13-Hydroxy-LSD

13-Hydroxy-LSD is a lysergamide and a metabolite of the psychedelic drug lysergic acid diethylamide (LSD).^[1][2][3][4] It is a major metabolite of LSD in rats and guinea pigs but a minor metabolite of LSD in monkeys and humans.^[1][4] Following its formation, 13-hydroxy-LSD undergoes further metabolism via glucuronidation.^[1][2][3][4] Little is known about the specific enzymes responsible for generation of LSD metabolites such as 13-hydroxy-LSD in humans.^[3][5]

13-Hydroxy-LSD

Clinical data
Other names	13-Hydroxylysergic acid diethylamide; 13-OH-LSD; N,N-Diethyl-13-hydroxy-6-methyl-9,10-didehydroergoline-8β-carboxamide
ATC code	None
Identifiers
IUPAC name (6aR,9R)-N,N-diethyl-2-hydroxy-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
PubChem CID	56634866
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=CC(=CC(=C34)C2=C1)O)C
InChI InChI=1S/C20H25N3O2/c1-4-23(5-2)20(25)13-6-15-16-8-14(24)9-17-19(16)12(10-21-17)7-18(15)22(3)11-13/h6,8-10,13,18,21,24H,4-5,7,11H2,1-3H3/t13-,18-/m1/s1 Key:DZJOIBRTROBFRQ-FZKQIMNGSA-N

According to David E. Nichols in 2016, the pharmacology of hydroxylated metabolites of LSD like 13-hydroxy-LSD has not been studied.^[6] Nichols has posited that metabolism of LSD into active metabolites with potent dopamine receptor activity may be responsible for the delayed-onset dopaminergic stimulus effects of LSD in rodent drug discrimination tests.^[6][7][8] Relatedly, lergotrile's corresponding metabolite 13-hydroxylergotrile is several-fold more potent as a dopamine receptor agonist than lergotrile itself in vitro.^[6][9] However, more research is needed to assess the activity of 13-hydroxy-LSD and its potential involvement in LSD's effects.^[6] In any case, metabolites of LSD, possibly including 13-hydroxy-LSD, have been reported to be pharmacologically active with LSD-like effects in animals, although details do not appear to have been provided.^[10][4]

The 13 position of the ergoline ring system as in LSD and 13-hydroxy-LSD corresponds to the 6 position of the indole ring as in simple tryptamines.^[11] 6-Hydroxy-DMT has been found to be active but less potent than dimethyltryptamine (DMT) in animals and to be inactive in humans at the assessed doses.^{[12][13][14][15][16]} Similarly, it showed very low affinity for the serotonin 5-HT₂ receptors.^[17]

13-Hydroxy-LSD was first described in the scientific literature by at least 1963.^[18][11]

See also

• Substituted lysergamide
• 12-Hydroxy-LSD
• 6-Hydroxy-DMT