# 14-Hydroxy-LSD > Mediated Wiki article. Canonical URL: https://mediated.wiki/source/14-Hydroxy-LSD > Markdown URL: https://mediated.wiki/source/14-Hydroxy-LSD.md > Source: https://en.wikipedia.org/wiki/14-Hydroxy-LSD > Source revision: 1353893509 > License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/) **14-Hydroxy-LSD** is a [lysergamide](/source/Substituted_lysergamide) and a [metabolite](/source/Metabolite) of the [psychedelic drug](/source/Psychedelic_drug) [lysergic acid diethylamide](/source/Lysergic_acid_diethylamide) (LSD).[1][2][3][4][5][6] It is formed via [aromatic](/source/Aromatic_compound) [hydroxylation](/source/Hydroxylation) at position 14 of the lysergic acid [moiety](/source/Moiety_(chemistry)) and is subsequently [excreted](/source/Excretion) as a [glucuronide](/source/Glucuronide) [conjugate](/source/Conjugation_(biochemistry)).[1][2][3][6] 14-Hydroxy-LSD is a major [metabolite](/source/Metabolite) of LSD in rats and guinea pigs, where it is excreted predominantly as a glucuronide in [bile](/source/Bile) and [urine](/source/Urine).[1][2][7][5][8][9][10] In contrast, it appears only as a minor metabolite in [rhesus monkeys](/source/Rhesus_monkey) and humans.[1][2][7][5][8][9] Studies using human [liver](/source/Liver) [microsomes](/source/Microsome) 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](/source/Enzyme) involved in the formation of hydroxylated LSD metabolites like 14-hydroxy-LSD remain unidentified.[5] As of 2016, [David E. Nichols](/source/David_E._Nichols) noted that the [pharmacology](/source/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](/source/Electroencephalogram) of rabbits, in contrast to LSD and [13-hydroxy-LSD](/source/13-hydroxy-LSD).[10] 14-Hydroxy-LSD was first reported in the [scientific literature](/source/Scientific_literature) by at least 1975.[1][12][13][14] ## See also - [Substituted lysergamide](/source/Substituted_lysergamide) - [14-Methoxy-LSD](/source/14-Methoxy-LSD) - [14-Methyl-LSD](/source/14-Methyl-LSD) - [12-Hydroxy-LSD](/source/12-Hydroxy-LSD) - [13-Hydroxy-LSD](/source/13-Hydroxy-LSD) - [2-Oxo-LSD](/source/2-Oxo-LSD) - [2-Oxo-3-hydroxy-LSD](/source/2-Oxo-3-hydroxy-LSD) ## References 1. Nichols DE (October 2018). ["Dark Classics in Chemical Neuroscience: Lysergic Acid Diethylamide (LSD)"](https://shaunlacob.com/wp-content/uploads/2020/12/DC-LSD.pdf). *ACS Chemical Neuroscience*. **9** (10): 2331–2343. [doi:10.1021/acschemneuro.8b00043](https://doi.org/10.1021/acschemneuro.8b00043). [PMID 29461039](https://pubmed.ncbi.nlm.nih.gov/29461039) In animals, metabolism of LSD is highly species dependent... 1. 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](https://doi.org/10.1111/j.1755-5949.2008.00059.x). [PMC 6494066](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6494066). [PMID 19040555](https://pubmed.ncbi.nlm.nih.gov/19040555) The metabolism of [14C]-LSD has been investigated... 1. 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](https://doi.org/10.1080/03602532.2019.1638931). [PMID 31266388](https://pubmed.ncbi.nlm.nih.gov/31266388) Furthermore, it seems to occur an aromatic hydroxylation... 1. Barceloux DG (9 March 2012). *Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants*. Wiley. pp. 452–466. [doi:10.1002/9781118105955.ch22](https://doi.org/10.1002/9781118105955.ch22). ISBN 978-0-471-72760-6. There are limited data on the metabolites of LSD in humans... 1. Meyer MR, Maurer HH (18 April 2012). ["Drugs of Abuse (Including Designer Drugs)"](https://onlinelibrary.wiley.com/doi/10.1002/9783527630905.ch16). *Metabolism of Drugs and Other Xenobiotics*. Wiley. pp. 429–463. [doi:10.1002/9783527630905.ch16](https://doi.org/10.1002/9783527630905.ch16). ISBN 978-3-527-32903-8. Retrieved 30 June 2025. It is metabolized to the following five metabolites... 1. 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](https://doi.org/10.1016/j.bcp.2019.04.013). [PMID 30981875](https://pubmed.ncbi.nlm.nih.gov/30981875) LSD is rapidly metabolized in humans... 1. Dolder P (2017). [*The Pharmacology of d-Lysergic Acid Diethylamide (LSD)*](https://core.ac.uk/download/pdf/154350706.pdf). University of Basel. [doi:10.5451/UNIBAS-006786123](https://doi.org/10.5451/UNIBAS-006786123) In rodents, the major metabolites... 1. 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](https://doi.org/10.1208/s12248-008-9028-5). [PMC 2751378](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2751378). [PMID 18454322](https://pubmed.ncbi.nlm.nih.gov/18454322) LSD is extensively metabolized in laboratory animals... 1. Araújo AM, Carvalho F, Bastos Mde L, Guedes de Pinho P, Carvalho M (August 2015). ["The hallucinogenic world of tryptamines: an updated review"](https://psilosybiini.info/paperit/The%20hallucinogenic%20world%20of%20tryptamines,%20an%20updated%20review%20(Ara%FAjo%20et%20al.,%202015).pdf). *Archives of Toxicology*. **89** (8): 1151–1173. [Bibcode:2015ArTox..89.1151A](https://ui.adsabs.harvard.edu/abs/2015ArTox..89.1151A). [doi:10.1007/s00204-015-1513-x](https://doi.org/10.1007/s00204-015-1513-x). [PMID 25877327](https://pubmed.ncbi.nlm.nih.gov/25877327) Major metabolites detected in the rat and guinea pigs urine... 1. 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](https://doi.org/10.1016/0006-2952(79)90618-x). [PMID 117811](https://pubmed.ncbi.nlm.nih.gov/117811) EEG studies... 1. Nichols DE (April 2016). "Psychedelics". *Pharmacological Reviews*. **68** (2): 264–355. [doi:10.1124/pr.115.011478](https://doi.org/10.1124/pr.115.011478). [ISSN 0031-6997](https://www.worldcat.org/issn/0031-6997). [PMC 4813425](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4813425). [PMID 26841800](https://pubmed.ncbi.nlm.nih.gov/26841800) [...] It also seems possible that one of the metabolites of LSD... 1. 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](https://doi.org/10.1042/bst0030290). [PMID 1132562](https://pubmed.ncbi.nlm.nih.gov/1132562) 1. 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](https://doi.org/10.1016/s0015-7368(78)71189-8). [PMID 105081](https://pubmed.ncbi.nlm.nih.gov/105081) 1. 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](https://doi.org/10.1007/BF01990195). [PMID 1278313](https://pubmed.ncbi.nlm.nih.gov/1278313) ## External links - [14-OH-LSD - Isomer Design](https://isomerdesign.com/pihkal/explore/9728) --- Adapted from the Wikipedia article [14-Hydroxy-LSD](https://en.wikipedia.org/wiki/14-Hydroxy-LSD) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/14-Hydroxy-LSD?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.