{{Short description|Chemical compound}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | drug_name = EiPLA | image = EiPLA.svg | image_class = skin-invert-image | width = 165px | image2 = EiPLA 3D.png | image_class2 = bg-transparent | width2 = 225px
<!-- Clinical data --> | tradename = | routes_of_administration = Oral<ref name="BrandtKavanaghWestphal2024" /> | class = Serotonin receptor modulator; Serotonin 5-HT<sub>2A</sub> receptor agonist; Serotonergic psychedelic; Hallucinogen
<!-- Legal status --> | legal_AU = | legal_CA = | legal_DE = NpSG | legal_UK = PSA | legal_US = | legal_US_comment = | legal_status =
<!-- Identifiers --> | CAS_number = 154504-04-8 | PubChem = 101661197 | ChemSpiderID = | synonyms = EiPLA; Ethylisopropyllysergamide; ''N''-Ethyl-''N''-isopropyllysergamide; Lysergic acid ethylisopropylamide
<!-- Chemical data --> | IUPAC_name = (6aR,9R)-N-ethyl-7-methyl-N-propan-2-yl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide | C=21 | H=27 | N=3 | O=1 | SMILES = CCN(C(C)C)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C | StdInChI = 1S/C21H27N3O/c1-5-24(13(2)3)21(25)15-9-17-16-7-6-8-18-20(16)14(11-22-18)10-19(17)23(4)12-15/h6-9,11,13,15,19,22H,5,10,12H2,1-4H3/t15-,19-/m1/s1 | StdInChIKey = JLPRDEGOBAGMHN-DNVCBOLYSA-N }}
'''EiPLA''', also known as '''''N''-ethyl-''N''-isopropyllysergamide''' or as '''lysergic acid ethylisopropylamide''', is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD).<ref name="HuangMarona-LewickaPfaff1994" /><ref name="Nichols2018" /><ref name="BrandtKavanaghWestphal2024" /> It is an isomer of ETH-LAD.<ref name="BrandtKavanaghWestphal2024" />
==Use and effects== EiPLA has been identified in blotter containing doses of 86 to 97{{nbsp}}μg base equivalent per tab.<ref name="BrandtKavanaghWestphal2024" /> Blotter containing 200{{nbsp}}μg per tab has also been described.<ref name="BrandtKavanaghWestphal2024" /> Anecdotal reports suggest that EiPLA produces psychedelic effects but is less potent than LSD.<ref name="BrandtKavanaghWestphal2024" />
==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
==Pharmacology== ===Pharmacodynamics=== In drug discrimination tests in rodents, EiPLA was found to have approximately half the potency of LSD.<ref name="HuangMarona-LewickaPfaff1994">{{cite journal | vauthors = Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE | title = Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives | journal = Pharmacology, Biochemistry, and Behavior | volume = 47 | issue = 3 | pages = 667–673 | date = March 1994 | doi = 10.1016/0091-3057(94)90172-4 | pmid = 8208787 }}</ref><ref name="Nichols2018">{{cite journal | vauthors = Nichols DE | title = Dark Classics in Chemical Neuroscience: Lysergic Acid Diethylamide (LSD) | journal = ACS Chemical Neuroscience | volume = 9 | issue = 10 | pages = 2331–2343 | date = October 2018 | doi = 10.1021/acschemneuro.8b00043 | pmid = 29461039 }}</ref><ref name="BrandtKavanaghWestphal2024">{{cite journal | vauthors = Brandt SD, Kavanagh PV, Westphal F, Pulver B, Schwelm HM, Stratford A, Auwärter V, Halberstadt AL | title = Analytical and behavioral characterization of N-ethyl-N-isopropyllysergamide (EIPLA), an isomer of N6 -ethylnorlysergic acid N,N-diethylamide (ETH-LAD) | journal = Drug Testing and Analysis | volume = 16 | issue = 2 | pages = 187–198 | date = February 2024 | pmid = 37321559 | doi = 10.1002/dta.3530 }}</ref>
==Chemistry== ===Analogues=== Analogues of EiPLA include MiPLA, LAMPA (MPLA), EPLA, EcPLA, and ETFELA, among others.<ref name="BrandtKavanaghWestphal2024" /><ref name="WachełkoNowakTusiewicz2025">{{cite journal | vauthors = Wachełko O, Nowak K, Tusiewicz K, Zawadzki M, Szpot P | title = A highly sensitive UHPLC-MS/MS method for determining 15 designer LSD analogs in biological samples with application to stability studies | journal = Analyst | volume = 150 | issue = 2 | pages = 290–308 | date = January 2025 | pmid = 39636448 | doi = 10.1039/d4an01361a | url = }}</ref>
==History== EiPLA was first described in the scientific literature by David E. Nichols and colleagues by at least 1994.<ref name="HuangMarona-LewickaPfaff1994" /> It appears to have emerged as a novel designer drug by 2019.<ref name="BrandtKavanaghWestphal2024" />
==See also== * Substituted lysergamide * Lizard Labs
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/5569 EiPLA - Isomer Design] * [https://www.bluelight.org/xf/threads/873089 The Big & Dandy EiPLA Thread - Bluelight]
{{Psychedelics}} {{Serotonin receptor modulators}} {{Ergolines}}
Category:5-HT2A agonists Category:Carboxamides Category:David E. Nichols Category:Designer drugs Category:Ethyl compounds Category:Isopropyl compounds Category:Lizard Labs Category:Methyl compounds Category:Psychedelic lysergamides Category:Serotonin receptor modulators