LSD

Lysergic acid diethylamide
INN: Lysergide
Clinical data
Pronunciation/daɪ eθəl ˈæmaɪd/, /æmɪd/, or /eɪmaɪd/[1][2][3]
Other namesLSD; LSD-25; LAD; Acid; Lucy; Lysergide; d-LSD; (+)-LSD; (5R,8R)-LSD; 9,10-Didehydro-N,N-diethyl-6-methylergoline-8β-carboxamide; N,N-Diethyl-d-lysergamide; d-Lysergic acid diethylamide; METH-LAD; EA-1729
AHFS/Drugs.comReference
Pregnancy
category
  • C
Dependence
liability
Low[4]
Addiction
liability
None[5]
Routes of
administration
By mouth, sublingual
Drug classSerotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Bioavailability80%[6][7]
Protein bindingUnknown[8]
MetabolismLiver (CYP450)[9]
Metabolites• 2-Oxo-3-hydroxy-LSD[9][10]
• 2-Oxo-LSD[10]
LAETooltip Lysergic acid ethylamide[10]
LEOTooltip Lysergic acid ethyl-2-hydroxyethylamide[10]
Nor-LSD[10]
13-Hydroxy-LSD[10]
• 14-Hydroxy-LSD[10]
Glucuronides[10]
Onset of actionOral: 0.4–1.0 (range 0.1–1.8) hours[11][8]
IMTooltip Intramuscular injection: 15–20 min[8]
IVTooltip Intravenous injection: 2.5 min[6]
ITTooltip Intrathecal injection: <1 min[8][12]
Elimination half-life3.6 hours[9][13]
Duration of actionOral: 7–12 (range 4–22) hours[11][8]
IMTooltip Intramuscular injection, IVTooltip Intravenous injection, ITTooltip Intrathecal injection: 8–10 hours[8][6]
ExcretionKidneys[9][13]
Identifiers
  • (6aR,9R)-N,N-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.031 Edit this at Wikidata
Chemical and physical data
FormulaC20H25N3O
Molar mass323.440 g·mol−1
3D model (JSmol)
Melting point80 to 85 °C (176 to 185 °F)
Solubility in water67.02[14] mg/mL (20 °C)
  • CCN(CC)C(=O)[C@H]1CN([C@@H]2Cc3c[nH]c4c3c(ccc4)C2=C1)C
  • InChI=1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3/t14-,18-/m1/s1 checkY
  • Key:VAYOSLLFUXYJDT-RDTXWAMCSA-N checkY
  (verify)

Lysergic acid diethylamide, commonly known as LSD (from German Lysergsäure-diethylamid; often referred to as acid or lucy), is a semisynthetic, hallucinogenic compound derived from ergot, known for its powerful psychological effects and serotonergic activity.[15] It was historically significant in psychiatry and 1960s counterculture; it is currently legally restricted but experiencing renewed scientific interest and increasing use.

When taken orally, LSD has an onset of action within 0.4 to 1.0 hours (range: 0.1–1.8 hours) and a duration of effect lasting 7 to 12 hours (range: 4–22 hours).[11][8] It is commonly administered via tabs of blotter paper.[16] LSD is extremely potent, with noticeable effects at doses as low as 20 micrograms and is sometimes taken in much smaller amounts for microdosing. Yet no fatal human overdoses have been documented. LSD is mainly used recreationally or for spiritual purposes.[17][18] LSD can cause mystical experiences.[19][20] LSD exerts its effects primarily through high-affinity binding to several serotonin receptors, especially 5-HT2A, and to a lesser extent dopaminergic and adrenergic receptors. LSD reduces oscillatory power in the brain's default mode network and flattens brain hierarchy.[21][22] At higher doses, it can induce visual and auditory hallucinations, ego dissolution, and anxiety.[23][24] LSD use can cause adverse psychological effects such as paranoia and delusions and may lead to persistent visual disturbances known as hallucinogen persisting perception disorder (HPPD).

Swiss chemist Albert Hofmann first synthesized LSD in 1938 and discovered its powerful psychedelic effects in 1943 after accidental ingestion. It became widely studied in the 1950s and 1960s.[17][25] It was initially explored for psychiatric use due to its structural similarity to serotonin and safety profile.[26] It was used experimentally in psychiatry for treating alcoholism and schizophrenia.[27] By the mid-1960s, LSD became central to the youth counterculture in places like San Francisco and London, influencing art, music, and social movements through events like Acid Tests and figures such as Owsley Stanley and Michael Hollingshead. Its psychedelic effects inspired distinct visual art styles, music innovations, and caused a lasting cultural impact. However, its association with the counterculture movement of the 1960s led to its classification as a Schedule I drug in the U.S. in 1968.[28] It was also listed as a Schedule I controlled substance by the United Nations in 1971 and remains without approved medical uses.[17]

Despite its legal restrictions, LSD remains influential in scientific and cultural contexts. Research on LSD declined due to cultural controversies by the 1960s, but has resurged since 2009. In 2024, the U.S. Food and Drug Administration designated a form of LSD a breakthrough therapy for generalized anxiety disorder. As of 2017, about 10% of people in the U.S. had used LSD at some point, with 0.7% having used it in the past year.[29] Usage rates have risen, with a 56.4% increase in adult use in the U.S. from 2015 to 2018.[30]

  1. ^ "Definition of "amide"". Collins English Dictionary. Archived from the original on April 2, 2015. Retrieved January 31, 2015.
  2. ^ "American Heritage Dictionary Entry: amide". Ahdictionary.com. Archived from the original on April 2, 2015. Retrieved January 31, 2015.
  3. ^ "amide – definition of amide in English from the Oxford Dictionary". Oxforddictionaries.com. Archived from the original on April 2, 2015. Retrieved January 31, 2015.
  4. ^ Halpern JH, Suzuki J, Huertas PE, Passie T (June 7, 2014). "Hallucinogen Abuse and Dependence". In Price LH, Stolerman IP (eds.). Encyclopedia of Psychopharmacology A Springer Live Reference. Heidelberg, Germany: Springer-Verlag Berlin Heidelberg. pp. 1–5. doi:10.1007/978-3-642-27772-6_43-2. ISBN 978-3-642-27772-6. Hallucinogen abuse and dependence are known complications resulting from ... LSD and psilocybin. Users do not experience withdrawal symptoms, but the general criteria for substance abuse and dependence otherwise apply. Dependence is estimated in approximately 2 % of recent-onset users
  5. ^ Cite error: The named reference NHM-MDMA was invoked but never defined (see the help page).
  6. ^ a b c Arikci D, Holze F, Mueller L, Vizeli P, Rudin D, Luethi D, et al. (May 2025). "Absolute Oral Bioavailability and Bioequivalence of LSD Base and Tartrate in a Double-Blind, Placebo-Controlled, Crossover Study". Clin Pharmacol Ther. doi:10.1002/cpt.3726. PMID 40418105.
  7. ^ Holze F, Mueller L, Vizeli P, Luethi D, Rudin D, Hysek C, et al. (2024). "Oral LSD base and tartrate bioequivalence and absolute bioavailability in healthy participants". Neuroscience Applied. 3: 105132. doi:10.1016/j.nsa.2024.105132.
  8. ^ a b c d e f g Cite error: The named reference PassieHalpernStrichtenoth2008 was invoked but never defined (see the help page).
  9. ^ a b c d Dolder PC, Schmid Y, Haschke M, Rentsch KM, Liechti ME (June 2015). "Pharmacokinetics and Concentration-Effect Relationship of Oral LSD in Humans". The International Journal of Neuropsychopharmacology. 19 (1): pyv072. doi:10.1093/ijnp/pyv072. PMC 4772267. PMID 26108222.
  10. ^ a b c d e f g h Cite error: The named reference Dolder2017 was invoked but never defined (see the help page).
  11. ^ a b c Cite error: The named reference HolzeSinghLiechti2024 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference Shulgin1980b was invoked but never defined (see the help page).
  13. ^ a b Cite error: The named reference Muc2016 was invoked but never defined (see the help page).
  14. ^ "Lysergide". pubchem.ncbi.nlm.nih.gov. Archived from the original on April 12, 2023. Retrieved April 12, 2023.
  15. ^ PubChem. "Lysergide". pubchem.ncbi.nlm.nih.gov. Retrieved May 22, 2025.
  16. ^ "What are hallucinogens?". National Institute of Drug Abuse. January 2016. Archived from the original on April 17, 2016. Retrieved April 24, 2016.
  17. ^ a b c "LSD profile (chemistry, effects, other names, synthesis, mode of use, pharmacology, medical use, control status)". EMCDDA. Archived from the original on April 28, 2021. Retrieved July 14, 2018.
  18. ^ Gershon L (July 19, 2016). "How LSD Went From Research to Religion". JSTOR Daily. Archived from the original on January 28, 2021. Retrieved July 14, 2018.
  19. ^ Liechti ME, Dolder PC, Schmid Y (May 2017). "Alterations of consciousness and mystical-type experiences after acute LSD in humans". Psychopharmacology. 234 (9–10): 1499–1510. doi:10.1007/s00213-016-4453-0. PMC 5420386. PMID 27714429.
  20. ^ Griffiths RR, Hurwitz ES, Davis AK, Johnson MW, Jesse R (April 23, 2019). "Survey of subjective "God encounter experiences": Comparisons among naturally occurring experiences and those occasioned by the classic psychedelics psilocybin, LSD, ayahuasca, or DMT". PLOS ONE. 14 (4): e0214377. Bibcode:2019PLoSO..1414377G. doi:10.1371/journal.pone.0214377. PMC 6478303. PMID 31013281.
  21. ^ 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.
  22. ^ Girn M, Roseman L, Bernhardt B, Smallwood J, Carhart-Harris R, Spreng RN (May 3, 2020). "Serotonergic psychedelic drugs LSD and psilocybin reduce the hierarchical differentiation of unimodal and transmodal cortex". bioRxiv. doi:10.1101/2020.05.01.072314. S2CID 233346402.
  23. ^ Leptourgos P, Fortier-Davy M, Carhart-Harris R, Corlett PR, Dupuis D, Halberstadt AL, et al. (December 2020). "Hallucinations Under Psychedelics and in the Schizophrenia Spectrum: An Interdisciplinary and Multiscale Comparison". Schizophrenia Bulletin. 46 (6): 1396–1408. doi:10.1093/schbul/sbaa117. PMC 7707069. PMID 32944778.
  24. ^ Holze F, Vizeli P, Ley L, Müller F, Dolder P, Stocker M, et al. (February 2021). "Acute dose-dependent effects of lysergic acid diethylamide in a double-blind placebo-controlled study in healthy subjects". Neuropsychopharmacology. 46 (3): 537–544. doi:10.1038/s41386-020-00883-6. PMC 8027607. PMID 33059356.
  25. ^ "Commonly Abused Drugs Charts". National Institute on Drug Abuse. July 2, 2018. Archived from the original on March 1, 2020. Retrieved July 14, 2018.
  26. ^ 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.
  27. ^ Chwelos N, Blewett DB, Smith CM, Hoffer A (September 1959). "Use of d-lysergic acid diethylamide in the treatment of alcoholism". Quarterly Journal of Studies on Alcohol. 20 (3): 577–590. doi:10.15288/qjsa.1959.20.577. PMID 13810249.
  28. ^ United States Congress House Committee on Interstate and Foreign Commerce Subcommittee on Public Health and Welfare (1968). Increased Controls Over Hallucinogens and Other Dangerous Drugs. U.S. Government Printing Office. Archived from the original on July 13, 2020. Retrieved August 3, 2021.
  29. ^ National Institute on Drug Abuse. "Hallucinogens". Archived from the original on June 3, 2020. Retrieved July 14, 2018.
  30. ^ Yockey RA, Vidourek RA, King KA (July 2020). "Trends in LSD use among US adults: 2015–2018". Drug and Alcohol Dependence. 212: 108071. doi:10.1016/j.drugalcdep.2020.108071. PMID 32450479. S2CID 218893155.

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