Global InformationLSD information
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| Pronunciation | /daɪ eθəl ˈæmaɪd/, /æmɪd/, or /eɪmaɪd/[1][2][3] |
| Trade names | Delysid |
| Other names | LSD, LSD-25, LAD, Acid, others |
| AHFS/Drugs.com | Reference |
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| Dependence liability | Low[4] |
| Addiction liability | None[5] |
| Routes of administration | By mouth, under the tongue |
| Drug class | Hallucinogen (psychedelic) |
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| Pharmacokinetic data | |
| Bioavailability | 71%[6] |
| Protein binding | Unknown[7] |
| Metabolism | Liver (CYP450)[6] |
| Metabolites | 2-Oxo-3-hydroxy-LSD[6] |
| Onset of action | 30–40 minutes[8] |
| Elimination half-life | 3.6 hours[6][9] |
| Duration of action | 8–20 hours[10] |
| Excretion | Kidneys[6][9] |
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| ECHA InfoCard | 100.000.031 |
| Chemical and physical data | |
| Formula | C20H25N3O |
| Molar mass | 323.440 g·mol−1 |
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| Melting point | 80 to 85 °C (176 to 185 °F) |
| Solubility in water | 67.02[11] mg/mL (20 °C) |
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Lysergic acid diethylamide, commonly known as LSD (from German Lysergsäure-diethylamid), and known colloquially as acid or lucy, is a potent psychedelic drug.[12] Effects typically include intensified thoughts, emotions, and sensory perception.[13] At sufficiently high dosages, LSD manifests primarily mental, visual, and auditory hallucinations.[14][15] Dilated pupils, increased blood pressure, and increased body temperature are typical.[16]
Effects typically begin within half an hour and can last for up to 20 hours (although on average, experiences last 8–12 hours).[16][17] LSD is also capable of causing mystical experiences and ego dissolution.[15][18] It is used mainly as a recreational drug or for spiritual reasons.[16][19] LSD is both the prototypical psychedelic and one of the "classical" psychedelics, being the psychedelic with the greatest scientific and cultural significance.[12] LSD is synthesized as a solid compound, typically in the form of a powder or a crystalline material. This solid LSD is then dissolved in a liquid solvent, such as ethanol or distilled water, to create a solution. The liquid serves as a carrier for the LSD, allowing for accurate dosage and administration onto small pieces of blotter paper called tabs. LSD is typically either swallowed or held under the tongue.[13] In pure form, LSD is clear or white in color, has no smell, and is crystalline.[13] It breaks down with exposure to ultraviolet light.[16]
LSD is pharmacologically considered to be non-addictive with a low potential for abuse. Adverse psychological reactions are possible, such as anxiety, paranoia, and delusions.[7] In rare cases, LSD can induce "flashbacks", known as hallucinogen persisting perception disorder, in which a person experiences apparent lasting or persistent visual hallucinations or perceptual distortions, such as visual snow and palinopsia.[20][21]
LSD is structurally related to substituted tryptamines, a class of compounds that includes psilocybin, the active compound found in psychedelic mushrooms. Thus, LSD shares some mechanisms of action and psychedelic effects with psilocybin and other tryptamines.[22][23][24]
The effects of LSD are thought to stem primarily from it being an agonist at the 5-HT2A serotonin receptor. While exactly how LSD exerts its effects by agonism at this receptor is not fully understood, corresponding increased glutamatergic neurotransmission and reduced default mode network activity are thought to be key mechanisms of action.[7][12][25][26][27] LSD also binds to dopamine D1 and D2 receptors, which is thought to contribute to reports of LSD being more stimulating than compounds such as psilocybin.[28][29]
Swiss chemist Albert Hofmann first synthesized LSD in 1938 from lysergic acid, a chemical derived from the hydrolysis of ergotamine, an alkaloid found in ergot, a fungus that infects grain.[16][20] LSD was the 25th of various lysergamides Hofmann synthesized from lysergic acid while trying to develop a new analeptic, hence the alternate name LSD-25. Hofmann discovered its effects in humans in 1943, after unintentionally ingesting an unknown amount, possibly absorbing it through his skin.[30][31][32] LSD was subject to exceptional interest within the field of psychiatry in the 1950s and early 1960s, with Sandoz distributing LSD to researchers under the trademark name Delysid in an attempt to find a marketable use for it.[31]
LSD-assisted psychotherapy was used in the 1950s and early 1960s by psychiatrists such as Humphry Osmond, who pioneered the application of LSD to the treatment of alcoholism, with promising results.[31][33][34][35] Osmond coined the term "psychedelic" (lit. mind manifesting) as a term for LSD and related hallucinogens, superseding the previously held "psychotomimetic" model in which LSD was believed to mimic schizophrenia. In contrast to schizophrenia, LSD can induce transcendent experiences, or mental states that transcend the experience of everyday consciousness, with lasting psychological benefit.[12][31] During this time, the Central Intelligence Agency (CIA) began using LSD in the research project Project MKUltra, which used psychoactive substances to aid interrogation. The CIA administered LSD to unwitting test subjects in order to observe how they would react, the most well-known example of this being Operation Midnight Climax.[31] LSD was one of several psychoactive substances evaluated by the U.S. Army Chemical Corps as possible non-lethal incapacitants in the Edgewood Arsenal human experiments.[31]
In the 1960s, LSD and other psychedelics were adopted by, and became synonymous with, the counterculture movement due to their perceived ability to expand consciousness. This resulted in LSD being viewed as a cultural threat to American values and the Vietnam war effort, and it was designated as a Schedule I (illegal for medical as well as recreational use) substance in 1968.[36] It was listed as a Schedule 1 controlled substance by the United Nations in 1971 and currently has no approved medical uses.[16] As of 2017[update], about 10% of people in the United States have used LSD at some point in their lives, while 0.7% have used it in the last year.[37] It was most popular in the 1960s to 1980s.[16] The use of LSD among US adults increased 56.4% from 2015 to 2018.[38]
- ^ "Definition of "amide"". Collins English Dictionary. Archived from the original on April 2, 2015. Retrieved January 31, 2015.
- ^ "American Heritage Dictionary Entry: amide". Ahdictionary.com. Archived from the original on April 2, 2015. Retrieved January 31, 2015.
- ^ "amide – definition of amide in English from the Oxford Dictionary". Oxforddictionaries.com. Archived from the original on April 2, 2015. Retrieved January 31, 2015.
- ^ 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
- ^ Cite error: The named reference
NHM-MDMAwas invoked but never defined (see the help page). - ^ a b c d e Cite error: The named reference
Dol2015was invoked but never defined (see the help page). - ^ a b c 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.
- ^ Neinstein LS (2008). Adolescent Health Care: A Practical Guide. Lippincott Williams & Wilkins. p. 931. ISBN 9780781792561. Archived from the original on December 26, 2018. Retrieved January 27, 2017.
- ^ a b Cite error: The named reference
Muc2016was invoked but never defined (see the help page). - ^ Kranzler HR, Ciraulo DA (April 2, 2007). Clinical Manual of Addiction Psychopharmacology. American Psychiatric Pub. p. 216. ISBN 9781585626632. Archived from the original on December 26, 2018. Retrieved January 27, 2017.
- ^ "Lysergide". pubchem.ncbi.nlm.nih.gov.
- ^ a b c d Nichols DE (April 2016). Barker EL (ed.). "Psychedelics". Pharmacological Reviews. 68 (2): 264–355. doi:10.1124/pr.115.011478. PMC 4813425. PMID 26841800.
- ^ a b c "What are hallucinogens?". National Institute of Drug Abuse. January 2016. Archived from the original on April 17, 2016. Retrieved April 24, 2016.
- ^ 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.
Thalamocortical connectivity was found altered in psychedelic states. Specifically, LSD was found to selectively increase effective connectivity from the thalamus to certain DMN areas, while other connections are attenuated. Furthermore, increased thalamic connectivity with the right fusiform gyrus and the anterior insula correlated with visual and auditory hallucinations (AH), respectively.
- ^ a b 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.
- ^ a b c d e f g "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.
- ^ Sloat S (January 27, 2017). "This is Why You Can't Escape an Hours-Long Acid Trip". Inverse. Archived from the original on June 11, 2021. Retrieved February 3, 2020.
- ^ 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.
- ^ 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.
- ^ a b "Commonly Abused Drugs Charts". National Institute on Drug Abuse. July 2, 2018. Archived from the original on March 1, 2020. Retrieved July 14, 2018.
- ^ Halpern JH, Lerner AG, Passie T (2018). A Review of Hallucinogen Persisting Perception Disorder (HPPD) and an Exploratory Study of Subjects Claiming Symptoms of HPPD. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 333–360. doi:10.1007/7854_2016_457. ISBN 978-3-662-55878-2. PMID 27822679.
- ^ Wong S, Yu AY, Fabiano N, Finkelstein O, Pasricha A, Jones BDM, et al. (August 2023). "Beyond Psilocybin: Reviewing the Therapeutic Potential of Other Serotonergic Psychedelics in Mental and Substance Use Disorders". Journal of Psychoactive Drugs: 1–17. doi:10.1080/02791072.2023.2251133. PMID 37615379. S2CID 261098164.
- ^ Walker SR, Pullella GA, Piggott MJ, Duggan PJ (July 2023). "Introduction to the chemistry and pharmacology of psychedelic drugs". Australian Journal of Chemistry. 76 (5): 236–257. doi:10.1071/CH23050.
- ^ Mallaroni P, Mason NL, Vinckenbosch FRJ, Ramaekers JG (April 2022). "The use patterns of novel psychedelics: experiential fingerprints of substituted phenethylamines, tryptamines and lysergamides". Psychopharmacology. 239 (6): 1783–1796. doi:10.1007/s00213-022-06142-4. PMC 9166850. PMID 35487983.
- ^ Nichols DE (February 2004). "Hallucinogens". Pharmacology & Therapeutics. 101 (2): 131–181. doi:10.1016/j.pharmthera.2003.11.002. ISSN 1879-016X. PMID 14761703.
- ^ 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.
- ^ Carhart-Harris RL, Muthukumaraswamy S, Roseman L, Kaelen M, Droog W, Murphy K, et al. (April 11, 2016). "Neural correlates of the LSD experience revealed by multimodal neuroimaging". Proceedings of the National Academy of Sciences of the United States of America. 113 (17): 4853–4858. Bibcode:2016PNAS..113.4853C. doi:10.1073/pnas.1518377113. PMC 4855588. PMID 27071089.
- ^ Cite error: The named reference
pmid24309097was invoked but never defined (see the help page). - ^ Cite error: The named reference
nichols_closes_shopwas invoked but never defined (see the help page). - ^ Hofmann A (2009). LSD, my problem child: reflections on sacred drugs, mysticism, and science (4th ed.). Santa Cruz, CA: Multidisciplinary Association for Psychedelic Studies. ISBN 978-0-9798622-2-9. OCLC 610059315.
- ^ a b c d e f Lee MA, Shlain B (1992). Acid dreams: the complete social history of LSD: the CIA, the Sixties, and beyond. New York: Grove Weidenfeld. ISBN 0-8021-3062-3. OCLC 25281992.
- ^ Ettinger RH (2017). Psychopharmacology. Psychology Press. p. 226. ISBN 978-1-351-97870-5. Archived from the original on September 27, 2021. Retrieved September 27, 2021.
- ^ "Psychiatric Research with Hallucinogens". www.druglibrary.org. Archived from the original on July 26, 2021. Retrieved July 26, 2021.
- ^ 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.
- ^ Krebs TS, Johansen PØ (July 2012). "Lysergic acid diethylamide (LSD) for alcoholism: meta-analysis of randomized controlled trials". Journal of Psychopharmacology. 26 (7): 994–1002. doi:10.1177/0269881112439253. PMID 22406913. S2CID 10677273.
- ^ 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.
- ^ National Institute on Drug Abuse. "Hallucinogens". Archived from the original on June 3, 2020. Retrieved July 14, 2018.
- ^ 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.