Ethylisopropyllysergamide

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).^[1][2][3] It is an isomer of ETH-LAD.^[3]

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

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

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

Chemistry

Analogues

Analogues of EiPLA include MiPLA, LAMPA (MPLA), EPLA, EcPLA, and ETFELA, among others.

History

EiPLA was first described in the scientific literature by David E. Nichols and colleagues by at least 1994.^[1] It appears to have emerged as a novel designer drug by 2019.^[3]

See also

• Substituted lysergamide
• Lizard Labs