Ethylisopropyllysergamide

Ethylisopropyllysergamide
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	92851-69-3;
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;

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.^[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.
^ 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.
^ 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] 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.

[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.

[pmid37321559-3] 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.

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