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14-Hydroxy-LSD is a lysergamide and a metabolite of the psychedelic drug lysergic acid diethylamide (LSD).cite-ref-nichols-2018-1-0[1]cite-ref-passie-2008-2-0[2]cite-ref-libanio-osorio-marta-2019-3-0[3]cite-ref-barceloux-2012-4-0[4]cite-ref-meyer-2012-5-0[5]cite-ref-luethi-2019-6-0[6] It is formed via aromatic hydroxylation at position 14 of the lysergic acid moiety and is subsequently excreted as a glucuronide conjugate.cite-ref-nichols-2018-1-1[1]cite-ref-passie-2008-2-1[2]cite-ref-libanio-osorio-marta-2019-3-1[3]cite-ref-luethi-2019-6-1[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.cite-ref-nichols-2018-1-2[1]cite-ref-passie-2008-2-2[2]cite-ref-dolder-2017-7-0[7]cite-ref-meyer-2012-5-1[5]cite-ref-yu-2008-8-0[8]cite-ref-araujo-2015-9-0[9]cite-ref-siddik-1979-10-0[10] In contrast, it appears only as a minor metabolite in rhesus monkeys and humans.cite-ref-nichols-2018-1-3[1]cite-ref-passie-2008-2-3[2]cite-ref-dolder-2017-7-1[7]cite-ref-meyer-2012-5-2[5]cite-ref-yu-2008-8-1[8]cite-ref-araujo-2015-9-1[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.cite-ref-dolder-2017-7-2[7]cite-ref-libanio-osorio-marta-2019-3-2[3]cite-ref-luethi-2019-6-2[6]

The specific enzymes involved in the formation of hydroxylated LSD metabolites like 14-hydroxy-LSD remain unidentified.cite-ref-meyer-2012-5-3[5] As of 2016, David E. Nichols noted that the pharmacology of hydroxylated LSD metabolites, including 14-hydroxy-LSD, had not been studied.cite-ref-nichols-2016-11-0[11] Notably, 14-hydroxy-LSD does not induce LSD-like changes in the EEG of rabbits, in contrast to LSD and 13-hydroxy-LSD.cite-ref-siddik-1979-10-1[10]

14-Hydroxy-LSD was first reported in the scientific literature by at least 1975.cite-ref-nichols-2018-1-4[1]cite-ref-siddik-1975-12-0[12]cite-ref-sullivan-1978-13-0[13]cite-ref-back-1976-14-0[14]

• See also

• References

• External links

• Substituted lysergamide

• 12-Hydroxy-LSD

• 13-Hydroxy-LSD

• 14-Methoxy-LSD

• 2-Oxo-LSD

• 2-Oxo-3-hydroxy-LSD

cite-note-nichols-2018-11. ↑ citerefnichols2018Nichols 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...

cite-note-passie-2008-22. ↑ citerefpassiehalpernstichtenothemrich2008Passie 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...

cite-note-libanio-osorio-marta-2019-33. ↑ citereflib-nio-os-rio-marta2019Libânio 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...

cite-note-barceloux-2012-44. ↑ citerefbarceloux2012Barceloux 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...

cite-note-meyer-2012-55. ↑ citerefmeyermaurer2012Meyer 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...

cite-note-luethi-2019-66. ↑ citerefluethihoenerkr-henb-hlliechti2019Luethi 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...

cite-note-dolder-2017-77. ↑ citerefdolder2017Dolder 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...

cite-note-yu-2008-88. ↑ citerefyu2008Yu 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...

cite-note-araujo-2015-99. ↑ citerefara-jocarvalhobastos-mdeguedes-de-pinho2015Araújo 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...

cite-note-siddik-1979-1010. ↑ citerefsiddikbarnesdringsmith1979Siddik 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...

cite-note-nichols-2016-1111. ↑ citerefnichols2016Nichols 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...

cite-note-siddik-1975-1212. ↑ citerefsiddikbarnesdringsmith1975Siddik 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.

cite-note-sullivan-1978-1313. ↑ citerefsullivantwitchettfletchermoffat1978Sullivan 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.

cite-note-back-1976-1414. ↑ citerefbacksingh1976Back 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.

• 14-OH-LSD - Isomer Design