14-Hydroxy-LSD

14-Hydroxy-LSD
Clinical data
Other names14-Hydroxylysergic acid diethylamide; 14-OH-LSD; 14-HO-LSD; N,N-Diethyl-14-hydroxy-6-methyl-9,10-didehydroergoline-8β-carboxamide
ATC code
  • None
Identifiers
IUPAC name
  • (6aR,9R)-N,N-diethyl-3-hydroxy-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
PubChem CID
Chemical and physical data
FormulaC20H25N3O2
Molar mass339.439 g·mol−1
3D model (JSmol)
SMILES
  • CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=C(C=CC(=C34)C2=C1)O)C
InChI
  • InChI=1S/C20H25N3O2/c1-4-23(5-2)20(25)13-8-15-14-6-7-17(24)19-18(14)12(10-21-19)9-16(15)22(3)11-13/h6-8,10,13,16,21,24H,4-5,9,11H2,1-3H3/t13-,16-/m1/s1
  • Key:LAJBWPLMZBFOHF-CZUORRHYSA-N

14-Hydroxy-LSD is a lysergamide and a metabolite of the psychedelic drug lysergic acid diethylamide (LSD).[1][2][3][4][5][6] It is formed via aromatic hydroxylation at position 14 of the lysergic acid moiety and is subsequently excreted as a glucuronide conjugate.[1][2][3][6]

14-Hydroxy-LSD is a major metabolite of LSD in rats and guinea pigs, where it is excreted predominantly as a glucuronide in bile and urine.[1][2][7][5][8][9][10] In contrast, it appears only as a minor metabolite in rhesus monkeys and humans.[1][2][7][5][8][9] Studies using human liver microsomes and urine samples have confirmed its presence in humans, but in low concentrations that are often below quantification limits.[7][3][6]

The specific enzymes involved in the formation of hydroxylated LSD metabolites like 14-hydroxy-LSD remain unidentified.[5] As of 2016, David E. Nichols noted that the pharmacology of hydroxylated LSD metabolites, including 14-hydroxy-LSD, had not been studied.[11] Notably, 14-hydroxy-LSD does not induce LSD-like changes in the EEG of rabbits, in contrast to LSD and 13-hydroxy-LSD.[10]

14-Hydroxy-LSD was first reported in the scientific literature by at least 1975.[1][12][13][14]

  1. ^ a b c d e Cite error: The named reference Nichols_2018 was invoked but never defined (see the help page).
  2. ^ a b c d Cite error: The named reference Passie_2008 was invoked but never defined (see the help page).
  3. ^ a b c Cite error: The named reference Libanio_Osorio_Marta_2019 was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference Barceloux_2012 was invoked but never defined (see the help page).
  5. ^ a b c d Cite error: The named reference Meyer_2012 was invoked but never defined (see the help page).
  6. ^ a b c Cite error: The named reference Luethi_2019 was invoked but never defined (see the help page).
  7. ^ a b c Cite error: The named reference Dolder_2017 was invoked but never defined (see the help page).
  8. ^ a b Cite error: The named reference Yu_2008 was invoked but never defined (see the help page).
  9. ^ a b Cite error: The named reference Araujo_2015 was invoked but never defined (see the help page).
  10. ^ a b Cite error: The named reference Siddik_1979 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference Nichols_2016 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference Siddik_1975 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference Sullivan_1978 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference Back_1976 was invoked but never defined (see the help page).
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