misuse Amendment Act 2008'.<ref>{{cite web|url=https://www.legislation.qld.gov.au/LEGISLTN/ACTS/2008/08AC004.pdf|title=Acts as passed - Queensland Legislation - Queensland Government|website=legislation.qld.gov.au|url-status=live|archive-url=https://web.archive.org/web/20150407024051/https://www.legislation.qld.gov.au/LEGISLTN/ACTS/2008/08AC004.pdf|archive-date=2015-04-07}}</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>{{cite periodical |url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php |periodical=Canada Gazette |volume=150 |issue=9 |title=Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines) |date=4 May 2016|url-status=live|archive-url=https://web.archive.org/web/20160831014117/http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php|archive-date=2016-08-31}}</ref>

====China====
As of October 2015, 2C-E is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 }}</ref>

====Denmark====
2C-E is added to the list of Schedule B controlled substances.<ref>{{cite web|url=https://www.retsinformation.dk/Forms/R0710.aspx?id=137169|title=Bekendtgørelse om euforiserende stoffer - retsinformation.dk<!-- Bot generated title -->|last=Sundheds- og Ældreministeriet|website=retsinformation.dk|url-status=live|archive-url=https://web.archive.org/web/20131004215445/https://www.retsinformation.dk/Forms/R0710.aspx?id=137169|archive-date=2013-10-04}}</ref>

====Finland====
Scheduled in "government decree on psychoactive substances banned from the consumer market".<ref>{{cite web | url=https://finlex.fi/fi/lainsaadanto/2014/1130 | title=1130/2014 }}</ref>

====Germany====
2C-E is an [[Drugs controlled by the German Betäubungsmittelgesetz|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.{{CN|date=November 2023}} However production and distribution (buying/selling) are a criminal offense.

====Sweden====
[[Riksdag|''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>{{cite web |url=http://www.notisum.se/rnp/sls/sfs/20040696.pdf |title=20040696 |access-date=2013-09-06 |url-status=live |archive-url=https://web.archive.org/web/20130929063316/http://www.notisum.se/rnp/sls/sfs/20040696.pdf |archive-date=2013-09-29 }}</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 controlled substance|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">{{cite web|url=https://www.erowid.org/chemicals/2ce/2ce_law.shtml|title=Erowid 2C-E Vault: Legal Status|website=erowid.org|url-status=live|archive-url=https://web.archive.org/web/20151208043457/https://www.erowid.org/chemicals/2ce/2ce_law.shtml|archive-date=2015-12-08}}</ref>

==Notes==
<references group="nb" />

==References==
{{Reflist}}

==External links==
* [https://isomerdesign.com/pihkal/explore/24 2C-E - Isomer Design]
* [https://psychonautwiki.org/wiki/2C-E 2C-E - PsychonautWiki]
* [https://www.erowid.org/chemicals/2ce/ Erowid 2C–E vault]
* [https://tripsitter.com/2ce/ 2C-E: Psychedelic Information & Safety - Tripsitter]
* [https://web.archive.org/web/20140305212114/http://www.maps.org/t2e/c6.html Chapter in Myron J. Stolaroff's ''Thanatos To Eros, 35 Years of Psychedelic Exploration'' discussing author's experiments with 2C-E]

{{Psychedelics}}
{{Serotonin receptor modulators}}
{{TAAR modulators}}
{{Phenethylamines}}

[[Category:2C (psychedelics)]]
[[Category:5-HT2A agonists]]
[[Category:5-HT2B agonists]]
[[Category:5-HT2C agonists]]
[[Category:Alexander Shulgin]]
[[Category:Designer drugs]]
[[Category:O-methylated phenols]]
[[Category:Psychedelic phenethylamines]]
[[Category:TAAR1 agonists]]