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14-Hydroxy-LSD

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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).[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]

See also

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References

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  1. ^ a b c d e 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. ^ a b c d 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. ^ a b c 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. ^ a b c d 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. ^ a b c 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. ^ a b c 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. ^ a b Yu AM (June 2008). "Indolealkylamines: biotransformations and potential drug-drug interactions". The AAPS Journal. 10 (2): 242–253. doi:10.1208/s12248-008-9028-5. PMC 2751378. PMID 18454322. LSD is extensively metabolized in laboratory animals...
  9. ^ a b 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. doi:10.1007/s00204-015-1513-x. PMID 25877327. Major metabolites detected in the rat and guinea pigs urine...
  10. ^ a b 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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