EcPLA

EcPLA
Clinical data
Other names	ECYPLA; N-Ethyl-N-cyclopropyllysergamide; Lysergic acid ethylcyclopropylamide; LAEcP
Routes of; administration	Oral
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act; Illegal in France;
Identifiers
	IUPAC name (6aR,9R)-N-cyclopropyl-N-ethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide;
CAS Number	2349367-50-4;
PubChem CID	163184957;
ChemSpider	129395457;
Chemical and physical data
Formula	C21H25N3O
Molar mass	335.451 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(C1CC1)C(=O)[C@@H]3C=C2c4cccc5ncc(C[C@H]2N(C)C3)c45;
	InChI InChI=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; Key: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).^[2]^[3]^[4] It is an isomer of LSZ and is closely related to other amide-substituted lysergamides like MiPLA.^[3]^[2]^[5]^[4] The drug has been encountered as a novel designer drug.^[4]

Use and effects

EcPLA produces psychedelic effects in humans.^[4]

Interactions

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_1A ( $K i$ = 3.2 nM), 5-HT_2B ( $K i$ = 5.3 nM), and 5-HT_5A ( $K i$ = 8.6 nM) subtypes. Its 5-HT_2A affinity is equivalent to that of LSD, while the affinity to 5-HT_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.^[3]

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.^[3]

Pharmacokinetics

The in-vitro metabolism of EcPLA has been studied.^[6]

Chemistry

Analogues

Analogues of EcPLA include MiPLA, LAMPA (MPLA), EPLA, EiPLA, ETFELA, and LSZ, among others.^[5]^[3]^[2]

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.^[3] It was developed by Lizard Labs.^{[citation needed]} The drug was encountered online as a novel designer drug in around 2020 and became more widely available in early 2022.^[4]

References

↑ "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.
1 2 3 Kavanagh PV, Westphal F, Stratford A, Elliott SP, Dowling G, Halberstadt AL, et al. (2020). "Analytical profile of N-ethyl-N-cyclopropyl lysergamide (ECPLA), an isomer of lysergic acid 2,4-dimethylazetidide (LSZ)". Drug Testing and Analysis. 12 (10): 1514–1521. doi:10.1002/dta.2911. ISSN 1942-7611. PMC 9191644. PMID 32803833.
1 2 3 4 5 6 Halberstadt AL, Klein LM, Chatha M, Valenzuela LB, Stratford A, Wallach J, et al. (February 2019). "Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA)". Psychopharmacology. 236 (2): 799–808. doi:10.1007/s00213-018-5117-z. PMC 6848745. PMID 30298278.
1 2 3 4 5 "ECPLA". АИПСИН (in Russian). Retrieved 1 January 2026.
1 2 Wachełko O, Nowak K, Tusiewicz K, Zawadzki M, Szpot P (January 2025). "A highly sensitive UHPLC-MS/MS method for determining 15 designer LSD analogs in biological samples with application to stability studies". Analyst. 150 (2): 290–308. doi:10.1039/d4an01361a. PMID 39636448.
↑ Wagmann L, Richter LH, Kehl T, Wack F, Bergstrand MP, Brandt SD, et al. (July 2019). "In vitro metabolic fate of nine LSD-based new psychoactive substances and their analytical detectability in different urinary screening procedures" (PDF). Analytical and Bioanalytical Chemistry. 411 (19): 4751–4763. doi:10.1007/s00216-018-1558-9. PMID 30617391. S2CID 58615418.

External links

ECPLA - Isomer Design

[1] "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.

[KavanaghWestphalStratford2020-2] 1 2 3 Kavanagh PV, Westphal F, Stratford A, Elliott SP, Dowling G, Halberstadt AL, et al. (2020). "Analytical profile of N-ethyl-N-cyclopropyl lysergamide (ECPLA), an isomer of lysergic acid 2,4-dimethylazetidide (LSZ)". Drug Testing and Analysis. 12 (10): 1514–1521. doi:10.1002/dta.2911. ISSN 1942-7611. PMC 9191644. PMID 32803833.

[HalberstadtKleinChatha2019-3] 1 2 3 4 5 6 Halberstadt AL, Klein LM, Chatha M, Valenzuela LB, Stratford A, Wallach J, et al. (February 2019). "Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA)". Psychopharmacology. 236 (2): 799–808. doi:10.1007/s00213-018-5117-z. PMC 6848745. PMID 30298278.

[Aipsin-4] 1 2 3 4 5 "ECPLA". АИПСИН (in Russian). Retrieved 1 January 2026.

[WachełkoNowakTusiewicz2025-5] 1 2 Wachełko O, Nowak K, Tusiewicz K, Zawadzki M, Szpot P (January 2025). "A highly sensitive UHPLC-MS/MS method for determining 15 designer LSD analogs in biological samples with application to stability studies". Analyst. 150 (2): 290–308. doi:10.1039/d4an01361a. PMID 39636448.

[WagmannRichterKehl2019-6] Wagmann L, Richter LH, Kehl T, Wack F, Bergstrand MP, Brandt SD, et al. (July 2019). "In vitro metabolic fate of nine LSD-based new psychoactive substances and their analytical detectability in different urinary screening procedures" (PDF). Analytical and Bioanalytical Chemistry. 411 (19): 4751–4763. doi:10.1007/s00216-018-1558-9. PMID 30617391. S2CID 58615418.

[2]

[3]

[4]

[5]

[1]

[6]