Ethylisopropyllysergamide

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| image = EiPLA_structure.png

| width = 180

| tradename =

| legal_AU =

| legal_CA =

| legal_DE = NpSG

| legal_UK = PSA

| legal_US =

| legal_US_comment =

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| routes_of_administration =

| CAS_number = 154504-04-8

| PubChem = 101661197

| ChemSpiderID =

| 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

}}

Ethylisopropyllysergamide (EIPLA) is an analog of lysergic acid diethylamide (LSD). In studies in mice, it was found to have approximately half the potency of LSD.{{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 }}{{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 }}{{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 }}