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14-Hydroxy-LSD

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

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Jun 6, 2026
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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
  • (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)
  • CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=C(C=CC(=C34)C2=C1)O)C
  • 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).123456 It is formed via aromatic hydroxylation at position 14 of the lysergic acid moiety and is subsequently excreted as a glucuronide conjugate.1236

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.12758910 In contrast, it appears only as a minor metabolite in rhesus monkeys and humans.127589 Studies using human liver microsomes and urine samples have confirmed its presence in humans, but in low concentrations that are often below quantification limits.736

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 1975.1121314

See also

See also

References

References

  1. Nichols DE (October 2018). "Dark Classics in Chemical Neuroscience: Lysergic Acid Diethylamide (LSD)" (PDF). ACS Chemical Neuroscience. 9 (10): 2331–2343. doi:10.1021/acschemneuro.8b00043. PMID 29461039. In animals, metabolism of LSD is highly species dependent...
  2. Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A (2008). "The pharmacology of lysergic acid diethylamide: a review". CNS Neuroscience & Therapeutics. 14 (4): 295–314. doi:10.1111/j.1755-5949.2008.00059.x. PMC 6494066. PMID 19040555. The metabolism of [14C]-LSD has been investigated...
  3. Libânio Osório Marta RF (August 2019). "Metabolism of lysergic acid diethylamide (LSD): an update". Drug Metabolism Reviews. 51 (3): 378–387. doi:10.1080/03602532.2019.1638931. PMID 31266388. Furthermore, it seems to occur an aromatic hydroxylation...
  4. Barceloux DG (9 March 2012). Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants. Wiley. pp. 452–466. doi:10.1002/9781118105955.ch22. ISBN 978-0-471-72760-6. There are limited data on the metabolites of LSD in humans...
  5. Meyer MR, Maurer HH (18 April 2012). "Drugs of Abuse (Including Designer Drugs)". Metabolism of Drugs and Other Xenobiotics. Wiley. pp. 429–463. doi:10.1002/9783527630905.ch16. ISBN 978-3-527-32903-8. Retrieved 30 June 2025. It is metabolized to the following five metabolites...
  6. Luethi D, Hoener MC, Krähenbühl S, Liechti ME, Duthaler U (June 2019). "Cytochrome P450 enzymes contribute to the metabolism of LSD to nor-LSD and 2-oxo-3-hydroxy-LSD: Implications for clinical LSD use". Biochemical Pharmacology. 164: 129–138. doi:10.1016/j.bcp.2019.04.013. PMID 30981875. LSD is rapidly metabolized in humans...
  7. Dolder P (2017). The Pharmacology of d-Lysergic Acid Diethylamide (LSD) (PDF) (Thesis). University of Basel. doi:10.5451/UNIBAS-006786123. In rodents, the major metabolites...
  8. Yu AM (June 2008). "Indolealkylamines: biotransformations and potential drug-drug interactions". The AAPS Journal. 10 (2) 242: 242–253. doi:10.1208/s12248-008-9028-5. PMC 2751378. PMID 18454322. LSD is extensively metabolized in laboratory animals...
  9. Araújo AM, Carvalho F, Bastos Mde L, Guedes de Pinho P, Carvalho M (August 2015). "The hallucinogenic world of tryptamines: an updated review" (PDF). Archives of Toxicology. 89 (8): 1151–1173. Bibcode:2015ArTox..89.1151A. doi:10.1007/s00204-015-1513-x. PMID 25877327. Major metabolites detected in the rat and guinea pigs urine...
  10. Siddik ZH, Barnes RD, Dring LG, Smith RL, Williams RT (October 1979). "The fate of lysergic acid DI[14C]ethylamide ([14C]LSD) in the rat, guinea pig and rhesus monkey and of [14C]iso-LSD in rat". Biochemical Pharmacology. 28 (20): 3093–3101. doi:10.1016/0006-2952(79)90618-x. PMID 117811. EEG studies...
  11. Nichols DE (April 2016). Barker EL (ed.). "Psychedelics". Pharmacological Reviews. 68 (2): 264–355. doi:10.1124/pr.115.011478. ISSN 0031-6997. PMC 4813425. PMID 26841800. [...] It also seems possible that one of the metabolites of LSD...
  12. Siddik ZH, Barnes RD, Dring LG, Smith RL, Williams RT (1975). "The Fate of Lysergic Acid Di[14C]ethylamide ([14C]LSD) in the Rat". Biochemical Society Transactions. 3 (2): 290–292. doi:10.1042/bst0030290. PMID 1132562.
  13. Sullivan AT, Twitchett PJ, Fletcher SM, Moffat AC (1978). "The fate of LSD in the body: forensic considerations". Journal - Forensic Science Society. 18 (1–2): 89–98. doi:10.1016/s0015-7368(78)71189-8. PMID 105081.
  14. Back DJ, Singh JK (May 1976). "The biliary excretion of [3H] lysergic acid diethylamide in Wistar and Gunn rats". Experientia. 32 (5): 616–617. doi:10.1007/BF01990195. PMID 1278313.
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