Ethylpropyllysergamide

EPLA
Clinical data
Other names	N-Ethyl-N-propyllysergamide; Ethylpropyllysergamide; EPLA; Lysergic acid ethylpropylamide; LEP; LEP-57; N-Ethyl-6-methyl-N-propyl-9,10-didehydroergoline-8β-carboxamide
Drug class	Serotonergic psychedelic; Hallucinogen
Identifiers
	IUPAC name (6aR,9R)-N-ethyl-7-methyl-N-propyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide;
PubChem CID	166935919;
Chemical and physical data
Formula	C21H27N3O
Molar mass	337.467 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCN(C(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)CC;
	InChI InChI=1S/C21H27N3O/c1-4-9-24(5-2)21(25)15-10-17-16-7-6-8-18-20(16)14(12-22-18)11-19(17)23(3)13-15/h6-8,10,12,15,19,22H,4-5,9,11,13H2,1-3H3/t15-,19-/m1/s1; Key:LRVSYILBFXYJOP-DNVCBOLYSA-N;

N-Ethyl-N-propyllysergamide (EPLA), also known as lysergic acid ethylpropylamide (LEP or LEP-57), is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD).^[1]^[2]^[3]^[4]^[5]^[6] It is the analogue of LSD in which the amide group has one ethyl group and one propyl group instead of two ethyl groups.^[1]^[2]^[3]^[4]^[5]^[6]

Quick Facts Clinical data, Other names ...

The drug shows affinity for serotonin receptors and acts as a serotonin 5-HT_2A receptor agonist similarly to LSD.^[1] EPLA has about one-third of the potency of LSD in producing psychedelic effects in humans.^[4]^[2]^[3]^[6] Its exact dosage has not been reported.^[5]

EPLA was first described in the scientific literature by at least 1959.^[7]^[8] It was reportedly encountered as a designer drug by the 1990s.^[9]

See also