EiPLA

EiPLA
Clinical data
Other names	EiPLA; Ethylisopropyllysergamide; N-Ethyl-N-isopropyllysergamide; Lysergic acid ethylisopropylamide
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;
Identifiers
	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;
CAS Number	154504-04-8;
PubChem CID	101661197;
Chemical and physical data
Formula	C21H27N3O
Molar mass	337.467 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(C(C)C)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C;
	InChI InChI=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; Key: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).^[2]^[3]^[1] It is an isomer of ETH-LAD.^[1]

Use and effects

EiPLA has been identified in blotter containing doses of 86 to 97 μg base equivalent per tab.^[1] Blotter containing 200 μg per tab has also been described.^[1] Anecdotal reports suggest that EiPLA produces psychedelic effects but is less potent than LSD.^[1]

Interactions

Pharmacology

Pharmacodynamics

In drug discrimination tests in rodents, EiPLA was found to have approximately half the potency of LSD.^[2]^[3]^[1]

Chemistry

Analogues

Analogues of EiPLA include MiPLA, LAMPA (MPLA), EPLA, EcPLA, and ETFELA, among others.^[1]^[4]

History

EiPLA was first described in the scientific literature by David E. Nichols and colleagues by at least 1994.^[2] It appears to have emerged as a novel designer drug by 2019.^[1]

References

1 2 3 4 5 6 7 8 9 Brandt SD, Kavanagh PV, Westphal F, Pulver B, Schwelm HM, Stratford A, et al. (February 2024). "Analytical and behavioral characterization of N-ethyl-N-isopropyllysergamide (EIPLA), an isomer of N6 -ethylnorlysergic acid N,N-diethylamide (ETH-LAD)". Drug Testing and Analysis. 16 (2): 187–198. doi:10.1002/dta.3530. PMID 37321559.
1 2 3 Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE (March 1994). "Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives". Pharmacology, Biochemistry, and Behavior. 47 (3): 667–673. doi:10.1016/0091-3057(94)90172-4. PMID 8208787.
1 2 Nichols DE (October 2018). "Dark Classics in Chemical Neuroscience: Lysergic Acid Diethylamide (LSD)". ACS Chemical Neuroscience. 9 (10): 2331–2343. doi:10.1021/acschemneuro.8b00043. PMID 29461039.
↑ 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.

External links

[BrandtKavanaghWestphal2024-1] 1 2 3 4 5 6 7 8 9 Brandt SD, Kavanagh PV, Westphal F, Pulver B, Schwelm HM, Stratford A, et al. (February 2024). "Analytical and behavioral characterization of N-ethyl-N-isopropyllysergamide (EIPLA), an isomer of N6 -ethylnorlysergic acid N,N-diethylamide (ETH-LAD)". Drug Testing and Analysis. 16 (2): 187–198. doi:10.1002/dta.3530. PMID 37321559.

[HuangMarona-LewickaPfaff1994-2] 1 2 3 Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE (March 1994). "Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives". Pharmacology, Biochemistry, and Behavior. 47 (3): 667–673. doi:10.1016/0091-3057(94)90172-4. PMID 8208787.

[Nichols2018-3] 1 2 Nichols DE (October 2018). "Dark Classics in Chemical Neuroscience: Lysergic Acid Diethylamide (LSD)". ACS Chemical Neuroscience. 9 (10): 2331–2343. doi:10.1021/acschemneuro.8b00043. PMID 29461039.

[WachełkoNowakTusiewicz2025-4] 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.

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