# EcPLA
> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/EcPLA
> Markdown URL: https://mediated.wiki/source/EcPLA.md
> Source: https://en.wikipedia.org/wiki/EcPLA
> Source revision: 1339774515
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)
{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| image = ECPLA.svg
| image_class = skin-invert-image
| width = 165px
| image2 = EcPLA 3D.png
| image_class2 = bg-transparent
| width2 = 225px
| tradename =
| routes_of_administration = [Oral](/source/Oral_administration)
| class = [Serotonin receptor modulator](/source/Serotonin_receptor_modulator); [Serotonin 5-HT2A receptor agonist](/source/Serotonin_5-HT2A_receptor_agonist); [Serotonergic psychedelic](/source/Serotonergic_psychedelic); [Hallucinogen](/source/Hallucinogen)
| legal_AU =
| legal_CA =
| legal_DE = NpSG
| legal_UK = PSA
| legal_US =
| legal_US_comment =
| legal_status = Illegal in France[{{cite web | title = Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants | date = 20 May 2021 | url = https://www.legifrance.gouv.fr/jorf/id/JORFTEXT000043523554 | website = www.legifrance.gouv.fr | lang = fr }}]
| CAS_number = 2349367-50-4
| PubChem = 163184957
| ChemSpiderID = 129395457
| synonyms = ECYPLA; ''N''-Ethyl-''N''-cyclopropyllysergamide; Lysergic acid ethylcyclopropylamide; LAEcP
| IUPAC_name = (6a''R'',9''R'')-''N''-cyclopropyl-''N''-ethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-''fg'']quinoline-9-carboxamide
| C=21 | H=25 | N=3 | O=1
| SMILES = CCN(C1CC1)C(=O)[C@@H]3C=C2c4cccc5ncc(C[C@H]2N(C)C3)c45
| StdInChI = 1S/C21H25N3O/c1-3-24(15-7-8-15)21(25)14-9-17-16-5-4-6-18-20(16)13(11-22-18)10-19(17)23(2)12-14/h4-6,9,11,14-15,19,22H,3,7-8,10,12H2,1-2H3/t14-,19-/m1/s1
| StdInChIKey = UNUJKEQFYPYXBK-AUUYWEPGSA-N
}}
'''EcPLA''', also known as '''''N''-ethyl-''N''-cyclopropyllysergamide''' or as '''lysergic acid ethylcyclopropylamide''' ('''LAEcP'''), is a [psychedelic drug](/source/psychedelic_drug) of the [lysergamide](/source/substituted_lysergamide) family related to [lysergic acid diethylamide](/source/lysergic_acid_diethylamide) (LSD).[{{Cite journal | vauthors = Kavanagh PV, Westphal F, Stratford A, Elliott SP, Dowling G, Halberstadt AL, Brandt SD | title = Analytical profile of N-ethyl-N-cyclopropyl lysergamide (ECPLA), an isomer of lysergic acid 2,4-dimethylazetidide (LSZ) | journal = Drug Testing and Analysis | volume = 12 | issue = 10 | pages = 1514–1521 | date = 2020 | pmid = 32803833 | pmc = 9191644 | doi = 10.1002/dta.2911 | language = en | issn = 1942-7611 }}][{{cite web | title=ECPLA | website=АИПСИН | url=https://aipsin.com/newsubstance/831/ | language=ru | access-date=1 January 2026}}] It is an [isomer](/source/isomer) of [LSZ](/source/LSZ_(drug)) and is closely related to other [amide](/source/amide)-substituted lysergamides like [MiPLA](/source/MiPLA).[{{cite journal | vauthors = Halberstadt AL, Klein LM, Chatha M, Valenzuela LB, Stratford A, Wallach J, Nichols DE, Brandt SD | title = Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA) | journal = Psychopharmacology | volume = 236 | issue = 2 | pages = 799–808 | date = February 2019 | pmid = 30298278 | pmc = 6848745 | doi = 10.1007/s00213-018-5117-z }}]
The drug produces the [head-twitch response](/source/head-twitch_response), a behavioral proxy of [psychedelic](/source/psychedelic_drug) effects, in rodents. It has about 40% of the potency of LSD in this regard.[{{cite journal | vauthors = Wagmann L, Richter LH, Kehl T, Wack F, Bergstrand MP, Brandt SD, Stratford A, Maurer HH, Meyer MR | title = In vitro metabolic fate of nine LSD-based new psychoactive substances and their analytical detectability in different urinary screening procedures | journal = Analytical and Bioanalytical Chemistry | volume = 411 | issue = 19 | pages = 4751–4763 | date = July 2019 | pmid = 30617391 | doi = 10.1007/s00216-018-1558-9 | s2cid = 58615418 | url = http://researchonline.ljmu.ac.uk/id/eprint/9841/13/ABC-01967-2018_02_accepted.pdf }}]
==Chemistry==
===Analogues===
[Analogue](/source/Structural_analog)s of EcPLA include [MiPLA](/source/methylisopropyllysergamide), [LAMPA](/source/methylpropyllysergamide) (MPLA), [EPLA](/source/ethylpropyllysergamide), [EiPLA](/source/ethylisopropyllysergamide), [ETFELA](/source/ethyltrifluoroethyllysergamide), and [LSZ](/source/LSZ_(drug)), among others.[{{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 = }}]