Lysergic acid ethyl-2-hydroxyethylamide

Lysergic acid ethyl-2-hydroxyethylamide
Clinical data
Other names	LEO; N-Ethyl-N-(2-hydroxyethyl)-6-methyl-9,10-didehydroergoline-8β-carboxamide
Drug class	Serotonin receptor modulator
ATC code	None;
Identifiers
	IUPAC name (6aR,9R)-N-ethyl-N-(2-hydroxyethyl)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;
CAS Number	65527-58-4;
PubChem CID	53938953;
ChemSpider	128919021;
Chemical and physical data
Formula	C20H25N3O2
Molar mass	339.439 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CCO)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C;
	InChI InChI=1S/C20H25N3O2/c1-3-23(7-8-24)20(25)14-9-16-15-5-4-6-17-19(15)13(11-21-17)10-18(16)22(2)12-14/h4-6,9,11,14,18,21,24H,3,7-8,10,12H2,1-2H3/t14-,18-/m1/s1; Key:IWLBOZQDDPXOIT-RDTXWAMCSA-N;

Lysergic acid ethyl-2-hydroxyethylamide (LEO) is a serotonin receptor modulator of the lysergamide family related to lysergic acid diethylamide (LSD). It is the derivative of LSD in which one of its N-ethyl groups of LSD has been hydroxylated at the end or 2 position. It is also an active metabolite of LSD including in humans. LEO shows potent antiserotonergic activity and oxytocic activity in the isolated rat uterus in vitro similarly to LSD. In addition, it produced hyperthermia in rabbits in vivo similarly to LSD. LEO was first described in the scientific literature by 1974.