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2-Oxo-3-hydroxy-LSD

Column 1
2-Oxy-3-hydroxy-LSD; OH-LSD; O-H-LSD; 2-Oxo-3-OH-LSD; 2-Oxo-3-hydroxy-2,3-dihydro-LSD; 2-Oxo-3-hydroxylysergide; 2-Oxo-3-hydroxylysergic acid diethylamide; N,N-Diethyl-2,3-dihydro-2-oxo-3-hydroxylysergamide; N,N-Diethyl-3-hydroxy-6-methyl-2-oxo-9,10-didehydro-2,3-dihydroergoline-8β-carboxamide
Serotonin receptor modulator
.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}None
IUPAC name
(6aR,9R)-N,N-diethyl-5a-hydroxy-7-methyl-5-oxo-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
111295-09-1
10155149
8330657
KU55DR6345
DTXSID00436244
C20H25N3O3
355.438 g·mol−1
Interactive image
SMILES
CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3(C4=C(C2=C1)C=CC=C4NC3=O)O)C
InChI
InChI=1S/C20H25N3O3/c1-4-23(5-2)18(24)12-9-14-13-7-6-8-15-17(13)20(26,19(25)21-15)10-16(14)22(3)11-12/h6-9,12,16,26H,4-5,10-11H2,1-3H3,(H,21,25)/t12-,16-,20?/m1/s1Key:YSZSHHCNLVHCNV-VRORWYBRSA-N

2-Oxo-3-hydroxy-LSD, or 2-oxy-3-hydroxy-LSD, also known as O-H-LSD or OH-LSD, as well as more fully as 2-oxo-3-hydroxy-2,3-dihydro-LSD, is a lysergamide and the major metabolite of the psychedelic drug lysergic acid diethylamide (LSD). LSD is eliminated 13% as O-H-LSD in urine within 24 hours and urinary concentrations of O-H-LSD are 4 to 40 times those of LSD in humans.

The specific enzymes responsible for the formation of O-H-LSD from LSD are unclear. However, subsequent research found involvement of several cytochrome P450 enzymes. O-H-LSD is thought to form from other LSD metabolites like 2-oxo-LSD and 3-hydroxy-LSD.

It is unknown whether O-H-LSD is pharmacologically active or produces hallucinogenic effects. However, O-H-LSD showed profoundly reduced albeit still detectable activity at the serotonin 5-HT2 receptors, including the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors, compared to LSD in vitro.

O-H-LSD was first described in the scientific literature by at least the 1990s. It started being sold online as an analytical standard by 2024.

  • Substituted lysergamide

  • 2-Oxo-LSD

  • 2,3-Dihydro-LSD

  • Nor-LSD

  • Lysergic acid ethyl-2-hydroxyethylamide (LEO)

  • Lysergic acid ethylamide (LAE)

  • 13-Hydroxy-LSD

  • 14-Hydroxy-LSD

  • OH-LSD - Isomer Design

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