Editing LSD (section)

===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>