Editing LSD (section)

{{Short description|Hallucinogenic drug}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Redirect-distinguish|Lsd|£sd}}
{{Other uses}}
{{Use mdy dates|date=May 2016}}
{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 629704081
| drug_name = Lysergic acid diethylamide
| INN = Lysergide
| type = 
| IUPAC_name = (6a''R'',9''R'')-''N'',''N''-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-''fg'']quinoline-9-carboxamide
| image = LSD skeletal formula.svg
| image_class = skin-invert-image
| width = 150px
| caption = [[Skeletal formula]]  of LSD
| image2 = LSD-from-xtal-and-Spartan-PM3-3D-balls-web.png
| width2 = 175px
| caption2 = [[Ball-and-stick model|3D stick model]] of LSD

<!-- Clinical data -->
| pronounce = {{IPA|/daɪ eθəl ˈæmaɪd/}}, {{IPA|/æmɪd/}}, or {{IPA|/eɪmaɪd/}}<ref>{{cite encyclopedia |url=http://www.collinsdictionary.com/dictionary/english/amide |title=Definition of "amide" |dictionary=Collins English Dictionary |access-date=January 31, 2015 |url-status=live |archive-url=https://web.archive.org/web/20150402115318/http://www.collinsdictionary.com/dictionary/english/amide |archive-date=April 2, 2015}}</ref><ref>{{cite web |url=https://www.ahdictionary.com/word/search.html?q=amide |title=American Heritage Dictionary Entry: amide |publisher=Ahdictionary.com |access-date=January 31, 2015 |archive-url=https://web.archive.org/web/20150402134025/https://www.ahdictionary.com/word/search.html?q=amide |archive-date=April 2, 2015}}</ref><ref>{{cite web |url=http://www.oxforddictionaries.com/us/definition/english/amide |title=amide – definition of amide in English from the ''Oxford Dictionary''|publisher=Oxforddictionaries.com |access-date=January 31, 2015 |archive-url=https://web.archive.org/web/20150402184403/http://www.oxforddictionaries.com/us/definition/english/amide |archive-date=April 2, 2015}}</ref>
| Drugs.com = [https://www.drugs.com/illicit/lsd.html Reference]
| pregnancy_US = C
| MedlinePlus = 
| licence_EU = 
| licence_US = 
| pregnancy_AU = 
| pregnancy_category = C
| tradename = Delysid
| addiction_liability = None<ref name="NHM-MDMA"/>
| dependency_liability = Low<ref>{{cite book| vauthors = Halpern JH, Suzuki J, Huertas PE, Passie T | veditors = Price LH, Stolerman IP |title=Encyclopedia of Psychopharmacology A Springer Live Reference|date=June 7, 2014|publisher=Springer-Verlag Berlin Heidelberg|location=Heidelberg, Germany|isbn=978-3-642-27772-6|pages=1–5|quote=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 |doi=10.1007/978-3-642-27772-6_43-2|chapter=Hallucinogen Abuse and Dependence}}</ref>
| routes_of_administration = [[By mouth]], [[Sublingual administration|sublingual]]
| class = [[Serotonin receptor agonist]]; [[Serotonin]] [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] [[agonist]]; [[Serotonergic psychedelic]]; [[Hallucinogen]]

<!-- Legal status -->
| legal_AU = Schedule 9
| legal_BR = F2
| legal_CA = Schedule III
| legal_NZ = Class A
| legal_UK = Class A
| legal_UN = P I
| legal_US = Schedule I
| legal_DE = Anlage I
| legal_status = [[Illicit drug]]

<!-- Pharmacokinetic data -->
| bioavailability = 81%<ref name="Holze_2024">{{cite journal | vauthors = Holze F, Mueller L, Vizeli P, Luethi D, Rudin D, Hysek C, Liechti M, Arikci D | title = Oral LSD base and tartrate bioequivalence and absolute bioavailability in healthy participants | journal = Neuroscience Applied | volume = 3 | pages = 105132 | date = 2024 | doi = 10.1016/j.nsa.2024.105132 | doi-access = free }}</ref>
| protein_bound = Unknown<ref name="PassieHalpernStrichtenoth2008" />
| metabolism = [[Liver]] ([[CYP450]])<ref name=Dol2015 />
| metabolites = 2-Oxo-3-hydroxy-LSD<ref name=Dol2015 />
| onset = [[Oral administration|Oral]]: 0.4–1.0 (range 0.1–1.8) hours<ref name="HolzeSinghLiechti2024" /><ref name="PassieHalpernStrichtenoth2008" /><br />{{Abbrlink|IM|Intramuscular injection}}: 15–20 min<ref name="PassieHalpernStrichtenoth2008" /><br />{{Abbrlink|IV|Intravenous injection}}: 3–40 min<ref name="PassieHalpernStrichtenoth2008" /><ref name="GumpperNichols2024" /><ref name="Shulgin1980b">{{cite journal | vauthors = Shulgin AT | title = Profiles of Psychedelic Drugs: LSD | journal = J Psychedelic Drugs | volume = 12 | issue = 2 | pages = 173–174 | date = 1980 | pmid = 7420434 | doi = 10.1080/02791072.1980.10471571 | url = }}</ref><br />{{Abbrlink|IT|Intrathecal injection}}: <1 min<ref name="PassieHalpernStrichtenoth2008" /><ref name="Shulgin1980b" />
| duration_of_action = [[Oral administration|Oral]]: 7–12 (range 4–22) hours<ref name="HolzeSinghLiechti2024" /><ref name="PassieHalpernStrichtenoth2008" /><br />{{Abbrlink|IM|Intramuscular injection}}, {{Abbrlink|IV|Intravenous injection}}, {{Abbrlink|IT|Intrathecal injection}}: 9–10 hours<ref name="PassieHalpernStrichtenoth2008" />
| elimination_half-life = 3.6{{nbsp}}hours<ref name=Dol2015/><ref name=Muc2016/>
| excretion = [[Kidneys]]<ref name=Dol2015 /><ref name=Muc2016 />

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 50-37-3
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 6605
| PubChem = 5761
| IUPHAR_ligand = 17
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB04829
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5558
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8NA5SWF92O
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C07542
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 263881
| ATC_prefix = None
| PDB_ligand = 7LD
| synonyms = LSD; LSD-25; LAD; Acid; Lucy; Lysergide; 9,10-Didehydro-''N'',''N''-diethyl-6-methylergoline-8β-carboxamide; ''N'',''N''-Diethyl-''d''-lysergamide; ''d''-Lysergic acid diethylamide; METH-LAD; EA-1729

<!-- Chemical data -->
| C=20 | H=25 | N=3 | O=1
| SMILES = CCN(CC)C(=O)[C@H]1CN([C@@H]2Cc3c[nH]c4c3c(ccc4)C2=C1)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VAYOSLLFUXYJDT-RDTXWAMCSA-N

<!-- Physical data -->
| melting_point = 80
| melting_high = 85
| solubility = 67.02<ref>{{cite web|title=Lysergide|url=https://pubchem.ncbi.nlm.nih.gov/compound/5761#section=Solubility|website=pubchem.ncbi.nlm.nih.gov|language=en|access-date=April 12, 2023|archive-date=April 12, 2023|archive-url=https://web.archive.org/web/20230412075752/https://pubchem.ncbi.nlm.nih.gov/compound/5761#section=Solubility|url-status=live}}</ref>
}}

'''Lysergic acid diethylamide''', commonly known as '''LSD''' (from German {{lang|de|Lysergsäure-diethylamid}}; often referred to as '''acid''' or '''lucy'''), is a [[Semisynthesis|semisynthetic]], non-addictive [[Hallucinogen|hallucinogenic]] compound derived from [[ergot]], known for its powerful psychological effects and [[Serotonin|serotonergic]] activity.<ref>{{Cite web |last=PubChem |title=Lysergide |url=https://pubchem.ncbi.nlm.nih.gov/compound/Lysergide |access-date=2025-05-22 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> 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).<ref name="HolzeSinghLiechti2024" /><ref name="PassieHalpernStrichtenoth2008" /> It is commonly administered via tabs of [[Blotting paper|blotter paper]].<ref name="NIH2016">{{cite web |title=What are hallucinogens? |date=January 2016 |url=https://www.drugabuse.gov/publications/drugfacts/hallucinogens |website=National Institute of Drug Abuse |access-date=April 24, 2016 |url-status=live |archive-url=https://web.archive.org/web/20160417180046/https://www.drugabuse.gov/publications/drugfacts/hallucinogens |archive-date=April 17, 2016}}</ref>  LSD is extremely potent, with noticeable effects at doses as low as 20 [[Microgram|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.<ref name="EU2018">{{cite web |title=LSD profile (chemistry, effects, other names, synthesis, mode of use, pharmacology, medical use, control status) |url=http://www.emcdda.europa.eu/publications/drug-profiles/lsd |url-status=live |archive-url=https://web.archive.org/web/20210428113546/https://www.emcdda.europa.eu/publications/drug-profiles/lsd |archive-date=April 28, 2021 |access-date=14 July 2018 |website=EMCDDA |language=en}}</ref><ref>{{cite news |vauthors=Gershon L |date=19 July 2016 |title=How LSD Went From Research to Religion |url=https://daily.jstor.org/how-lsd-went-from-research-to-religion/ |access-date=14 July 2018 |work=JSTOR Daily |archive-date=January 28, 2021 |archive-url=https://web.archive.org/web/20210128015545/https://daily.jstor.org/how-lsd-went-from-research-to-religion/ |url-status=live }}</ref> LSD can cause mystical experiences.<ref>{{cite journal |vauthors=Liechti ME, Dolder PC, Schmid Y |date=May 2017 |title=Alterations of consciousness and mystical-type experiences after acute LSD in humans |journal=Psychopharmacology |volume=234 |issue=9–10 |pages=1499–1510 |doi=10.1007/s00213-016-4453-0 |pmc=5420386 |pmid=27714429}}</ref><ref>{{cite journal |vauthors=Griffiths RR, Hurwitz ES, Davis AK, Johnson MW, Jesse R |date=2019-04-23 |title=Survey of subjective "God encounter experiences": Comparisons among naturally occurring experiences and those occasioned by the classic psychedelics psilocybin, LSD, ayahuasca, or DMT |journal=PLOS ONE |volume=14 |issue=4 |pages=e0214377 |bibcode=2019PLoSO..1414377G |doi=10.1371/journal.pone.0214377 |pmc=6478303 |pmid=31013281 |doi-access=free}}</ref> LSD exerts its effects primarily through high-affinity binding to several [[5-HT receptor|serotonin receptors]], especially [[5-HT2A receptor|5-HT<sub>2A</sub>]], and to a lesser extent [[dopaminergic]] and [[adrenergic]] receptors. LSD reduces oscillatory power in the brain’s [[default mode network]] and flattens brain hierarchy.<ref name="Nichols2016">{{cite journal |vauthors=Nichols DE |date=April 2016 |title=Psychedelics |journal=Pharmacological Reviews |volume=68 |issue=2 |pages=264–355 |doi=10.1124/pr.115.011478 |issn=0031-6997 |pmc=4813425 |pmid=26841800 |veditors=Barker EL}}</ref><ref>{{Cite journal |vauthors=Girn M, Roseman L, Bernhardt B, Smallwood J, Carhart-Harris R, Spreng RN |date=2020-05-03|title=Serotonergic psychedelic drugs LSD and psilocybin reduce the hierarchical differentiation of unimodal and transmodal cortex |journal=bioRxiv |s2cid=233346402 |doi=10.1101/2020.05.01.072314 |doi-access=free}}</ref> At higher doses, it can induce visual and auditory hallucinations, [[Ego death|ego dissolution]], and [[anxiety]].<ref name="LeptourgosFortier-Davy2020">{{cite journal |vauthors=Leptourgos P, Fortier-Davy M, Carhart-Harris R, Corlett PR, Dupuis D, Halberstadt AL, Kometer M, Kozakova E, LarØi F, Noorani TN, Preller KH, Waters F, Zaytseva Y, Jardri R |date=December 2020 |title=Hallucinations Under Psychedelics and in the Schizophrenia Spectrum: An Interdisciplinary and Multiscale Comparison |journal=Schizophrenia Bulletin |volume=46 |issue=6 |pages=1396–1408 |doi=10.1093/schbul/sbaa117 |pmc=7707069 |pmid=32944778}}</ref><ref name=":3">{{cite journal |vauthors=Holze F, Vizeli P, Ley L, Müller F, Dolder P, Stocker M, Duthaler U, Varghese N, Eckert A, Borgwardt S, Liechti ME |date=February 2021 |title=Acute dose-dependent effects of lysergic acid diethylamide in a double-blind placebo-controlled study in healthy subjects |journal=Neuropsychopharmacology |volume=46 |issue=3 |pages=537–544 |doi=10.1038/s41386-020-00883-6 |pmc=8027607 |pmid=33059356}}</ref> LSD use can cause adverse psychological effects such as [[paranoia]] and [[Delusion|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.<ref name="EU2018" /><ref name="NIH2018C">{{cite web |title=Commonly Abused Drugs Charts |url=https://www.drugabuse.gov/drugs-abuse/commonly-abused-drugs-charts#lsd |website=National Institute on Drug Abuse |access-date=14 July 2018 |date=2 July 2018 |url-status=live |archive-url=https://web.archive.org/web/20200301183029/https://www.drugabuse.gov/drugs-abuse/commonly-abused-drugs-charts#lsd |archive-date=March 1, 2020}}</ref> It was initially explored for psychiatric use due to its structural similarity to serotonin and safety profile.<ref name="Nichols2018a">{{cite journal |vauthors=Nichols DE |date=October 2018 |title=Dark Classics in Chemical Neuroscience: Lysergic Acid Diethylamide (LSD) |url=https://shaunlacob.com/wp-content/uploads/2020/12/DC-LSD.pdf |journal=ACS Chemical Neuroscience |volume=9 |issue=10 |pages=2331–2343 |doi=10.1021/acschemneuro.8b00043 |pmid=29461039}}</ref> It was used experimentally in [[psychiatry]] for treating [[alcoholism]] and [[schizophrenia]].<ref name="Use of d-lysergic acid diethylamide">{{cite journal |vauthors=Chwelos N, Blewett DB, Smith CM, Hoffer A |title=Use of d-lysergic acid diethylamide in the treatment of alcoholism |journal=Quarterly Journal of Studies on Alcohol |volume=20 |issue=3 |pages=577–590 |date=September 1959 |pmid=13810249 |doi=10.15288/qjsa.1959.20.577}}</ref>  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 [[Controlled Substances Act#Schedule I controlled substances|Schedule I]] drug in the U.S. in 1968.<ref>{{Cite book |author=United States Congress House Committee on Interstate and Foreign Commerce Subcommittee on Public Health and Welfare |url=https://books.google.com/books?id=qbY6xQEACAAJ |title=Increased Controls Over Hallucinogens and Other Dangerous Drugs |date=1968 |publisher=U.S. Government Printing Office |access-date=August 3, 2021|archive-date=July 13, 2020 |archive-url=https://web.archive.org/web/20200713014802/https://books.google.com/books?id=qbY6xQEACAAJ|url-status=live}}</ref> It was also listed as a [[Schedule 1 controlled substance|Schedule I controlled substance]] by the [[United Nations]] in 1971 and remains without approved medical uses.<ref name="EU2018" />

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 [[United States]] [[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.<ref name="NIH2018B">{{cite web|author=National Institute on Drug Abuse|title=Hallucinogens |url=https://www.drugabuse.gov/drugs-abuse/hallucinogens |access-date=14 July 2018|archive-date=June 3, 2020|archive-url=https://web.archive.org/web/20200603125635/https://www.drugabuse.gov/drugs-abuse/hallucinogens|url-status=live}}</ref> Usage rates have risen, with a 56.4% increase in adult use in the U.S. from 2015 to 2018.<ref>{{cite journal |vauthors=Yockey RA, Vidourek RA, King KA |title=Trends in LSD use among US adults: 2015–2018 |journal=Drug and Alcohol Dependence |volume=212 |pages=108071 |date=July 2020 |pmid=32450479 |doi=10.1016/j.drugalcdep.2020.108071 |s2cid=218893155}}</ref>

{{TOC limit}}