{{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | verifiedrevid = 399915146 | drug_name = EEE | image = EEE structure.svg | image_class = skin-invert-image | width = 250px | image2 = EEE-3d-sticks.png | image_class2 = bg-transparent | width2 = 235px
<!-- 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 = Unknown<ref name="PiHKAL" /> | class = | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = Unknown<ref name="PiHKAL" /> | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 23693-42-7 | CAS_supplemental = | PubChem = 44719557 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 21106296 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = DY8NEE4XXW | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = 2,4,5-Triethoxyamphetamine; TMA2-2,4,5-TriEtO; TMA2-TriEtO
<!-- Chemical data --> | IUPAC_name = 1-(2,4,5-triethoxyphenyl)propan-2-amine | C=15 | H=25 | N=1 | O=3 | SMILES = CCOc1cc(OCC)c(cc1OCC)CC(C)N | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C15H25NO3/c1-5-17-13-10-15(19-7-3)14(18-6-2)9-12(13)8-11(4)16/h9-11H,5-8,16H2,1-4H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = PVOHHXSVHWUAMS-UHFFFAOYSA-N }}
'''EEE''', also known as '''2,4,5-triethoxyamphetamine''' or as '''TMA2-2,4,5-TriEtO''', is a chemical compound of the phenethylamine, amphetamine, and DOx families.<ref name="PiHKAL">{{Cite book | vauthors = Shulgin AT, Shulgin A | chapter = EEE | title = PiHKAL: A Chemical Love Story | location = Berkeley, CA | year = 1991 | author-link1 = Alexander Shulgin | author-link2 = Ann Shulgin | chapter-url = http://www.erowid.org/library/books_online/pihkal/pihkal073.shtml | publisher = Transform Press | isbn = 978-0-9630096-0-9 | edition = 1st | ol = 22859055M }}</ref><ref name="Shulgin2003">{{cite book | vauthors = Shulgin AT | veditors = Laing RR | chapter = Basic Pharmacology and Effects | title = Hallucinogens: A Forensic Drug Handbook | pages = 67–137 | year = 2003 | publisher = Elsevier Science | series = Forensic Drug Handbook Series | isbn = 978-0-12-433951-4 | url = https://books.google.com/books?id=l1DrqgobbcwC | chapter-url = https://bibliography.maps.org/resources/download/12634 | archive-url = https://web.archive.org/web/20250713013624/https://bibliography.maps.org/resources/download/12634 | archive-date = 13 July 2025 }}</ref><ref name="Shulgin1968">{{cite journal | vauthors = Shulgin AT | title = The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine | journal = J Med Chem | volume = 11 | issue = 1 | pages = 186–187 | date = January 1968 | pmid = 5637180 | doi = 10.1021/jm00307a056 | url = https://bibliography.maps.org/resources/download/8618 | archive-url = https://web.archive.org/web/20250712213354/https://bibliography.maps.org/resources/download/8618 | archive-date = 2025-07-12}}</ref><ref name="ShulginSargentNaranjo1969">{{cite journal | vauthors = Shulgin AT, Sargent T, Naranjo C | title = Structure–activity relationships of one-ring psychotomimetics | journal = Nature | volume = 221 | issue = 5180 | pages = 537–541 | date = February 1969 | pmid = 5789297 | doi = 10.1038/221537a0 | bibcode = 1969Natur.221..537S | url = https://bibliography.maps.org/resources/download/11267 | archive-url = https://web.archive.org/web/20250712213646/https://bibliography.maps.org/resources/download/11267 | archive-date = 2025-07-12}}</ref> It is the analogue of TMA-2 in which the three methoxy groups on the phenyl ring have been replaced with ethoxy groups.<ref name="PiHKAL" /><ref name="Shulgin1968" /><ref name="ShulginSargentNaranjo1969" /> In his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved''), Alexander Shulgin lists EEE's dose and duration as unknown.<ref name="PiHKAL" /> Shulgin stated that EEE has never been tested in humans.<ref name="PiHKAL" /><ref name="Shulgin2003" /> The chemical synthesis of EEE has been described.<ref name="PiHKAL" /><ref name="Shulgin1968" /> EEE was first described in the scientific literature by Shulgin in 1968.<ref name="Shulgin1968" /> Subsequently, it was described in greater detail by Shulgin in ''PiHKAL'' in 1991.<ref name="PiHKAL" />
==See also== * DOx (psychedelics) * TWEETIO § DOx compounds * EEM, EME, and MEE
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/73 EEE - Isomer Design] * [https://www.erowid.org/library/books_online/pihkal/pihkal073.shtml EEE - PiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/pk/73 EEE - PiHKAL - Isomer Design]
{{Phenethylamines}}
Category:Ethoxy compounds Category:Phenol ethers Category:PiHKAL Category:Substituted amphetamines
{{Hallucinogen-stub}}