{{Short description|Chemical compound}} {{Drugbox | verifiedrevid = 447430848 | drug_name = EiPT | image = Ethylisopropyltryptamine.svg | image_class = skin-invert-image | width = 200px | image2 = EiPT 3D.png | image_class2 = bg-transparent | width2 = 225px
<!-- Clinical data --> | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | routes_of_administration = Oral<ref name="TiHKAL" /> | class = Psychedelic drug; Serotonergic psychedelic
<!-- Legal status --> | legal_AU = | legal_CA = | legal_DE = NpSG | legal_UK = Class A | legal_US = | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | onset = | elimination_half-life = | duration_of_action = 4–6 hours<ref name="TiHKAL" /> | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 848130-11-0 | ATC_prefix = none | ATC_suffix = | PubChem = 44719455 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 21106305 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 63J8CXV5Z8 | synonyms = EiPT; ''N''-Ethyl-''N''-isopropyltryptamine
<!-- Chemical data --> | IUPAC_name = N-ethyl-N-[2-(1H-indol-3-yl)ethyl]propan-2-amine | C=15 | H=22 | N=2 | SMILES = CCN(C(C)C)CCc1c[nH]c2ccccc12 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C15H22N2/c1-4-17(12(2)3)10-9-13-11-16-15-8-6-5-7-14(13)15/h5-8,11-12,16H,4,9-10H2,1-3H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = HQZLBYMOYCJZRF-UHFFFAOYSA-N
<!-- Physical data --> | melting_point = 71 | melting_high = 73 }}
'''Ethylisopropyltryptamine''' ('''EiPT'''), also known as '''''N''-ethyl-''N''-isopropyltryptamine''', is a psychedelic drug of the tryptamine family.<ref name="TiHKAL">{{CiteTiHKAL}} https://www.erowid.org/library/books_online/tihkal/tihkal10.shtml</ref> It is taken orally.<ref name="TiHKAL" />
EiPT appears to have been first synthesized and described by Alexander Shulgin.<ref name="TiHKAL" />
==Use and effects== In his book ''TiHKAL'' (''Tryptamines I Have Known and Loved''), Alexander Shulgin lists the dose of EiPT as 24 to 40{{nbsp}}mg and its duration as 4 to 6{{nbsp}}hours.<ref name="TiHKAL" /> According to Shulgin, this compound tends to produce nausea, dysphoria, and other unpleasant side effects.<ref name="TiHKAL" /> It also seems to largely lack the hallucinatory and visual properties usually associated with psychedelic drugs.<ref name="TiHKAL" />
==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
==Chemistry== EiPT is short for ''N''-ethyl-''N''-isopropyltryptamine.<ref name="TiHKAL" /> The full chemical name of this structure is ''N''-ethyl-''N''-[2-(1''H''-indol-3-yl)ethyl]propan-2-amine. The compound is a substituted tryptamine, which all belong to a larger family of compounds known as indolethylamines.<ref name="TiHKAL" />
===Synthesis=== The chemical synthesis of EiPT has been described.<ref name="TiHKAL" />
===Analogues=== Analogues of EiPT include 4-HO-EiPT, 4-AcO-EiPT, 5-MeO-EiPT, methylisopropyltryptamine (MiPT), propylisopropyltryptamine (PiPT), ethylpropyltryptamine (EPT), diethyltryptamine (DET), and diisopropyltryptamine (DiPT), among others.<ref name="TiHKAL" />
==Society and culture== ===Legal status=== ====United States==== EiPT is unscheduled and uncontrolled in the United States, but possession and sales of EiPT could be prosecuted under the Federal Analog Act because of its structural similarities to DET.{{Citation needed|date=October 2025}}
==See also== * Substituted tryptamine
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/5010 EIPT - Isomer Design] * [https://www.erowid.org/library/books_online/tihkal/tihkal10.shtml EiPT - TiHKAL - Erowid] * [http://tihkal.info/read.php?domain=tk&id=10 EiPT - TiHKAL - Isomer Design]
{{Psychedelics}} {{Tryptamines}}
Category:Designer drugs Category:N,N-Dialkyltryptamines Category:Isopropylamino compounds Category:Psychedelic tryptamines Category:TiHKAL