Chemistry:14-Hydroxy-LSD

From HandWiki

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

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 "Dark Classics in Chemical Neuroscience: Lysergic Acid Diethylamide (LSD)". ACS Chemical Neuroscience 9 (10): 2331–2343. October 2018. doi:10.1021/acschemneuro.8b00043. PMID 29461039. https://shaunlacob.com/wp-content/uploads/2020/12/DC-LSD.pdf. "In animals, metabolism of LSD is highly species dependent...". 
  2. ↑ 2.0 2.1 2.2 2.3 "The pharmacology of lysergic acid diethylamide: a review". CNS Neuroscience & Therapeutics 14 (4): 295–314. 2008. doi:10.1111/j.1755-5949.2008.00059.x. PMID 19040555. "The metabolism of [14C]-LSD has been investigated...". 
  3. ↑ 3.0 3.1 3.2 "Metabolism of lysergic acid diethylamide (LSD): an update". Drug Metabolism Reviews 51 (3): 378–387. August 2019. doi:10.1080/03602532.2019.1638931. PMID 31266388. "Furthermore, it seems to occur an aromatic hydroxylation...". 
  4. ↑ Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants. Wiley. 9 March 2012. 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. ↑ 5.0 5.1 5.2 5.3 "Drugs of Abuse (Including Designer Drugs)". Metabolism of Drugs and Other Xenobiotics. Wiley. 18 April 2012. pp. 429–463. doi:10.1002/9783527630905.ch16. ISBN 978-3-527-32903-8. https://onlinelibrary.wiley.com/doi/10.1002/9783527630905.ch16. Retrieved 30 June 2025. "It is metabolized to the following five metabolites..." 
  6. ↑ 6.0 6.1 6.2 "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. June 2019. doi:10.1016/j.bcp.2019.04.013. PMID 30981875. "LSD is rapidly metabolized in humans...". 
  7. ↑ 7.0 7.1 7.2 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. ↑ 8.0 8.1 "Indolealkylamines: biotransformations and potential drug-drug interactions". The AAPS Journal 10 (2): 242–253. June 2008. doi:10.1208/s12248-008-9028-5. PMID 18454322. "LSD is extensively metabolized in laboratory animals...". 
  9. ↑ 9.0 9.1 "The hallucinogenic world of tryptamines: an updated review". Archives of Toxicology 89 (8): 1151–1173. August 2015. doi:10.1007/s00204-015-1513-x. PMID 25877327. Bibcode: 2015ArTox..89.1151A. https://psilosybiini.info/paperit/The%20hallucinogenic%20world%20of%20tryptamines,%20an%20updated%20review%20(Ara%FAjo%20et%20al.,%202015).pdf. "Major metabolites detected in the rat and guinea pigs urine...". 
  10. ↑ 10.0 10.1 "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. October 1979. doi:10.1016/0006-2952(79)90618-x. PMID 117811. "EEG studies...". 
  11. ↑ "Psychedelics". Pharmacological Reviews 68 (2): 264–355. April 2016. doi:10.1124/pr.115.011478. ISSN 0031-6997. PMID 26841800. "[...] It also seems possible that one of the metabolites of LSD...". 
  12. ↑ "The Fate of Lysergic Acid Di[14C]ethylamide ([14C]LSD) in the Rat". Biochemical Society Transactions 3 (2): 290–292. 1975. doi:10.1042/bst0030290. PMID 1132562. 
  13. ↑ "The fate of LSD in the body: forensic considerations". Journal - Forensic Science Society 18 (1–2): 89–98. 1978. doi:10.1016/s0015-7368(78)71189-8. PMID 105081. 
  14. ↑ "The biliary excretion of [3H] lysergic acid diethylamide in Wistar and Gunn rats". Experientia 32 (5): 616–617. May 1976. doi:10.1007/BF01990195. PMID 1278313. 



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