Editing LSD (section)

==Chemistry==
[[File:Lysergide stereoisomers structural formulae v.2.png|class=skin-invert-image|thumb|upright=1.35|The four possible stereoisomers of LSD. Only (+)-LSD is psychoactive.]]

LSD is a [[chirality (chemistry)|chiral]] compound with two [[stereocenter]]s at the [[carbon]] atoms C-5 and C-8, so that theoretically four different [[optical isomerism|optical isomers]] of LSD could exist. LSD, also called (+)-''d''-LSD,<ref>{{Cite book |title=Handbook of Medical Hallucinogens |date=2021 |publisher=Guilford Publications |isbn=9781462545452 |pages=160 |language=en |chapter=LSD |chapter-url=https://mcb.berkeley.edu/labs2/presti/sites/mcb.berkeley.edu.labs2.presti/files/u3/2021%20LSD%20Chapter%20Panik%20Presti.pdf |access-date=March 14, 2024 |archive-date=March 14, 2024 |archive-url=https://web.archive.org/web/20240314163910/https://mcb.berkeley.edu/labs2/presti/sites/mcb.berkeley.edu.labs2.presti/files/u3/2021%20LSD%20Chapter%20Panik%20Presti.pdf |url-status=live }}</ref> has the [[absolute configuration]] (5''R'',8''R''). 5''S'' stereoisomers of lysergamides do not exist in nature and are not formed during the synthesis from [[Descriptor (chemistry)#dl|''d'']]-lysergic acid. [[Retrosynthesis|Retrosynthetically]], the C-5 stereocenter could be analysed as having the same configuration of the alpha carbon of the naturally occurring amino acid L-[[tryptophan]], the precursor to all biosynthetic ergoline compounds.

However, LSD and iso-LSD, the two C-8 isomers, rapidly interconvert in the presence of [[base (chemistry)|bases]], as the alpha proton is acidic and can be [[deprotonated]] and reprotonated. Non-psychoactive iso-LSD which has formed during the synthesis can be separated by [[chromatography]] and can be isomerized to LSD.

Pure salts of LSD are [[triboluminescent]], emitting small flashes of white light when shaken in the dark.<ref name="tihkal" /> LSD is strongly [[fluorescent]] and will glow bluish-white under [[UV light]].

===Synthesis===
LSD is an [[ergoline]] derivative. It is commonly synthesized by reacting [[diethylamine]] with an activated form of [[lysergic acid]]. Activating reagents include [[phosphoryl chloride]]<ref name="synth1">{{cite journal |vauthors=Monte AP, Marona-Lewicka D, Kanthasamy A, Sanders-Bush E, Nichols DE |date=March 1995 |title=Stereoselective LSD-like activity in a series of d-lysergic acid amides of (R)- and (S)-2-aminoalkanes |journal=Journal of Medicinal Chemistry |volume=38 |issue=6 |pages=958–66 |pmid=7699712 |doi=10.1021/jm00006a015}}</ref> and [[peptide coupling reagent]]s.<ref name="synth2">{{cite journal |vauthors=Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM |date=September 2002 |title=Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD) |journal=Journal of Medicinal Chemistry |volume=45 |issue=19 |pages=4344–9 |pmid=12213075 |doi=10.1021/jm020153s}}</ref> Lysergic acid is made by alkaline [[hydrolysis]] of lysergamides like [[ergotamine]], a substance usually derived from the [[ergot]] [[fungus]] on [[agar plate]]. Lysergic acid can also be produced synthetically, although these processes are not used in clandestine manufacture due to their low yields and high complexity.<ref>{{cite journal |vauthors=Kornfeld EC, Fornefeld EJ, Kline GB, Mann MJ, Morrison DE, Jones RG, Woodward RB |title=The Total Synthesis of Lysergic Acid |journal=Journal of the American Chemical Society |volume=78 |issue=13 |pages=3087–3114 |year=1956 |doi=10.1021/ja01594a039|bibcode=1956JAChS..78.3087K }}</ref><ref>{{cite journal |vauthors=Inuki S, Oishi S, Fujii N, Ohno H |title=Total synthesis of (+/-)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group |journal=Organic Letters |volume=10 |issue=22 |pages=5239–42 |date=November 2008 |pmid=18956869 |doi=10.1021/ol8022648 |url=https://figshare.com/articles/journal_contribution/2663242}}</ref>

Albert Hofmann synthesized LSD in the following manner: (1) hydrazinolysis of ergotamine into D- and L-isolysergic acid hydrazide, (2) separation of the enantiomers with di-(''p''-toluyl)-D-tartaric acid to get D-isolysergic acid hydrazide, (3) enantiomerization into D-lysergic acid hydrazide, (4) substitution with [[Nitrous acid|HNO<sub>2</sub>]] to D-lysergic acid azide and (5) finally substitution with [[diethylamine]] to form D-lysergic acid diethylamide.<ref name="Nichols2018a" />

====Research====
The precursor for LSD, [[lysergic acid]], has been produced by [[GMO]] [[baker's yeast]].<ref>{{cite web |author=((National University of Singapore, Yong Loo Lin School of Medicine)) |date=10 February 2022 |title=Harvesting baker's yeast for aging-related therapeutics |website=ScienceDaily |url=https://www.sciencedaily.com/releases/2022/02/220210154135.htm |access-date=2023-05-04 |archive-date=November 27, 2022 |archive-url=https://web.archive.org/web/20221127230250/https://www.sciencedaily.com/releases/2022/02/220210154135.htm |url-status=live }} '''Journal Reference:''' {{cite journal |vauthors=Wong G, Lim LR, Tan YQ, Go MK, Bell DJ, Freemont PS, Yew WS |title=Reconstituting the complete biosynthesis of D-lysergic acid in yeast |journal=Nature Communications |volume=13 |issue=1 |pages=712 |date=February 2022 |doi=10.1038/s41467-022-28386-6 |pmid=35132076 |pmc=8821704 |bibcode=2022NatCo..13..712W}}</ref>

===Stability===
"LSD," writes the chemist [[Alexander Shulgin]], "is an unusually fragile molecule ... As a salt, in water, cold, and free from air and light exposure, it is stable indefinitely."<ref name="tihkal" />

LSD has two [[labile]] protons at the tertiary stereogenic C5 and C8 positions, rendering these centers prone to [[epimerisation]]. The C8 proton is more labile due to the electron-withdrawing [[carboxamide]] attachment, but the removal of the [[chiral]] proton at the C5 position (which was once also an alpha proton of the parent molecule [[tryptophan]]) is assisted by the inductively withdrawing nitrogen and pi electron delocalisation with the [[indole]] ring.{{Citation needed|date=May 2011}}

LSD also has [[enamine]]-type reactivity because of the electron-donating effects of the indole ring. Because of this, [[chlorine]] destroys LSD molecules on contact; even though chlorinated tap water contains only a slight amount of chlorine, the small quantity of compound typical to an LSD solution will likely be eliminated when dissolved in tap water.<ref name="tihkal" /> The [[covalent bond|double bond]] between the 8-position and the [[aromatic hydrocarbon|aromatic ring]], being conjugated with the indole ring, is susceptible to [[nucleophilic]] attacks by water or [[alcohol (chemistry)|alcohol]], especially in the presence of UV or other kinds of light. LSD often converts to "lumi-LSD," which is inactive in human beings.<ref name="tihkal" />

A controlled study was undertaken to determine the stability of LSD in pooled urine samples.<ref>{{cite journal | vauthors = Li Z, McNally AJ, Wang H, Salamone SJ | title = Stability study of LSD under various storage conditions | journal = Journal of Analytical Toxicology | volume = 22 | issue = 6 | pages = 520–5 | date = October 1998 | pmid = 9788528 | doi = 10.1093/jat/22.6.520 | doi-access = free }}</ref>

The concentrations of LSD in urine samples were followed over time at various temperatures, in different types of storage containers, at various exposures to different wavelengths of light, and at varying pH values. These studies demonstrated no significant loss in LSD concentration at 25&nbsp;°C for up to four weeks. After four weeks of incubation, a 30% loss in LSD concentration at 37&nbsp;°C and up to a 40% at 45&nbsp;°C were observed. Urine fortified with LSD and stored in amber glass or nontransparent polyethylene containers showed no change in concentration under any light conditions. The stability of LSD in transparent containers under light was dependent on the distance between the light source and the samples, the wavelength of light, exposure time, and the intensity of light. After prolonged exposure to heat in alkaline pH conditions, 10 to 15% of the parent LSD epimerized to iso-LSD. Under acidic conditions, less than 5% of the LSD was converted to iso-LSD. It was also demonstrated that trace amounts of metal ions in the buffer or urine could catalyze the decomposition of LSD and that this process can be avoided by the addition of [[EDTA]].

===Detection===
[[File:LSD Ehrlich reagent test.jpg|thumb|[[Ehrlich's reagent]] can be used to test for the presence of LSD in a sample, turning purple upon reaction.<ref name="LSDEMCDDA">{{cite web |url=https://www.emcdda.europa.eu/publications/drug-profiles/lsd_en |title=Lysergide (LSD) drug profile |website=[[European Monitoring Centre for Drugs and Drug Addiction]] (EMCDDA) |access-date=15 May 2023 |url-status=live |archive-url=https://web.archive.org/web/20230202152854/https://www.emcdda.europa.eu/publications/drug-profiles/lsd_en |archive-date=2 February 2023}}</ref>]]

LSD can be detected in concentrations larger than approximately 10% in a sample using [[Ehrlich's reagent]] and [[Hofmann's reagent]]. However, detecting LSD in human tissues is more challenging due to its active dosage being significantly lower (in [[micrograms]]) compared to most other drugs (in [[milligrams]]).<ref name="ReferenceA">{{Cite journal | vauthors = Appel JB, Whitehead WE, Freedman DX |date= July 1968 |title=Motivation and the behavioral effects of LSD |journal=Psychonomic Science |language=en |volume=12 |issue=7 |pages=305–306 |doi=10.3758/BF03331322 |s2cid=144527673 |issn=0033-3131|doi-access=free }}</ref>

LSD may be quantified in urine for drug testing programs, in plasma or serum to confirm poisoning in hospitalized victims, or in whole blood for forensic investigations. The parent drug and its major metabolite are unstable in biofluids when exposed to light, heat, or alkaline conditions, necessitating protection from light, low-temperature storage, and quick analysis to minimize losses.<ref>R. Baselt, ''Disposition of Toxic Drugs and Chemicals in Man'', 12th edition, Biomedical Publications, Foster City, CA, 2020, pp. 1197–1199.</ref> Maximum plasma concentrations are typically observed 1.4 to 1.5 hours after oral administration of 100&nbsp;μg and 200&nbsp;μg, respectively, with a plasma half-life of approximately 2.6 hours (ranging from 2.2 to 3.4 hours among test subjects).<ref>{{cite journal | vauthors = Dolder PC, Schmid Y, Steuer AE, Kraemer T, Rentsch KM, Hammann F, Liechti ME | title = Pharmacokinetics and Pharmacodynamics of Lysergic Acid Diethylamide in Healthy Subjects | journal = Clinical Pharmacokinetics | volume = 56 | issue = 10 | pages = 1219–1230 | date = October 2017 | pmid = 28197931 | doi = 10.1007/s40262-017-0513-9 | pmc = 5591798 }}</ref>

Due to its potency in microgram quantities, LSD is often not included in standard pre-employment urine or hair analyses.<ref name="ReferenceA"/><ref name="pmid36753839">{{cite journal |vauthors=Jiaming Z, Xin W, Jiali Z, Hang R, Yunli Z, Ping X |title=Concentrations of LSD, 2-oxo-3-hydroxy-LSD, and iso-LSD in hair segments of 18 drug abusers |journal=Forensic Science International |volume=344 |date=March 2023 |pmid=36753839 |doi=10.1016/j.forsciint.2023.111578| s2cid=256574276}}</ref> However, advanced [[liquid chromatography–mass spectrometry]] methods can detect LSD in biological samples even after a single use.<ref name="pmid36753839"/>

===Analogues===
{{Main|Lysergamides|Lysergamides#Simplified or partial lysergamides}}

A variety of LSD [[structural analogue|analogue]]s are known.<ref name="Shulgin2003">{{cite book | vauthors = Shulgin AT | chapter=Basic Pharmacology and Effects | pages=67–137 | veditors = Laing RR | title=Hallucinogens: A Forensic Drug Handbook | publisher=Elsevier Science | series=Forensic Drug Handbook Series | year=2003 | isbn=978-0-12-433951-4 | url=https://books.google.com/books?id=l1DrqgobbcwC | chapter-url=https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6 | access-date=1 February 2025}}</ref><ref name="JacobShulgin1994">{{cite journal | vauthors = Jacob P, Shulgin AT | title = Structure-activity relationships of the classic hallucinogens and their analogs | journal = NIDA Res Monogr | volume = 146 | issue = | pages = 74–91 | date = 1994 | pmid = 8742795 | doi = | url = https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79 }}</ref><ref name="Shulgin1982">{{cite book |vauthors=Shulgin AT | chapter=Chemistry of Psychotomimetics | pages = 3–29 | veditors = Hoffmeister F, Stille G | title=Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs | series=Handbook of Experimental Pharmacology | publisher=Springer Berlin Heidelberg |location=Berlin |date=1982 | volume=55 / 3 |isbn=978-3-642-67772-4 | oclc = 8130916 | doi=10.1007/978-3-642-67770-0_1 | url = https://books.google.com/books?id=mrT8CAAAQBAJ | chapter-url = https://bitnest.netfirms.com/external/10.1007/978-3-642-67770-0_1}}</ref><ref name="Shulgin1980">{{cite book | author = Alexander T. Shulgin | chapter = Hallucinogens | pages = 1109–1137 | chapter-url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6ac0c892ee380436f614d3aae0686ef617b2e0c5 | veditors = Burger A, Wolf ME | title = Burger's Medicinal Chemistry | edition = 4 | volume = 3 | date = 1980 | publisher = Wiley | location = New York | isbn = 978-0-471-01572-7 | oclc = 219960627 | url = https://books.google.com/books?id=2b3wAAAAMAAJ}}</ref><ref name="TiHKAL">{{CiteTiHKAL}}</ref> Many of them retain psychedelic effects similarly to LSD, although most have reduced [[potency (pharmacology)|potency]] and none are notably more potent than LSD.<ref name="Shulgin2003" /><ref name="JacobShulgin1994" /><ref name="Shulgin1982" /><ref name="Shulgin1980" /><ref name="Mangner1978">{{cite thesis | vauthors = Mangner TJ | degree = Ph.D. | publisher = University of Michigan | title=Potential Psychotomimetic Antagonists. N,n -diethyl-1-methyl-3-aryl-1, 2, 5, 6-tetrahydropyridine-5-carboxamides. | date=1978 | doi=10.7302/11268 | url=https://www.proquest.com/openview/f845a6810749d00f70305960adfde737/ | archive-url=https://web.archive.org/web/20250330031605/https://media.proquest.com/media/hms/ORIG/2/9yQxJ?cit%3Aauth=MANGNER%2C+THOMAS+JOSEPH&cit%3Atitle=POTENTIAL+PSYCHOTOMIMETIC+ANTAGONISTS.+N%2CN+...&cit%3Apub=ProQuest+Dissertations+and+Theses&cit%3Avol=&cit%3Aiss=&cit%3Apg=&cit%3Adate=1978&ic=true&cit%3Aprod=ProQuest+Dissertations+%26+Theses+Global&_a=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&_s=QP3F3liRMGFAbHtX3wDWE8eO1gs%3D#page=22 | archive-date=30 March 2025}}</ref> Examples include [[ergine]] (lysergic acid amide; LSA), [[ergonovine]] (ergometrine), [[methylergonovine]] (methylergometrine), [[methysergide]], [[ETH-LAD]], [[AL-LAD]], [[1-methyl-LSD]] (MLD-41), and [[LA-SS-Az]] (LSZ), among many others.<ref name="Shulgin2003" /><ref name="RutschmannStadler1978">{{cite book | vauthors = Rutschmann J, Stadler PA | chapter=Chemical Background | veditors=Berde B, Schild HO | title=Ergot Alkaloids and Related Compounds | publisher=Springer Berlin Heidelberg | publication-place=Berlin, Heidelberg | date=1978 | isbn=978-3-642-66777-0 | doi=10.1007/978-3-642-66775-6_2 | pages=29–85 | series=Handbook of Experimental Pharmacology (HEP) | volume=49}}</ref><ref name="Fanchamps1978">{{cite book | vauthors = Fanchamps A | chapter=Some Compounds With Hallucinogenic Activity | veditors=Berde B, Schild HO | title=Ergot Alkaloids and Related Compounds | publisher=Springer Berlin Heidelberg | publication-place=Berlin, Heidelberg | date=1978 | isbn=978-3-642-66777-0 | doi=10.1007/978-3-642-66775-6_8 | pages=567–614 | series=Handbook of Experimental Pharmacology (HEP) | volume=49 | chapter-url=https://bibliography.maps.org/resources/download/8769| archive-url=https://web.archive.org/web/20250330033128/https://bibliography.maps.org/resources/download/8769 | archive-date=March 30, 2025 }}</ref> Presumed or known [[prodrug]]s of LSD, including [[1A-LSD]] (ALD-52), [[1P-LSD]], and [[1V-LSD]], have been developed or encountered.<ref name="SchifanoVentoScherbaum2023">{{cite journal | vauthors = Schifano F, Vento A, Scherbaum N, Guirguis A | title = Stimulant and hallucinogenic novel psychoactive substances; an update | journal = Expert Rev Clin Pharmacol | volume = 16 | issue = 11 | pages = 1109–1123 | date = 2023 | pmid = 37968919 | doi = 10.1080/17512433.2023.2279192 | url = | hdl = 2299/27223 | hdl-access = free }}</ref><ref name="Ponce2024">{{cite journal | vauthors = Ponce JC | title=The use of prodrugs as drugs of abuse | journal=WIREs Forensic Science | volume=6 | issue=3 | date=2024 | issn=2573-9468 | doi=10.1002/wfs2.1514 | doi-access=free | page=}}</ref> Some non-[[hallucinogen]]ic LSD analogues, such as [[lisuride]] and [[2-bromo-LSD]] (BOL-148), are known as well.<ref name="GumpperNichols2024">{{cite journal | vauthors = Gumpper RH, Nichols DE | title = Chemistry/structural biology of psychedelic drugs and their receptor(s) | journal = Br J Pharmacol | volume = | issue = | pages = | date = October 2024 | pmid = 39354889 | doi = 10.1111/bph.17361 | url = }}</ref><ref name="PfaffHuangMarona-Lewicka1994" /><ref name="Nichols2012">{{cite journal | vauthors = Nichols DE | title=Structure–activity relationships of serotonin 5-HT 2A agonists | journal=Wiley Interdisciplinary Reviews: Membrane Transport and Signaling | volume=1 | issue=5 | date=2012 | issn=2190-460X | doi=10.1002/wmts.42 | doi-access=free | pages=559–579 | access-date=22 March 2025 | url=https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=e28e0e22c3145af5a787c34fbedbaa8f81e1ed6b}}</ref> They are lower-[[intrinsic activity|efficacy]] [[serotonin]] [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] [[partial agonist]]s and can notably act as [[hallucinogen antagonist]]s against LSD.<ref name="PfaffHuangMarona-Lewicka1994">{{cite journal | vauthors = Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE | title = Lysergamides revisited | journal = NIDA Res Monogr | volume = 146 | issue = | pages = 52–73 | date = 1994 | pmid = 8742794 | doi = | url = https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=57}}</ref><ref name="Nichols2012" /> In addition to [[lysergamide]] [[chemical derivative|derivative]]s, [[simplified LSD analogue|simplified or "partial" LSD analogues]], such as [[NDTDI]], [[N-DEAOP-NMT|''N''-DEAOP-NMT]], and [[DEIMDHPCA]], are known.<ref name="Shulgin1976">{{cite book | veditors=Gordon M | title=Psychopharmacological Agents: Use, Misuse and Abuse | series=Medicinal Chemistry: A Series of Monographs | volume=4 | vauthors = Shulgin AT | chapter=Psychotomimetic Agents | date=1976 | isbn=978-0-12-290559-9 | doi=10.1016/b978-0-12-290559-9.50011-9 | pages=59–146 | publisher=Academic Press | url=https://bitnest.netfirms.com/external/10.1016/B978-0-12-290559-9.50011-9 | quote = The largest number of structural analogs of LSD that have been prepared involve the opening of one or more of the rings of the parent lysergic acid system. [...] A recent review covers this chemistry (Campaigne and Knapp, 1971), but there is apparently no human psychopharmacology as yet known.}}</ref><ref name="Nichols1973">{{cite thesis | vauthors = [[David E. Nichols|Nichols DE]] | title = Potential Psychotomimetics: Bromomethoxyamphetamines and Structural Congeners of Lysergic Acid | date = May 1973 | publisher = [[University of Iowa]] | pages = 23 | oclc = 1194694085 | url = https://bitnest.netfirms.com/external/Theses/Nichols1973#page=32}}</ref><ref name="CampaigneKnapp1971">{{cite journal | vauthors = Campaigne E, Knapp DR | title = Structural analogs of lysergic acid | journal = J Pharm Sci | volume = 60 | issue = 6 | pages = 809–814 | date = June 1971 | pmid = 4942861 | doi = 10.1002/jps.2600600602 | url = }}</ref><ref name="WO2021076572">{{cite patent | country = WO | number = 2021076572 | inventor = [[David E. Olson|Olsen DE]], Dunlap L, Wagner F, Chytil M, Powell NA | status = | title = Ergoline-like compounds for promoting neural plasticity | pubdate = 22 April 2021 | gdate = | fdate = 14 October 2020 | pridate = 14 October 2020 | assign1 = [[Delix Therapeutics, Inc.]] | assign2 = [[The Regents of the University of California]] | url =https://patents.google.com/patent/WO2021076572/ }}</ref> A notable [[bioisostere]] of LSD is [[JRT (drug)|JRT]], the [[isotryptamine]] analogue of LSD and a psychedelic and [[psychoplastogen]] under investigation to treat [[schizophrenia]].<ref name="TuckDunlapKhatib2025">{{cite journal | vauthors = Tuck JR, Dunlap LE, Khatib YA, Hatzipantelis CJ, Weiser Novak S, Rahn RM, Davis AR, Mosswood A, Vernier AM, Fenton EM, Aarrestad IK, Tombari RJ, Carter SJ, Deane Z, Wang Y, Sheridan A, Gonzalez MA, Avanes AA, Powell NA, Chytil M, Engel S, Fettinger JC, Jenkins AR, Carlezon WA, Nord AS, Kangas BD, Rasmussen K, Liston C, Manor U, Olson DE | title = Molecular design of a therapeutic LSD analogue with reduced hallucinogenic potential | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 122 | issue = 16 | pages = e2416106122 | date = April 2025 | pmid = 40228113 | doi = 10.1073/pnas.2416106122 | doi-access = free | pmc = 12037037 }}</ref><ref name="Dunlap2022">{{cite thesis | vauthors =  Dunlap L | degree = Ph.D. | publisher = University of California, Davis | chapter=Chapter 5. An Analog of LSD With Antipsychotic Potential | pages=105–114 | title=Development of Non-Hallucinogenic Psychoplastogens | date = 2022 | url=https://escholarship.org/content/qt5qr3w0gm/qt5qr3w0gm.pdf#page=112}}</ref>