12-Hydroxy-LSD

12-Hydroxy-LSD
Clinical data
Other names	12-Hydroxylysergic acid diethylamide; 12-OH-LSD; 12-HO-LSD; "5-OH-LSD"; "5-HO-LSD"; "5-Hydroxy-LSD"; 9,10-Didehydro-N,N-diethyl-6-methyl-12-hydroxyergoline-8β-carboxamide
Drug class	Serotonin receptor modulator
Identifiers
	IUPAC name (6aR,9R)-N,N-diethyl-1-hydroxy-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;
CAS Number	60573-89-9;
PubChem CID	3042820;
ChemSpider	2305940;
CompTox Dashboard (EPA)	DTXSID00209374 ;
Chemical and physical data
Formula	C20H25N3O2
Molar mass	339.439 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=C3C(=C(C=C4)O)C2=C1)C;
	InChI InChI=1S/C20H25N3O2/c1-4-23(5-2)20(25)13-8-14-16(22(3)11-13)9-12-10-21-15-6-7-17(24)19(14)18(12)15/h6-8,10,13,16,21,24H,4-5,9,11H2,1-3H3/t13-,16-/m1/s1; Key:SJBIVHSZSSHVGK-CZUORRHYSA-N;

12-Hydroxy-LSD is a drug of the ergoline and lysergamide families and a derivative of lysergic acid diethylamide (LSD). In terms of chemical structure, 12-hydroxy-LSD is to LSD as bufotenin (5-HO-DMT) is to dimethyltryptamine (DMT), with 12-hydroxy-LSD notably containing bufotenin within its rigidified structure. 12-Hydroxy-LSD produces psychedelic-like effects in animals, whereas reports on its activities in humans are very limited and have been conflicting.