{{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
<!-- Clinical data --> | tradename = | routes_of_administration = Oral | 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 = Illegal in France<ref>{{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 }}</ref>
<!-- Identifiers --> | CAS_number = 2349367-50-4 | PubChem = 163184957 | ChemSpiderID = 129395457 | synonyms = ECYPLA; ''N''-Ethyl-''N''-cyclopropyllysergamide; Lysergic acid ethylcyclopropylamide; LAEcP
<!-- Chemical data --> | 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 of the lysergamide family related to lysergic acid diethylamide (LSD).<ref name="KavanaghWestphalStratford2020">{{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 }}</ref><ref name="HalberstadtKleinChatha2019" /><ref name="Aipsin">{{cite web | title=ECPLA | website=АИПСИН | url=https://aipsin.com/newsubstance/831/ | language=ru | access-date=1 January 2026}}</ref> It is an isomer of LSZ and is closely related to other amide-substituted lysergamides like MiPLA.<ref name="HalberstadtKleinChatha2019" /><ref name="KavanaghWestphalStratford2020" /><ref name="WachełkoNowakTusiewicz2025" /><ref name="Aipsin" /> The drug has been encountered as a novel designer drug.<ref name="Aipsin" />
==Use and effects== EcPLA produces psychedelic effects in humans.<ref name="Aipsin" />
==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
==Pharmacology== ===Pharmacodynamics=== EcPLA has been found to interact with serotonin receptors and dopamine receptors, among other targets. It is a high potency agonist of the serotonin receptors, with its highest binding affinities at the 5-HT{{sub|1A}} ({{mvar|K{{sub|i}}}} = {{val|3.2|u=nM}}), 5-HT{{sub|2B}} ({{mvar|K{{sub|i}}}} = {{val|5.3|u=nM}}), and 5-HT{{sub|5A}} ({{mvar|K{{sub|i}}}} = {{val|8.6|u=nM}}) subtypes. Its 5-HT{{sub|2A}} affinity is equivalent to that of LSD, while the affinity to 5-HT{{sub|2C}} receptors is 3 times lower than LSD. It shares much of its binding profile with LSD, but does not bind to β1 or β2 adrenergic receptors as LSD does.<ref name="HalberstadtKleinChatha2019">{{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 }}</ref>
The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. It has about 40% of the potency of LSD in this regard.<ref name="HalberstadtKleinChatha2019"/>
===Pharmacokinetics=== The ''in-vitro'' metabolism of EcPLA has been studied.<ref name="WagmannRichterKehl2019">{{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 }}</ref>
==Chemistry== ===Analogues=== Analogues of EcPLA include MiPLA, LAMPA (MPLA), EPLA, EiPLA, ETFELA, and LSZ, among others.<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><ref name="HalberstadtKleinChatha2019" /><ref name="KavanaghWestphalStratford2020" />
==History== EcPLA was first described in the scientific literature by a team that included Adam Halberstadt, Alexander Stratford, Jason Wallach, and David E. Nichols in 2019.<ref name="HalberstadtKleinChatha2019" /> It was developed by Lizard Labs.{{Citation needed|date=October 2025}} The drug was encountered online as a novel designer drug in around 2020 and became more widely available in early 2022.<ref name="Aipsin" />
== See also == * Substituted lysergamide * Lizard Labs
== References == {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/2843 ECPLA - Isomer Design]
{{Psychedelics}} {{Serotonin receptor modulators}} {{Dopamine receptor modulators}} {{Ergolines}}
Category:5-HT2A agonists Category:5-HT2B agonists Category:5-HT2C agonists Category:Carboxamides Category:Cyclopropyl compounds Category:Designer drugs Category:Dopamine receptor modulators Category:Ethyl compounds Category:Lizard Labs Category:Methyl compounds Category:Psychedelic lysergamides Category:Serotonin receptor modulators